Product Name

  • Name

    (3aR,4S,7R,7aS) 4,7-Methano-1H-isoindole-1,3(2H)-dione

  • EINECS 689-268-3
  • CAS No. 14805-29-9
  • Article Data10
  • CAS DataBase
  • Density 1.55 g/cm3
  • Solubility
  • Melting Point 173-176℃
  • Formula C9H11NO2
  • Boiling Point 519.7 °C at 760 mmHg
  • Molecular Weight 165.192
  • Flash Point 262.1 °C
  • Transport Information
  • Appearance white
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 14805-29-9 ((3aR,4S,7R,7aS) 4,7-Methano-1H-isoindole-1,3(2H)-dione)
  • Hazard Symbols
  • Synonyms 1H-4,7-Methanoisoindole-1,3(2H)-dione;NSC238001;AC1L8LM0;
  • PSA 46.17000
  • LogP 0.63390

Synthetic route

(1R,2S,6R,7S)-4-azatricyclo[5.2.1.0(2,6)]dec-8-ene-3,5-dione
6265-30-1

(1R,2S,6R,7S)-4-azatricyclo[5.2.1.0(2,6)]dec-8-ene-3,5-dione

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione
14805-29-9

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol Autoclave; Industrial scale;91.4%
exo-bicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride
14166-28-0

exo-bicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione
14805-29-9

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione

Conditions
ConditionsYield
With ammonium hydroxide In tetrahydrofuran at 190℃; for 2h;80.5%
Multi-step reaction with 2 steps
1: triethylamine / toluene / Reflux
2: pyridine / 0 - 20 °C
View Scheme
Stage #1: exo-bicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride In tetrahydrofuran at 25 - 35℃; for 0.166667h;
Stage #2: With ammonia In tetrahydrofuran; water at 0 - 35℃;
(1R,2R,6S,7S)-4-oxa-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
2746-19-2

(1R,2R,6S,7S)-4-oxa-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione
14805-29-9

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 95.9 percent / H2 / 10percent Pd/C / H2O; tetrahydrofuran / 1.5 h / Ambient temperature
2: 80.5 percent / 7percent aq. NH3 / tetrahydrofuran / 2 h / 190 °C
View Scheme
Multi-step reaction with 2 steps
1: 95.9 percent / H2 / 10percent Pd-C/ 50percent H2O / tetrahydrofuran / 1.5 h / Ambient temperature
2: 80.5 percent / 7percent aq. NH3 / tetrahydrofuran / 2 h / 190 °C
View Scheme
Multi-step reaction with 2 steps
1.1: palladium on activated charcoal; hydrogen / 25 - 35 °C / 3750.38 Torr / Inert atmosphere; Autoclave
2.1: tetrahydrofuran / 0.17 h / 25 - 35 °C
2.2: 0 - 35 °C
View Scheme
(3aR,4S,7R,7aS)-2-(((1R,2R)-2-(hydroxymethyl)cyclohexyl)methy)hexahydro-1H-4,7-methanoisoindole-1,3(2H)-dione

(3aR,4S,7R,7aS)-2-(((1R,2R)-2-(hydroxymethyl)cyclohexyl)methy)hexahydro-1H-4,7-methanoisoindole-1,3(2H)-dione

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione
14805-29-9

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione

Conditions
ConditionsYield
Stage #1: (3aR,4S,7R,7aS)-2-(((1R,2R)-2-(hydroxymethyl)cyclohexyl)methy)hexahydro-1H-4,7-methanoisoindole-1,3(2H)-dione; methanesulfonyl chloride With pyridine at 0 - 20℃;
Stage #2: With hydrogenchloride In water
cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione
14805-29-9

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 1 h / 200 °C
2.1: palladium on activated charcoal; hydrogen / 25 - 35 °C / 3750.38 Torr / Inert atmosphere; Autoclave
3.1: tetrahydrofuran / 0.17 h / 25 - 35 °C
3.2: 0 - 35 °C
View Scheme
3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione
14805-29-9

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ammonium acetate / 135 °C / Industrial scale
2: hydrogen; palladium 10% on activated carbon / methanol / Autoclave; Industrial scale
View Scheme
1,5-dibromo-pentane
111-24-0

1,5-dibromo-pentane

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione
14805-29-9

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione

N-(4-Bromopentyl)bicyclo<2.2.1>heptane-2,3-di-exo-carboximide
138274-10-9

N-(4-Bromopentyl)bicyclo<2.2.1>heptane-2,3-di-exo-carboximide

Conditions
ConditionsYield
With potassium carbonate In acetone Heating;100%
(1R,2R)-(-)-trans-cyclohexane-1,2-diylbis(methylene)dimethanesulfonate
186204-35-3

(1R,2R)-(-)-trans-cyclohexane-1,2-diylbis(methylene)dimethanesulfonate

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione
14805-29-9

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione

((1R,2R)-2-(((3aR,4S,7R,7aS)-1,3-dioxohexahydro-1H-4,7-methanoisoindol-2(3H)-yl)methyl)cyclohexyl)methylmethanesulfonate

((1R,2R)-2-(((3aR,4S,7R,7aS)-1,3-dioxohexahydro-1H-4,7-methanoisoindol-2(3H)-yl)methyl)cyclohexyl)methylmethanesulfonate

Conditions
ConditionsYield
With potassium carbonate In isopropyl alcohol for 4h;99%
(3aR,7aR)-4’-(benzo[d]isothiazol-3-yl)octahydrospiro[isoindole-2,1’-piperazin]-2-ium methanesulfonate
186204-37-5

(3aR,7aR)-4’-(benzo[d]isothiazol-3-yl)octahydrospiro[isoindole-2,1’-piperazin]-2-ium methanesulfonate

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione
14805-29-9

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione

(3aR,4S,7R,7aS)-2-[((1R,2R)-2-{[4-(l1,2-benzisothiazol-3-yl)piperazin-1-yl]methyl}cyclohexyl)methyl]hexahydro-1H-4,7-methanisoindol-1,3-dione hydrochloride
367514-88-3

(3aR,4S,7R,7aS)-2-[((1R,2R)-2-{[4-(l1,2-benzisothiazol-3-yl)piperazin-1-yl]methyl}cyclohexyl)methyl]hexahydro-1H-4,7-methanisoindol-1,3-dione hydrochloride

Conditions
ConditionsYield
Stage #1: (3aR,7aR)-4’-(benzo[d]isothiazol-3-yl)octahydrospiro[isoindole-2,1’-piperazin]-2-ium methanesulfonate; (3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione With potassium carbonate In toluene at 105℃; for 15h; Industrial scale;
Stage #2: With hydrogenchloride In isopropyl alcohol Industrial scale;		98.3%
Multi-step reaction with 2 steps
1.1: potassium carbonate; dibenzo-18-crown-6 / 5,5-dimethyl-1,3-cyclohexadiene / 3 h
2.1: methanol / 0.17 h / 60 - 65 °C
2.2: 1 h / 60 - 65 °C
View Scheme
C19H26N3S(1+)*CH3O3S(1-)

C19H26N3S(1+)*CH3O3S(1-)

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione
14805-29-9

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione

lurasidone

lurasidone

Conditions
ConditionsYield
With potassium carbonate In water for 10h; Reflux;95%
4-chlorobutyl bromide
6940-78-9

4-chlorobutyl bromide

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione
14805-29-9

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione

(3aR,4S,7R,7aS)-2-(4-chlorobutyl)hexahydro-1H-4,7-methanoisoindole-1,3(2H)-dione

(3aR,4S,7R,7aS)-2-(4-chlorobutyl)hexahydro-1H-4,7-methanoisoindole-1,3(2H)-dione

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃;95%
(3aR,7aR)-4’-(benzo[d]isothiazol-3-yl)octahydrospiro[isoindole-2,1’-piperazin]-2-ium methanesulfonate
186204-37-5

(3aR,7aR)-4’-(benzo[d]isothiazol-3-yl)octahydrospiro[isoindole-2,1’-piperazin]-2-ium methanesulfonate

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione
14805-29-9

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione

lurasidone

lurasidone

Conditions
ConditionsYield
With potassium carbonate In water; toluene for 8h; Product distribution / selectivity; Reflux;94.3%
With tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate In water for 3h; Product distribution / selectivity; Reflux;94.3%
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 36h; Temperature;91.8%
(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione
14805-29-9

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione

propargyl bromide
106-96-7

propargyl bromide

N-Propargylbicyclo<2.2.1>heptane-2,3-di-exo-carboximide
105981-36-0

N-Propargylbicyclo<2.2.1>heptane-2,3-di-exo-carboximide

Conditions
ConditionsYield
With potassium carbonate In acetone for 1h; Heating;91%
1,4-dibromo-butane
110-52-1

1,4-dibromo-butane

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione
14805-29-9

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione

(1R,2S,3R,4S)-N-(4-bromobutyl)-2,3-bicyclo<2.2.1>heptanedicarboximide
99095-09-7

(1R,2S,3R,4S)-N-(4-bromobutyl)-2,3-bicyclo<2.2.1>heptanedicarboximide

Conditions
ConditionsYield
With potassium carbonate In acetone for 7h; Heating;90.2%
(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione
14805-29-9

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione

1-chloro-3,4-epoxybutane
13067-79-3

1-chloro-3,4-epoxybutane

(1R,2S,3R,4S)-N-(3,4-epoxybutyl)-2,3-bicyclo<2.2.1>heptanedicarboxamide
105981-37-1

(1R,2S,3R,4S)-N-(3,4-epoxybutyl)-2,3-bicyclo<2.2.1>heptanedicarboxamide

Conditions
ConditionsYield
With potassium carbonate In acetone for 2h; Heating;90.1%
Z-1,4-dichlorobutene
1476-11-5

Z-1,4-dichlorobutene

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione
14805-29-9

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione

N-(4-Chloro-2-cis-butenyl)bicyclo<2.2.1>heptane-2,3-di-exo-carboximide
106035-14-7

N-(4-Chloro-2-cis-butenyl)bicyclo<2.2.1>heptane-2,3-di-exo-carboximide

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 90 - 100℃;90%
trans-1,4-dichlorobut-2-ene
110-57-6

trans-1,4-dichlorobut-2-ene

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione
14805-29-9

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione

N-(4-Chloro-2-trans-butenyl)bicyclo<2.2.1>heptane-2,3-di-exo-carboximide
105981-25-7

N-(4-Chloro-2-trans-butenyl)bicyclo<2.2.1>heptane-2,3-di-exo-carboximide

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 90 - 100℃; for 2h;88.7%
(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione
14805-29-9

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione

8-(1,2-benzisothiazol-3-yl)-2-methyl-8-aza-5-azoniaspiro<4,5>decane methanesulfonate

8-(1,2-benzisothiazol-3-yl)-2-methyl-8-aza-5-azoniaspiro<4,5>decane methanesulfonate

A

(1R,2S,3R,4S)-N-<4-<4-(1,2-benzisothiazol-3-yl)-1-piperazinyl>-2-methylbutyl>-2,3-bicyclo<2.2.1>heptanedicarboximide

(1R,2S,3R,4S)-N-<4-<4-(1,2-benzisothiazol-3-yl)-1-piperazinyl>-2-methylbutyl>-2,3-bicyclo<2.2.1>heptanedicarboximide

B

(1R,2S,3R,4S)-N-<4-<4-(1,2-benzisothiazol-3-yl)-1-piperazinyl>-3-methylbutyl>-2,3-bicyclo<2.2.1>heptanedicarboximide

(1R,2S,3R,4S)-N-<4-<4-(1,2-benzisothiazol-3-yl)-1-piperazinyl>-3-methylbutyl>-2,3-bicyclo<2.2.1>heptanedicarboximide

Conditions
ConditionsYield
With dibenzo-18-crown-6; potassium carbonate In xylene for 10h; Heating;A 17.2%
B 82.7%
...Expand
(3aR,7aR)-2,2-bis(2-hydroxyethyl)octahydro-1H-isoindolium mesylate
1421374-96-0

(3aR,7aR)-2,2-bis(2-hydroxyethyl)octahydro-1H-isoindolium mesylate

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione
14805-29-9

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione

(3aR,4S,7R,7aS)-2-(((1R,2R)-2-((bis(2-hydroxyethyl)amino)methyl)cyclohexyl)methyl)hexahydro-1H-4,7-methanoisoindole-1,3(2H)-dione

(3aR,4S,7R,7aS)-2-(((1R,2R)-2-((bis(2-hydroxyethyl)amino)methyl)cyclohexyl)methyl)hexahydro-1H-4,7-methanoisoindole-1,3(2H)-dione

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 16h;80%
8-(2-quinolinyl)-8-aza-5-azoniaspiro<4.5>decane bromide
142415-01-8

8-(2-quinolinyl)-8-aza-5-azoniaspiro<4.5>decane bromide

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione
14805-29-9

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione

(1S,2R,6S,7R)-4-[4-(4-Quinolin-2-yl-piperazin-1-yl)-butyl]-4-aza-tricyclo[5.2.1.02,6]decane-3,5-dione

(1S,2R,6S,7R)-4-[4-(4-Quinolin-2-yl-piperazin-1-yl)-butyl]-4-aza-tricyclo[5.2.1.02,6]decane-3,5-dione

Conditions
ConditionsYield
With potassium carbonate; 18-crown-6 ether In xylene for 6h; Heating;76%
4-(3,4-Epoxybutyl)-1-(2-pyrimidinyl)piperazine
138274-13-2

4-(3,4-Epoxybutyl)-1-(2-pyrimidinyl)piperazine

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione
14805-29-9

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione

(1R*,2S*,3R*,4S*)-N-<2-Hydroxy-4-<4-(2-pyrimidinyl)-1-piperazinyl>butyl>-2,3-bicyclo<2.2.1>heptanedicarboximide
138273-99-1

(1R*,2S*,3R*,4S*)-N-<2-Hydroxy-4-<4-(2-pyrimidinyl)-1-piperazinyl>butyl>-2,3-bicyclo<2.2.1>heptanedicarboximide

Conditions
ConditionsYield
With potassium carbonate In butan-1-ol for 6h; Heating;59%
(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione
14805-29-9

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione

3-<4-(3,4-epoxybutyl)-1-piperazinyl>-1,2-benzisothiazole

3-<4-(3,4-epoxybutyl)-1-piperazinyl>-1,2-benzisothiazole

(1R,2S,3R,4S)-N-<4-<4-(1,2-benzisothiazol-3-yl)-1-piperazinyl>-2-hydroxybutyl>-2,3-bicyclo<2.2.1>heptanedicarboximide

(1R,2S,3R,4S)-N-<4-<4-(1,2-benzisothiazol-3-yl)-1-piperazinyl>-2-hydroxybutyl>-2,3-bicyclo<2.2.1>heptanedicarboximide

Conditions
ConditionsYield
With potassium carbonate In butan-1-ol for 9h; Heating;47.7%
C21H29N3O5S2

C21H29N3O5S2

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione
14805-29-9

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione

C29H36N4O4S

C29H36N4O4S

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 133℃; for 2h; Molecular sieve;42%
1,4-dibromo-butane
110-52-1

1,4-dibromo-butane

N-(2-pyridinyl)piperazine
20980-22-7

N-(2-pyridinyl)piperazine

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione
14805-29-9

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione

tandospirone
87760-53-0

tandospirone

Conditions
ConditionsYield
With potassium carbonate; benzyltriethylammonium bromide 1.) toluene, reflux, 4 h, 2.) reflux, 5 h; Yield given. Multistep reaction;
...Expand
8-(2-Pyrimidinyl)-8-aza-5-azoniaspiro[4.5]decane Bromide
81461-73-6

8-(2-Pyrimidinyl)-8-aza-5-azoniaspiro[4.5]decane Bromide

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione
14805-29-9

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione

tandospirone
87760-53-0

tandospirone

Conditions
ConditionsYield
With potassium carbonate; 18-crown-6 ether In xylene for 6h; Heating;
(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione
14805-29-9

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione

(1S,2R,6S,7R)-4-{4-[4-(3-Chloro-pyridin-2-yl)-piperazin-1-yl]-butyl}-4-aza-tricyclo[5.2.1.02,6]decane-3,5-dione
106708-43-4

(1S,2R,6S,7R)-4-{4-[4-(3-Chloro-pyridin-2-yl)-piperazin-1-yl]-butyl}-4-aza-tricyclo[5.2.1.02,6]decane-3,5-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 90.2 percent / K2CO3 / acetone / 7 h / Heating
2: K2CO3, KI / acetonitrile / 8 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: 90.2 percent / K2CO3 / acetone / 7 h / Heating
2: 34 percent / K2CO3, KI / dimethylformamide / 90 °C
View Scheme
(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione
14805-29-9

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione

(1R*,2S*,6R*,7S*)-5-hydroxy-4-<4-<4-(1,2-benzisothiazol-3-yl)-1-piperazinyl>butyl>-4-azatricyclo<5.2.1.02,6>decan-3-one

(1R*,2S*,6R*,7S*)-5-hydroxy-4-<4-<4-(1,2-benzisothiazol-3-yl)-1-piperazinyl>butyl>-4-azatricyclo<5.2.1.02,6>decan-3-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 90.2 percent / K2CO3 / acetone / 7 h / Heating
2: K2CO3, KI / acetonitrile / 8 h / Heating
3: 63 percent / NaBH4, 0.1percent aq. NaOH / propan-2-ol / 2 h / Heating
View Scheme
(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione
14805-29-9

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione

(1R,2S,3R,4S)-N-<4-<4-(1,2-benzisothiazol-3-yl)-1-piperazinyl>-3-hydroxybutyl>-2,3-bicyclo<2.2.1>heptanedicarboximide

(1R,2S,3R,4S)-N-<4-<4-(1,2-benzisothiazol-3-yl)-1-piperazinyl>-3-hydroxybutyl>-2,3-bicyclo<2.2.1>heptanedicarboximide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 90.1 percent / K2CO3 / acetone / 2 h / Heating
2: 80.7 percent / butan-1-ol / 12 h / Heating
View Scheme
(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione
14805-29-9

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione

(1S,2R,6S,7R)-4-[4-(4-Oxo-1-phenyl-1,3,8-triaza-spiro[4.5]dec-8-yl)-butyl]-4-aza-tricyclo[5.2.1.02,6]decane-3,5-dione

(1S,2R,6S,7R)-4-[4-(4-Oxo-1-phenyl-1,3,8-triaza-spiro[4.5]dec-8-yl)-butyl]-4-aza-tricyclo[5.2.1.02,6]decane-3,5-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 90.2 percent / K2CO3 / acetone / 7 h / Heating
2: K2CO3, KI / acetonitrile / 8 h / Heating
View Scheme
(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione
14805-29-9

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione

(1S,2R,6S,7R)-4-{4-[4-(4-Chloro-phenyl)-4-hydroxy-piperidin-1-yl]-butyl}-4-aza-tricyclo[5.2.1.02,6]decane-3,5-dione

(1S,2R,6S,7R)-4-{4-[4-(4-Chloro-phenyl)-4-hydroxy-piperidin-1-yl]-butyl}-4-aza-tricyclo[5.2.1.02,6]decane-3,5-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 90.2 percent / K2CO3 / acetone / 7 h / Heating
2: 62.5 percent / K2CO3, KI / acetonitrile / 8 h / Heating
View Scheme
(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione
14805-29-9

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione

(1R,2S,3R,4S)-N-<4-<4-(1,2-benzisothiazol-3-yl)-1-piperazinyl>butyl>-2,3-bicyclo<2.2.1>heptanedicarboximide
106035-20-5

(1R,2S,3R,4S)-N-<4-<4-(1,2-benzisothiazol-3-yl)-1-piperazinyl>butyl>-2,3-bicyclo<2.2.1>heptanedicarboximide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 90.2 percent / K2CO3 / acetone / 7 h / Heating
2: K2CO3, KI / acetonitrile / 8 h / Heating
View Scheme
(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione
14805-29-9

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione

(1S,2R,6S,7R)-4-{4-[4-(2-Oxo-2,3-dihydro-benzoimidazol-1-yl)-piperidin-1-yl]-butyl}-4-aza-tricyclo[5.2.1.02,6]decane-3,5-dione

(1S,2R,6S,7R)-4-{4-[4-(2-Oxo-2,3-dihydro-benzoimidazol-1-yl)-piperidin-1-yl]-butyl}-4-aza-tricyclo[5.2.1.02,6]decane-3,5-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 90.2 percent / K2CO3 / acetone / 7 h / Heating
2: 66.4 percent / K2CO3, KI / acetonitrile / 8 h / Heating
View Scheme
(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione
14805-29-9

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione

N-<4-(3-Methyl-1-piperazinyl)butyl>bicyclo<2.2.1>heptane-2,3-di-exo-carboximide
138274-11-0

N-<4-(3-Methyl-1-piperazinyl)butyl>bicyclo<2.2.1>heptane-2,3-di-exo-carboximide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 90.2 percent / K2CO3 / acetone / 7 h / Heating
2: 100 percent / ethanol / Ambient temperature
View Scheme

(3aR,4S,7R,7aS) 4,7-Methano-1H-isoindole-1,3(2H)-dione Specification

The (3aR,4S,7R,7aS) 4,7-Methano-1H-isoindole-1,3(2H)-dione with CAS registry number of 14805-29-9 is also known as NSC238001. The systematic name is 1H-4,7-Methanoisoindole-1,3(2H)-dione. In addition, the formula is C9H11NO2 and the molecular weight is 159.14.

Physical properties about (3aR,4S,7R,7aS) 4,7-Methano-1H-isoindole-1,3(2H)-dione are: (1)ACD/LogP: 0.29; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.29; (4)ACD/LogD (pH 7.4): 0.28; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 34.2; (8)ACD/KOC (pH 7.4): 33.81; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)Index of Refraction: 1.714; (12)Molar Refractivity: 40.28 cm3; (13)Molar Volume: 102.6 cm3; (14)Surface Tension: 62.4 dyne/cm; (15)Density: 1.55 g/cm3; (16)Flash Point: 262.1 °C; (17)Enthalpy of Vaporization: 79.25 kJ/mol; (18)Boiling Point: 519.7 °C at 760 mmHg; (19)Vapour Pressure: 6.67E-11 mmHg at 25 °C.

Preparation of (3aR,4S,7R,7aS) 4,7-Methano-1H-isoindole-1,3(2H)-dione: it is prepared by reaction of norbornane-2exo,3exo-dicarboxylic acid-anhydride. The reaction needs reagent 7percent aq. NH3 and solvent tetrahydrofuran at the temperature of 190 °C for 2 hours. The yield is about 80.5%.

(3aR,4S,7R,7aS) 4,7-Methano-1H-isoindole-1,3(2H)-dione is prepared by reaction of norbornane-2exo,3exo-dicarboxylic acid-anhydride.

Uses of (3aR,4S,7R,7aS) 4,7-Methano-1H-isoindole-1,3(2H)-dione: it is used to produce N-(4-bromobutyl)bicyclo[2.2.1]heptane-2,3-di-exo-carboximide by reaction with 1,4-dibromo-butane. The reaction occurs with reagent K2CO3 and solvent acetone with other condition of heating for 7 hours. The yield is about 90.2%.

(3aR,4S,7R,7aS) 4,7-Methano-1H-isoindole-1,3(2H)-dione is used to produce N-(4-bromobutyl)bicyclo[2.2.1]heptane-2,3-di-exo-carboximide by reaction with 1,4-dibromo-butane.

You can still convert the following datas into molecular structure:
1. SMILES: O=C2NC(=O)C=3\C\1=C\C=C(/C/1)\C2=3
2. InChI: InChI=1/C9H5NO2/c11-8-6-4-1-2-5(3-4)7(6)9(12)10-8/h1-2H,3H2,(H,10,11,12)
3. InChIKey: STMLHNAVHHLFKU-UHFFFAOYAK
4. Std. InChI: InChI=1S/C9H5NO2/c11-8-6-4-1-2-5(3-4)7(6)9(12)10-8/h1-2H,3H2,(H,10,11,12)
5. Std. InChIKey: STMLHNAVHHLFKU-UHFFFAOYSA-N

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