Product Name

  • Name

    (+/-)-2-ACETYL-9-AZA BICYCLO[4.2.1]NON-2-ENE FUMARATE

  • EINECS
  • CAS No. 64285-06-9
  • Article Data11
  • CAS DataBase
  • Density 1.037 g/cm3
  • Solubility Soluble to 50 mM in Water
  • Melting Point
  • Formula C10H15 N O
  • Boiling Point 291 °C at 760 mmHg
  • Molecular Weight 165.235
  • Flash Point 124.7 °C
  • Transport Information
  • Appearance Lyophilized Solid
  • Safety Poison by intraperitoneal route. An experimental teratogen. When heated to decomposition it emits toxic fumes of NOx.
  • Risk Codes
  • Molecular Structure Molecular Structure of 64285-06-9 ((+/-)-2-ACETYL-9-AZA BICYCLO[4.2.1]NON-2-ENE FUMARATE)
  • Hazard Symbols
  • Synonyms Ethanone,1-(9-azabicyclo[4.2.1]non-2-en-2-yl)-, (1R)-; 9-Azabicyclo[4.2.1]nonane,ethanone deriv.; (+)-Anatoxin a; (+)-Anatoxin a; (+)-Anatoxin-a; Anatoxin I; Anatoxin a; Anatoxin a
  • PSA 29.10000
  • LogP 1.74500

Synthetic route

(+)-(1R)-2-acetyl-9-benzyloxycarbonyl-9-azabicyclo[4.2.1]-2-nonene
120692-41-3

(+)-(1R)-2-acetyl-9-benzyloxycarbonyl-9-azabicyclo[4.2.1]-2-nonene

anatoxin-a
64285-06-9

anatoxin-a

Conditions
ConditionsYield
With trimethylsilyl iodide In acetonitrile at -10℃; for 0.333333h;99%
(-)-N-tosylanatoxin-a
143264-77-1

(-)-N-tosylanatoxin-a

anatoxin-a
64285-06-9

anatoxin-a

Conditions
ConditionsYield
With disodium hydrogenphosphate; sodium amalgam In methanol at -40℃; for 0.166667h;76%
(1R,6R)-2-Acetyl-9-aza-bicyclo[4.2.1]non-2-ene-9-carboxylic acid vinyl ester
216166-93-7

(1R,6R)-2-Acetyl-9-aza-bicyclo[4.2.1]non-2-ene-9-carboxylic acid vinyl ester

anatoxin-a
64285-06-9

anatoxin-a

Conditions
ConditionsYield
With hydrochloric acid diethyl ether In ethanol at 50℃;
methyl (2R)-pyroglutamate
64700-65-8

methyl (2R)-pyroglutamate

anatoxin-a
64285-06-9

anatoxin-a

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: 100 percent / LiHMDS / tetrahydrofuran / -78 - 20 °C
2.1: Mg / tetrahydrofuran / 0.83 h / 20 °C
2.2: 73 percent / TMEDA / tetrahydrofuran / 1.5 h / -78 °C
3.1: BF3*OEt2; Ph3SiH / CH2Cl2 / 2.5 h / -78 - 20 °C
3.2: DIBAL-H / toluene / 3 h / -78 °C
3.3: 826 mg / Cs2CO3 / toluene; propan-2-ol / 17 h / 20 °C
4.1: 97 percent / NaHMDS / tetrahydrofuran / 2 h / -78 °C
5.1: 84 percent / second generation Grubbs catalyst / CH2Cl2 / 16 h
6.1: 76 percent / Et3N; OsO4 / tetrahydrofuran / 22 h / -78 - 20 °C
7.1: 95 percent / NaIO4 / tetrahydrofuran; H2O / 1.5 h / 20 °C
8.1: 99 percent / TMSI / acetonitrile / 0.33 h / -10 °C
View Scheme
1-benzyl 2-methyl (R)-5-oxopyrrolidine-1,2-dicarboxylate
690211-34-8

1-benzyl 2-methyl (R)-5-oxopyrrolidine-1,2-dicarboxylate

anatoxin-a
64285-06-9

anatoxin-a

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: Mg / tetrahydrofuran / 0.83 h / 20 °C
1.2: 73 percent / TMEDA / tetrahydrofuran / 1.5 h / -78 °C
2.1: BF3*OEt2; Ph3SiH / CH2Cl2 / 2.5 h / -78 - 20 °C
2.2: DIBAL-H / toluene / 3 h / -78 °C
2.3: 826 mg / Cs2CO3 / toluene; propan-2-ol / 17 h / 20 °C
3.1: 97 percent / NaHMDS / tetrahydrofuran / 2 h / -78 °C
4.1: 84 percent / second generation Grubbs catalyst / CH2Cl2 / 16 h
5.1: 76 percent / Et3N; OsO4 / tetrahydrofuran / 22 h / -78 - 20 °C
6.1: 95 percent / NaIO4 / tetrahydrofuran; H2O / 1.5 h / 20 °C
7.1: 99 percent / TMSI / acetonitrile / 0.33 h / -10 °C
View Scheme
(2R,5R)-5-but-3-enyl-2-ethynylpyrrolidine-1-carboxylic acid 1-benzyl ester
690211-37-1

(2R,5R)-5-but-3-enyl-2-ethynylpyrrolidine-1-carboxylic acid 1-benzyl ester

anatoxin-a
64285-06-9

anatoxin-a

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 97 percent / NaHMDS / tetrahydrofuran / 2 h / -78 °C
2: 84 percent / second generation Grubbs catalyst / CH2Cl2 / 16 h
3: 76 percent / Et3N; OsO4 / tetrahydrofuran / 22 h / -78 - 20 °C
4: 95 percent / NaIO4 / tetrahydrofuran; H2O / 1.5 h / 20 °C
5: 99 percent / TMSI / acetonitrile / 0.33 h / -10 °C
View Scheme
(2R)-but-3-enyl-(5R)-prop-1-ynylpyrrolidine-1-carboxylic acid 1-benzyl ester
690211-38-2

(2R)-but-3-enyl-(5R)-prop-1-ynylpyrrolidine-1-carboxylic acid 1-benzyl ester

anatoxin-a
64285-06-9

anatoxin-a

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 84 percent / second generation Grubbs catalyst / CH2Cl2 / 16 h
2: 76 percent / Et3N; OsO4 / tetrahydrofuran / 22 h / -78 - 20 °C
3: 95 percent / NaIO4 / tetrahydrofuran; H2O / 1.5 h / 20 °C
4: 99 percent / TMSI / acetonitrile / 0.33 h / -10 °C
View Scheme
(+)-(1R)-2-isopropenyl-9-benzyloxycarbonyl-9-azabicyclo[4.2.1]-2-nonene
690211-39-3

(+)-(1R)-2-isopropenyl-9-benzyloxycarbonyl-9-azabicyclo[4.2.1]-2-nonene

anatoxin-a
64285-06-9

anatoxin-a

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 76 percent / Et3N; OsO4 / tetrahydrofuran / 22 h / -78 - 20 °C
2: 95 percent / NaIO4 / tetrahydrofuran; H2O / 1.5 h / 20 °C
3: 99 percent / TMSI / acetonitrile / 0.33 h / -10 °C
View Scheme
(2R)-benzyloxycarbonylamino-5-oxonon-8-enoic acid methyl ester
690211-35-9

(2R)-benzyloxycarbonylamino-5-oxonon-8-enoic acid methyl ester

anatoxin-a
64285-06-9

anatoxin-a

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: BF3*OEt2; Ph3SiH / CH2Cl2 / 2.5 h / -78 - 20 °C
1.2: DIBAL-H / toluene / 3 h / -78 °C
1.3: 826 mg / Cs2CO3 / toluene; propan-2-ol / 17 h / 20 °C
2.1: 97 percent / NaHMDS / tetrahydrofuran / 2 h / -78 °C
3.1: 84 percent / second generation Grubbs catalyst / CH2Cl2 / 16 h
4.1: 76 percent / Et3N; OsO4 / tetrahydrofuran / 22 h / -78 - 20 °C
5.1: 95 percent / NaIO4 / tetrahydrofuran; H2O / 1.5 h / 20 °C
6.1: 99 percent / TMSI / acetonitrile / 0.33 h / -10 °C
View Scheme
(+)-(1R)-2-(1,2-dihydroxy-1-methylethyl)-9-benzyloxycarbonyl-9-azabicyclo[4.2.1]-2-nonene
690211-40-6

(+)-(1R)-2-(1,2-dihydroxy-1-methylethyl)-9-benzyloxycarbonyl-9-azabicyclo[4.2.1]-2-nonene

anatoxin-a
64285-06-9

anatoxin-a

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 95 percent / NaIO4 / tetrahydrofuran; H2O / 1.5 h / 20 °C
2: 99 percent / TMSI / acetonitrile / 0.33 h / -10 °C
View Scheme
(2R)-but-3-enyl-(5R)-2-(1-methylsiletan-1-ylethynyl)pyrrolidine-1-carboxylic acid benzyl ester
760968-59-0

(2R)-but-3-enyl-(5R)-2-(1-methylsiletan-1-ylethynyl)pyrrolidine-1-carboxylic acid benzyl ester

anatoxin-a
64285-06-9

anatoxin-a

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 9 percent / second generation Grubbs catalyst / CH2Cl2 / 80 °C
2: 97 percent / NaHMDS / tetrahydrofuran / 2 h / -78 °C
3: 84 percent / second generation Grubbs catalyst / CH2Cl2 / 16 h
4: 76 percent / Et3N; OsO4 / tetrahydrofuran / 22 h / -78 - 20 °C
5: 95 percent / NaIO4 / tetrahydrofuran; H2O / 1.5 h / 20 °C
6: 99 percent / TMSI / acetonitrile / 0.33 h / -10 °C
View Scheme
(1R)-9-methyl-9-azabicyclo[4.2.1]nonan-2-one
126811-06-1

(1R)-9-methyl-9-azabicyclo[4.2.1]nonan-2-one

anatoxin-a
64285-06-9

anatoxin-a

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: LiN(SiMe3)2 / tetrahydrofuran / -40 °C
2: 95 percent / K2CO3 / CH2Cl2 / Heating
3: AlCl3 / 1,2-dichloro-ethane / -10 °C
4: 65 percent / LiBr, Li2CO3 / dimethylformamide / 150 °C
5: HCl*Et2O / ethanol / 50 °C
View Scheme
C12H18N2O

C12H18N2O

anatoxin-a
64285-06-9

anatoxin-a

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 95 percent / K2CO3 / CH2Cl2 / Heating
2: AlCl3 / 1,2-dichloro-ethane / -10 °C
3: 65 percent / LiBr, Li2CO3 / dimethylformamide / 150 °C
4: HCl*Et2O / ethanol / 50 °C
View Scheme
(1R,2S,6R)-2-Acetyl-2-chloro-9-aza-bicyclo[4.2.1]nonane-9-carboxylic acid vinyl ester

(1R,2S,6R)-2-Acetyl-2-chloro-9-aza-bicyclo[4.2.1]nonane-9-carboxylic acid vinyl ester

anatoxin-a
64285-06-9

anatoxin-a

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 65 percent / LiBr, Li2CO3 / dimethylformamide / 150 °C
2: HCl*Et2O / ethanol / 50 °C
View Scheme
C14H18N2O3

C14H18N2O3

anatoxin-a
64285-06-9

anatoxin-a

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: AlCl3 / 1,2-dichloro-ethane / -10 °C
2: 65 percent / LiBr, Li2CO3 / dimethylformamide / 150 °C
3: HCl*Et2O / ethanol / 50 °C
View Scheme
(-)-(5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-1-tosylpyrrolidin-2-one
132974-84-6

(-)-(5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-1-tosylpyrrolidin-2-one

anatoxin-a
64285-06-9

anatoxin-a

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 92 percent / DIBAL / CH2Cl2 / -78 °C
2: 87 percent / PPTS / methanol
3: 96 percent / Bu4NF / tetrahydrofuran
4: 1.) BuLi / 1.) THF, -78 deg C
5: toluene / Irradiation
6: 1.) O3, 2.) Me2S / 1.) CH2Cl2, -78 deg C
7: 79 percent / NaH / tetrahydrofuran
8: 1.) HCl, 2.) DBU / 1.) CH2Cl2, MeOH, 2.) toluene, reflux
9: 76 percent / Na(Hg), Na2HPO4 / methanol / 0.17 h / -40 °C
View Scheme
Multi-step reaction with 12 steps
1: 92 percent / DIBAL / CH2Cl2 / -78 °C
2: 87 percent / PPTS / methanol
3: 96 percent / Bu4NF / tetrahydrofuran
4: 1.) BuLi / 1.) THF, -78 deg C
5: toluene / Irradiation
6: 1.) BH3*DMS, 2.) H2O2, 6M NaOH / 1.) THF
7: 1.) (COCl)2, 2.) Et3N / 1.) DMSO, 2.) CH2Cl2, -78 deg C
8: tetrahydrofuran
9: 76 percent / TiCl4 / CH2Cl2 / -78 °C
10: 71 percent / O2 / PdCl2, CuCl / dimethylformamide; H2O
11: 1.) KH, TMSCl, 2.) Et3N / 2.) Pd(OAc)2 / 2.) CH3CN
12: 76 percent / Na(Hg), Na2HPO4 / methanol / 0.17 h / -40 °C
View Scheme
[(2S,5R)-5-Methoxy-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-methanol
143264-74-8

[(2S,5R)-5-Methoxy-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-methanol

anatoxin-a
64285-06-9

anatoxin-a

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 1.) BuLi / 1.) THF, -78 deg C
2: toluene / Irradiation
3: 1.) O3, 2.) Me2S / 1.) CH2Cl2, -78 deg C
4: 79 percent / NaH / tetrahydrofuran
5: 1.) HCl, 2.) DBU / 1.) CH2Cl2, MeOH, 2.) toluene, reflux
6: 76 percent / Na(Hg), Na2HPO4 / methanol / 0.17 h / -40 °C
View Scheme
Multi-step reaction with 9 steps
1: 1.) BuLi / 1.) THF, -78 deg C
2: toluene / Irradiation
3: 1.) BH3*DMS, 2.) H2O2, 6M NaOH / 1.) THF
4: 1.) (COCl)2, 2.) Et3N / 1.) DMSO, 2.) CH2Cl2, -78 deg C
5: tetrahydrofuran
6: 76 percent / TiCl4 / CH2Cl2 / -78 °C
7: 71 percent / O2 / PdCl2, CuCl / dimethylformamide; H2O
8: 1.) KH, TMSCl, 2.) Et3N / 2.) Pd(OAc)2 / 2.) CH3CN
9: 76 percent / Na(Hg), Na2HPO4 / methanol / 0.17 h / -40 °C
View Scheme
(2R,5R)-2-But-3-enyl-5-methoxy-1-(toluene-4-sulfonyl)-pyrrolidine
143264-75-9

(2R,5R)-2-But-3-enyl-5-methoxy-1-(toluene-4-sulfonyl)-pyrrolidine

anatoxin-a
64285-06-9

anatoxin-a

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.) O3, 2.) Me2S / 1.) CH2Cl2, -78 deg C
2: 79 percent / NaH / tetrahydrofuran
3: 1.) HCl, 2.) DBU / 1.) CH2Cl2, MeOH, 2.) toluene, reflux
4: 76 percent / Na(Hg), Na2HPO4 / methanol / 0.17 h / -40 °C
View Scheme
Multi-step reaction with 7 steps
1: 1.) BH3*DMS, 2.) H2O2, 6M NaOH / 1.) THF
2: 1.) (COCl)2, 2.) Et3N / 1.) DMSO, 2.) CH2Cl2, -78 deg C
3: tetrahydrofuran
4: 76 percent / TiCl4 / CH2Cl2 / -78 °C
5: 71 percent / O2 / PdCl2, CuCl / dimethylformamide; H2O
6: 1.) KH, TMSCl, 2.) Et3N / 2.) Pd(OAc)2 / 2.) CH3CN
7: 76 percent / Na(Hg), Na2HPO4 / methanol / 0.17 h / -40 °C
View Scheme
(1R,6R)-9-(Toluene-4-sulfonyl)-2-vinyl-9-aza-bicyclo[4.2.1]nonane
143264-80-6

(1R,6R)-9-(Toluene-4-sulfonyl)-2-vinyl-9-aza-bicyclo[4.2.1]nonane

anatoxin-a
64285-06-9

anatoxin-a

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 71 percent / O2 / PdCl2, CuCl / dimethylformamide; H2O
2: 1.) KH, TMSCl, 2.) Et3N / 2.) Pd(OAc)2 / 2.) CH3CN
3: 76 percent / Na(Hg), Na2HPO4 / methanol / 0.17 h / -40 °C
View Scheme
3-[(2S,5R)-5-Methoxy-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionaldehyde

3-[(2S,5R)-5-Methoxy-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionaldehyde

anatoxin-a
64285-06-9

anatoxin-a

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 79 percent / NaH / tetrahydrofuran
2: 1.) HCl, 2.) DBU / 1.) CH2Cl2, MeOH, 2.) toluene, reflux
3: 76 percent / Na(Hg), Na2HPO4 / methanol / 0.17 h / -40 °C
View Scheme
4-[(2R,5R)-5-Methoxy-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-butan-1-ol
143264-78-2

4-[(2R,5R)-5-Methoxy-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-butan-1-ol

anatoxin-a
64285-06-9

anatoxin-a

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 1.) (COCl)2, 2.) Et3N / 1.) DMSO, 2.) CH2Cl2, -78 deg C
2: tetrahydrofuran
3: 76 percent / TiCl4 / CH2Cl2 / -78 °C
4: 71 percent / O2 / PdCl2, CuCl / dimethylformamide; H2O
5: 1.) KH, TMSCl, 2.) Et3N / 2.) Pd(OAc)2 / 2.) CH3CN
6: 76 percent / Na(Hg), Na2HPO4 / methanol / 0.17 h / -40 °C
View Scheme
1-[(1R,6R)-9-(Toluene-4-sulfonyl)-9-aza-bicyclo[4.2.1]non-2-yl]-ethanone

1-[(1R,6R)-9-(Toluene-4-sulfonyl)-9-aza-bicyclo[4.2.1]non-2-yl]-ethanone

anatoxin-a
64285-06-9

anatoxin-a

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) KH, TMSCl, 2.) Et3N / 2.) Pd(OAc)2 / 2.) CH3CN
2: 76 percent / Na(Hg), Na2HPO4 / methanol / 0.17 h / -40 °C
View Scheme
4-[(2R,5R)-5-Methoxy-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-butyraldehyde

4-[(2R,5R)-5-Methoxy-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-butyraldehyde

anatoxin-a
64285-06-9

anatoxin-a

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: tetrahydrofuran
2: 76 percent / TiCl4 / CH2Cl2 / -78 °C
3: 71 percent / O2 / PdCl2, CuCl / dimethylformamide; H2O
4: 1.) KH, TMSCl, 2.) Et3N / 2.) Pd(OAc)2 / 2.) CH3CN
5: 76 percent / Na(Hg), Na2HPO4 / methanol / 0.17 h / -40 °C
View Scheme
(E)-6-[(2R,5R)-5-Methoxy-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-hex-3-en-2-one
143264-76-0, 143292-29-9

(E)-6-[(2R,5R)-5-Methoxy-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-hex-3-en-2-one

anatoxin-a
64285-06-9

anatoxin-a

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) HCl, 2.) DBU / 1.) CH2Cl2, MeOH, 2.) toluene, reflux
2: 76 percent / Na(Hg), Na2HPO4 / methanol / 0.17 h / -40 °C
View Scheme
(2R,5R)-2-Methoxy-1-(toluene-4-sulfonyl)-5-((E)-5-trimethylsilanyl-pent-4-enyl)-pyrrolidine
143264-79-3, 143292-31-3

(2R,5R)-2-Methoxy-1-(toluene-4-sulfonyl)-5-((E)-5-trimethylsilanyl-pent-4-enyl)-pyrrolidine

anatoxin-a
64285-06-9

anatoxin-a

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 76 percent / TiCl4 / CH2Cl2 / -78 °C
2: 71 percent / O2 / PdCl2, CuCl / dimethylformamide; H2O
3: 1.) KH, TMSCl, 2.) Et3N / 2.) Pd(OAc)2 / 2.) CH3CN
4: 76 percent / Na(Hg), Na2HPO4 / methanol / 0.17 h / -40 °C
View Scheme
Thiocarbonic acid O-[(2S,5R)-5-methoxy-1-(toluene-4-sulfonyl)-pyrrolidin-2-ylmethyl] ester O-phenyl ester

Thiocarbonic acid O-[(2S,5R)-5-methoxy-1-(toluene-4-sulfonyl)-pyrrolidin-2-ylmethyl] ester O-phenyl ester

anatoxin-a
64285-06-9

anatoxin-a

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: toluene / Irradiation
2: 1.) O3, 2.) Me2S / 1.) CH2Cl2, -78 deg C
3: 79 percent / NaH / tetrahydrofuran
4: 1.) HCl, 2.) DBU / 1.) CH2Cl2, MeOH, 2.) toluene, reflux
5: 76 percent / Na(Hg), Na2HPO4 / methanol / 0.17 h / -40 °C
View Scheme
Multi-step reaction with 8 steps
1: toluene / Irradiation
2: 1.) BH3*DMS, 2.) H2O2, 6M NaOH / 1.) THF
3: 1.) (COCl)2, 2.) Et3N / 1.) DMSO, 2.) CH2Cl2, -78 deg C
4: tetrahydrofuran
5: 76 percent / TiCl4 / CH2Cl2 / -78 °C
6: 71 percent / O2 / PdCl2, CuCl / dimethylformamide; H2O
7: 1.) KH, TMSCl, 2.) Et3N / 2.) Pd(OAc)2 / 2.) CH3CN
8: 76 percent / Na(Hg), Na2HPO4 / methanol / 0.17 h / -40 °C
View Scheme
N-p-toluenesulphonyl(5-diphenyl-tert-butylsilyloxymethyl)-2-hydroxypyrrolidine
143264-72-6, 143292-32-4

N-p-toluenesulphonyl(5-diphenyl-tert-butylsilyloxymethyl)-2-hydroxypyrrolidine

anatoxin-a
64285-06-9

anatoxin-a

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 87 percent / PPTS / methanol
2: 96 percent / Bu4NF / tetrahydrofuran
3: 1.) BuLi / 1.) THF, -78 deg C
4: toluene / Irradiation
5: 1.) O3, 2.) Me2S / 1.) CH2Cl2, -78 deg C
6: 79 percent / NaH / tetrahydrofuran
7: 1.) HCl, 2.) DBU / 1.) CH2Cl2, MeOH, 2.) toluene, reflux
8: 76 percent / Na(Hg), Na2HPO4 / methanol / 0.17 h / -40 °C
View Scheme
Multi-step reaction with 11 steps
1: 87 percent / PPTS / methanol
2: 96 percent / Bu4NF / tetrahydrofuran
3: 1.) BuLi / 1.) THF, -78 deg C
4: toluene / Irradiation
5: 1.) BH3*DMS, 2.) H2O2, 6M NaOH / 1.) THF
6: 1.) (COCl)2, 2.) Et3N / 1.) DMSO, 2.) CH2Cl2, -78 deg C
7: tetrahydrofuran
8: 76 percent / TiCl4 / CH2Cl2 / -78 °C
9: 71 percent / O2 / PdCl2, CuCl / dimethylformamide; H2O
10: 1.) KH, TMSCl, 2.) Et3N / 2.) Pd(OAc)2 / 2.) CH3CN
11: 76 percent / Na(Hg), Na2HPO4 / methanol / 0.17 h / -40 °C
View Scheme
N-p-toluenesulphonyl(5-diphenyl-tert-butylsilyloxymethyl)-2-methoxypyrrolidine
143264-73-7, 143292-30-2

N-p-toluenesulphonyl(5-diphenyl-tert-butylsilyloxymethyl)-2-methoxypyrrolidine

anatoxin-a
64285-06-9

anatoxin-a

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 96 percent / Bu4NF / tetrahydrofuran
2: 1.) BuLi / 1.) THF, -78 deg C
3: toluene / Irradiation
4: 1.) O3, 2.) Me2S / 1.) CH2Cl2, -78 deg C
5: 79 percent / NaH / tetrahydrofuran
6: 1.) HCl, 2.) DBU / 1.) CH2Cl2, MeOH, 2.) toluene, reflux
7: 76 percent / Na(Hg), Na2HPO4 / methanol / 0.17 h / -40 °C
View Scheme
Multi-step reaction with 10 steps
1: 96 percent / Bu4NF / tetrahydrofuran
2: 1.) BuLi / 1.) THF, -78 deg C
3: toluene / Irradiation
4: 1.) BH3*DMS, 2.) H2O2, 6M NaOH / 1.) THF
5: 1.) (COCl)2, 2.) Et3N / 1.) DMSO, 2.) CH2Cl2, -78 deg C
6: tetrahydrofuran
7: 76 percent / TiCl4 / CH2Cl2 / -78 °C
8: 71 percent / O2 / PdCl2, CuCl / dimethylformamide; H2O
9: 1.) KH, TMSCl, 2.) Et3N / 2.) Pd(OAc)2 / 2.) CH3CN
10: 76 percent / Na(Hg), Na2HPO4 / methanol / 0.17 h / -40 °C
View Scheme
anatoxin-a
64285-06-9

anatoxin-a

L-N-Boc-Ala
15761-38-3

L-N-Boc-Ala

(S)-Ala-(1R)-anatoxin

(S)-Ala-(1R)-anatoxin

Anatoxin I Chemical Properties

IUPAC Name: 1-[(1R,6R)-9-Azabicyclo[4.2.1]non-4-en-5-yl]ethanone
Synonyms: (1R)-ethanon;anatoxini ; (+/-)-Anatoxin a ; (+/-)-Anatoxin a fumarate ; (+/-)-Anatoxin a fumerate ; (+/-)-2-Acetyl-9-aza bicyclo[4.2.1]non-2-ene fumarate ; (-)-Anatoxin ; (1β,6β)-5-Acetyl-9-azabicyclo[4.2.1]non-4-ene
Product Categories: Acetylcholine receptor
CAS NO: 64285-06-9
Molecular Formula of Anatoxin I (CAS NO.64285-06-9) : C10H15NO
Molecular Weight of Anatoxin I (CAS NO.64285-06-9) : 165.23
Molecular Structure of Anatoxin I (CAS NO.64285-06-9) :
Mol File: 64285-06-9.mol
Index of Refraction: 1.503
Surface Tension: 34 dyne/cm
Density: 1.037 g/cm3
Flash Point: 124.7 °C
Enthalpy of Vaporization: 53.04 kJ/mol
Boiling Point: 291 °C at 760 mmHg
Vapour Pressure: 0.002 mmHg at 25°C

Anatoxin I Toxicity Data With Reference

1.    

ipr-mus LDLo:250 µg/kg

     TOXIA6    Toxicon. 27 (1989),79.

Anatoxin I Safety Profile

Poison by intraperitoneal route. An experimental teratogen. When heated to decomposition it emits toxic fumes of NOx.

Anatoxin I Specification

Category: Toxic Substances
Toxicity classification: highly toxic
Acute toxicity: abdominal - mice LDL0: 0.25 mg / kg
Flammable hazardous characteristics: flammable; burning of toxic nitrogen oxide fumes
Storage features: Treasury ventilation, low temperature, dry
Fire-extinguishing agents: water, carbon dioxide, dry powder, sand

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