Product Name

  • Name

    (1R,4S)-4-Amino-cyclopent-2-enecarboxylic acid hydrochloride

  • EINECS
  • CAS No. 130931-85-0
  • Article Data4
  • CAS DataBase
  • Density
  • Solubility
  • Melting Point
  • Formula C6H10ClNO2
  • Boiling Point 266.6 °C at 760 mmHg
  • Molecular Weight 163.604
  • Flash Point 115 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 130931-85-0 ((1R,4S)-4-Amino-cyclopent-2-enecarboxylic acid hydrochloride)
  • Hazard Symbols
  • Synonyms (1R,4S)-4-AMINO-CYCLOPENT-2-ENECARBOXYLIC ACID HYDROCHLORIDE
  • PSA 63.32000
  • LogP 1.47670

Synthetic route

(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one
130931-83-8

(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride
130931-85-0

(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In water for 2h; Reflux;90%
(-)-[(1R,4S)-tert-butyl 3-oxo-2-azabicyclo(2.2.1)hept-5-ene-2-carboxylate]
200002-41-1

(-)-[(1R,4S)-tert-butyl 3-oxo-2-azabicyclo(2.2.1)hept-5-ene-2-carboxylate]

(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride
130931-85-0

(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In water for 2h; Reflux;82%
(1R,4S)-4-[(tert-butoxycarbonyl)amino]cyclopent-2-ene-1-carboxylic acid
151907-80-1

(1R,4S)-4-[(tert-butoxycarbonyl)amino]cyclopent-2-ene-1-carboxylic acid

(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride
130931-85-0

(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane at 20℃; for 2h;
racemic N-hydroxymethyl vince lactam

racemic N-hydroxymethyl vince lactam

(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride
130931-85-0

(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: water; lipase B from Candida antarctica; benzylamine / isopropyl alcohol / 0.5 h / 60 °C / Enzymatic reaction
2: hydrogenchloride; water / 5 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: water; lipase B from Candida antarctica; benzylamine / isopropyl alcohol / 2 h / 60 °C / Enzymatic reaction
2: hydrogenchloride; water / 5 h / Reflux
View Scheme
(1S,4R)-N-hydroxymethyl-2-azabicyclo<2.2.1>hept-5-en-3-one
157810-20-3

(1S,4R)-N-hydroxymethyl-2-azabicyclo<2.2.1>hept-5-en-3-one

(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride
130931-85-0

(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; water for 5h; Reflux;
racemic 2-azabicyclo[2.2.1]hept-5-en-3-one
49805-30-3

racemic 2-azabicyclo[2.2.1]hept-5-en-3-one

(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride
130931-85-0

(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Sonication
2: water; lipase B from Candida antarctica; benzylamine / isopropyl alcohol / 0.5 h / 60 °C / Enzymatic reaction
3: hydrogenchloride; water / 5 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1: Sonication
2: water; lipase B from Candida antarctica; benzylamine / isopropyl alcohol / 2 h / 60 °C / Enzymatic reaction
3: hydrogenchloride; water / 5 h / Reflux
View Scheme
(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride
130931-85-0

(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride

4-((4-phenyl-5-trifluoromethyl-2-thienyl)methoxy)benzaldehyde
569685-43-4

4-((4-phenyl-5-trifluoromethyl-2-thienyl)methoxy)benzaldehyde

(1R,4S)-4-(4-((4-phenyl-5-(trifluoromethyl)thiophene-2-yl)methoxy)benzylamino)cyclopentan-2-encarboxylic acid
1008769-14-9

(1R,4S)-4-(4-((4-phenyl-5-(trifluoromethyl)thiophene-2-yl)methoxy)benzylamino)cyclopentan-2-encarboxylic acid

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 6h;
(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride
130931-85-0

(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride

(+)-methyl (1R,2S,4R,5S)-2-(tert-butoxycarbonylamino)bicyclo[3.1.0]hexane-4-carboxylate

(+)-methyl (1R,2S,4R,5S)-2-(tert-butoxycarbonylamino)bicyclo[3.1.0]hexane-4-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: acetyl chloride / 16 h / 80 °C
2.1: triethylamine / dichloromethane / 3 h / 20 °C
3.1: diethylzinc / dichloromethane; hexane / 0.25 h / 0 °C
3.2: 16 h / 0 - 20 °C
View Scheme
(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride
130931-85-0

(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride

(1R,4S)-N-tert-butoxycarbonyl-4-aminocyclopent-2-ene-1-carboxylic acid methyl ester
251326-99-5

(1R,4S)-N-tert-butoxycarbonyl-4-aminocyclopent-2-ene-1-carboxylic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetyl chloride / 16 h / 80 °C
2: triethylamine / dichloromethane / 3 h / 20 °C
View Scheme
(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride
130931-85-0

(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride

(1S,4S)-N-tert-butoxycarbonyl-4-aminocyclopent-2-ene-1-carboxylic acid methyl ester

(1S,4S)-N-tert-butoxycarbonyl-4-aminocyclopent-2-ene-1-carboxylic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: acetyl chloride / 16 h / 80 °C
2: triethylamine / dichloromethane / 3 h / 20 °C
3: sodium methylate / methanol / 1 h / -10 °C
View Scheme
(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride
130931-85-0

(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride

methyl (1R,2S,4S,5S)-2-(tert-butoxycarbonylamino)bicyclo[3.1.0]hexane-4-carboxylate

methyl (1R,2S,4S,5S)-2-(tert-butoxycarbonylamino)bicyclo[3.1.0]hexane-4-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: acetyl chloride / 16 h / 80 °C
2.1: triethylamine / dichloromethane / 3 h / 20 °C
3.1: sodium methylate / methanol / 1 h / -10 °C
4.1: diethylzinc / dichloromethane; hexane / 0.25 h / 0 °C
4.2: 2 h / 0 - 20 °C
View Scheme
(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride
130931-85-0

(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride

(+)-(1R,2S,4R,5S)-2-[[5-fluoro-2-(5-fluoro-1H-pyrazolo[3,4-b]pyridin-3yl)pyrimidin-4-yl]amino]bicyclo[3.1.0]hexane-4-carboxylic acid

(+)-(1R,2S,4R,5S)-2-[[5-fluoro-2-(5-fluoro-1H-pyrazolo[3,4-b]pyridin-3yl)pyrimidin-4-yl]amino]bicyclo[3.1.0]hexane-4-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: acetyl chloride / 16 h / 80 °C
2.1: triethylamine / dichloromethane / 3 h / 20 °C
3.1: diethylzinc / dichloromethane; hexane / 0.25 h / 0 °C
3.2: 16 h / 0 - 20 °C
4.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 16 h / 60 °C
6.1: bis(pinacol)diborane; potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 0.5 h / 100 °C / Microwave irradiation
6.2: 1 h / 130 °C / Microwave irradiation
7.1: lithium hydroxide monohydrate / water; tetrahydrofuran / 2 h / 20 °C
8.1: trifluoroacetic acid / dichloromethane / 5 h / 20 °C
View Scheme
(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride
130931-85-0

(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride

(1R,2S,4S,5S)-2-[[5-fluoro-2-(5-fluoro-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidin-4-yl]amino]bicyclo[3.1.0]hexane-4-carboxylic acid

(1R,2S,4S,5S)-2-[[5-fluoro-2-(5-fluoro-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidin-4-yl]amino]bicyclo[3.1.0]hexane-4-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: acetyl chloride / 16 h / 80 °C
2.1: triethylamine / dichloromethane / 3 h / 20 °C
3.1: sodium methylate / methanol / 1 h / -10 °C
4.1: diethylzinc / dichloromethane; hexane / 0.25 h / 0 °C
4.2: 2 h / 0 - 20 °C
5.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
6.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 16 h / 60 °C
7.1: bis(pinacol)diborane; potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 0.5 h / 100 °C / Microwave irradiation
7.2: 1 h / 130 °C / Microwave irradiation
8.1: lithium hydroxide monohydrate / water; tetrahydrofuran / 2 h / 20 °C
9.1: trifluoroacetic acid / dichloromethane / 16 h / 20 °C
View Scheme
(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride
130931-85-0

(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride

(+)-methyl (1R,2S,4R,5S)-2-aminobicyclo[3.1.0]hexane-4-carboxylate

(+)-methyl (1R,2S,4R,5S)-2-aminobicyclo[3.1.0]hexane-4-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: acetyl chloride / 16 h / 80 °C
2.1: triethylamine / dichloromethane / 3 h / 20 °C
3.1: diethylzinc / dichloromethane; hexane / 0.25 h / 0 °C
3.2: 16 h / 0 - 20 °C
4.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
View Scheme
(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride
130931-85-0

(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride

(+)-methyl (1R,2S,4R,5S)-2-[(2-chloro-5-fluoropyrimidin-4-yl)amino]bicyclo[3.1.0]hexane-4-carboxylate

(+)-methyl (1R,2S,4R,5S)-2-[(2-chloro-5-fluoropyrimidin-4-yl)amino]bicyclo[3.1.0]hexane-4-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: acetyl chloride / 16 h / 80 °C
2.1: triethylamine / dichloromethane / 3 h / 20 °C
3.1: diethylzinc / dichloromethane; hexane / 0.25 h / 0 °C
3.2: 16 h / 0 - 20 °C
4.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 16 h / 60 °C
View Scheme
(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride
130931-85-0

(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride

(+)-methyl (1R,2S,4R,5S)-2-[[5-fluoro-2-(5-fluoro-1-tetrahydropyran-2-yl-pyrazolo[3,4-b]pyridin-3-yl)pyrimidin-4-yl]amino]bicyclo[3.1.0]hexane-4-carboxylate

(+)-methyl (1R,2S,4R,5S)-2-[[5-fluoro-2-(5-fluoro-1-tetrahydropyran-2-yl-pyrazolo[3,4-b]pyridin-3-yl)pyrimidin-4-yl]amino]bicyclo[3.1.0]hexane-4-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: acetyl chloride / 16 h / 80 °C
2.1: triethylamine / dichloromethane / 3 h / 20 °C
3.1: diethylzinc / dichloromethane; hexane / 0.25 h / 0 °C
3.2: 16 h / 0 - 20 °C
4.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 16 h / 60 °C
6.1: bis(pinacol)diborane; potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 0.5 h / 100 °C / Microwave irradiation
6.2: 1 h / 130 °C / Microwave irradiation
View Scheme
(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride
130931-85-0

(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride

(+)-(1R,2S,4R,5S)-2-({5-fluoro-2-[5-fluoro-1-(tetrahydropyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-4-yl}amino)bicyclo[3.1.0]hexane-4-carboxylic acid

(+)-(1R,2S,4R,5S)-2-({5-fluoro-2-[5-fluoro-1-(tetrahydropyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-4-yl}amino)bicyclo[3.1.0]hexane-4-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: acetyl chloride / 16 h / 80 °C
2.1: triethylamine / dichloromethane / 3 h / 20 °C
3.1: diethylzinc / dichloromethane; hexane / 0.25 h / 0 °C
3.2: 16 h / 0 - 20 °C
4.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 16 h / 60 °C
6.1: bis(pinacol)diborane; potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 0.5 h / 100 °C / Microwave irradiation
6.2: 1 h / 130 °C / Microwave irradiation
7.1: lithium hydroxide monohydrate / water; tetrahydrofuran / 2 h / 20 °C
View Scheme
(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride
130931-85-0

(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride

methyl (1R,2S,4S,5S)-2-aminobicyclo[3.1.0]hexane-4-carboxylate

methyl (1R,2S,4S,5S)-2-aminobicyclo[3.1.0]hexane-4-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: acetyl chloride / 16 h / 80 °C
2.1: triethylamine / dichloromethane / 3 h / 20 °C
3.1: sodium methylate / methanol / 1 h / -10 °C
4.1: diethylzinc / dichloromethane; hexane / 0.25 h / 0 °C
4.2: 2 h / 0 - 20 °C
5.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
View Scheme
(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride
130931-85-0

(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: acetyl chloride / 16 h / 80 °C
2.1: triethylamine / dichloromethane / 3 h / 20 °C
3.1: sodium methylate / methanol / 1 h / -10 °C
4.1: diethylzinc / dichloromethane; hexane / 0.25 h / 0 °C
4.2: 2 h / 0 - 20 °C
5.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
6.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 16 h / 60 °C
View Scheme

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: acetyl chloride / 16 h / 80 °C
2.1: triethylamine / dichloromethane / 3 h / 20 °C
3.1: sodium methylate / methanol / 1 h / -10 °C
4.1: diethylzinc / dichloromethane; hexane / 0.25 h / 0 °C
4.2: 2 h / 0 - 20 °C
5.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
6.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 16 h / 60 °C
7.1: bis(pinacol)diborane; potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 0.5 h / 100 °C / Microwave irradiation
7.2: 1 h / 130 °C / Microwave irradiation
View Scheme

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: acetyl chloride / 16 h / 80 °C
2.1: triethylamine / dichloromethane / 3 h / 20 °C
3.1: sodium methylate / methanol / 1 h / -10 °C
4.1: diethylzinc / dichloromethane; hexane / 0.25 h / 0 °C
4.2: 2 h / 0 - 20 °C
5.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
6.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 16 h / 60 °C
7.1: bis(pinacol)diborane; potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 0.5 h / 100 °C / Microwave irradiation
7.2: 1 h / 130 °C / Microwave irradiation
8.1: lithium hydroxide monohydrate / water; tetrahydrofuran / 2 h / 20 °C
View Scheme
methanol

methanol

(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride
130931-85-0

(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride

(+)-methyl (1R,4S)-4-aminocyclopent-2-ene-1-carboxylate hydrochloride

(+)-methyl (1R,4S)-4-aminocyclopent-2-ene-1-carboxylate hydrochloride

Conditions
ConditionsYield
With acetyl chloride at 80℃; for 16h;

(1R,4S)-4-Amino-cyclopent-2-enecarboxylic acid hydrochloride Specification

The (1R,4S)-4-Amino-cyclopent-2-enecarboxylic acid hydrochloride has CAS registry number 130931-85-0. Its molecular formula is C6H10ClNO2 and molecular weight is 163.6021. What's more, its systematic name is 4-Aminocyclopent-2-ene-1-carboxylic acid hydrochloride (1:1).

Physical properties about the (1R,4S)-4-Amino-cyclopent-2-enecarboxylic acid hydrochloride are: (1)ACD/LogP: -0.92; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 3; (4)#H bond donors: 3; (5)#Freely Rotating Bonds: 2; (6)Polar Surface Area: 29.54 Å2; (7)Flash Point: 115 °C; (8)Enthalpy of Vaporization: 55.54 kJ/mol; (9)Boiling Point: 266.6 °C at 760 mmHg; (10)Vapour Pressure: 0.00247 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C(O)C1\C=C/C(N)C1.Cl
(2) InChI: InChI=1/C6H9NO2.ClH/c7-5-2-1-4(3-5)6(8)9;/h1-2,4-5H,3,7H2,(H,8,9);1H
(3) InChIKey: JYDJHYGBXSCMJL-UHFFFAOYAR

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