(1R,4S)-4-Aminocyclopent-2-enecarboxylic acid

Base Information

• Chemical Name: (1R,4S)-4-Aminocyclopent-2-enecarboxylic acid
• CAS No.: 134003-04-6
• Molecular Formula: C6H9NO2
• Molecular Weight: 127.143
• Hs Code.: 29299000
• European Community (EC) Number: 801-728-9
• DSSTox Substance ID: DTXSID701236833
• Nikkaji Number: J1.216.924H
• ChEMBL ID: CHEMBL344794
• Mol file: 134003-04-6.mol

Synonyms:134003-04-6;(1R,4S)-4-AMINOCYCLOPENT-2-ENECARBOXYLIC ACID;(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid;(1R,4S)-rel-4-Aminocyclopent-2-enecarboxylic acid;(+)-(1R,4S)-4-Aminocyclopent-2-enecarboxylic acid;168471-40-7;CHEMBL344794;MFCD00211285;2-Cyclopentene-1-carboxylic acid, 4-amino-, (1R,4S)-;(1r,4s)-4-amino-2-cyclopentene-1-carboxylic acid;CIS-4-AMINOCYCLOPENT-2-ENECARBOXYLIC ACID;(1R,4S)-4-amino-cyclopent-2-ene carboxylic acid;SCHEMBL607058;VTCHZFWYUPZZKL-CRCLSJGQSA-N;DTXSID701236833;BDBM50082743;MFCD27922565;AKOS006340572;AKOS015854146;AC-7955;PS-12183;(+)-cis-3-amino-4-cyclopentenecarboxylic acid;EN300-1703497;(1R,4S)-4-Amino-cyclopent-2-enecarboxylic acid;(1R,4S)-rel-4-Aminocyclopent-2-enecarboxylicacid;3alpha-Amino-4-cyclopentene-1alpha-carboxylic acid;A806713;(1R,4S)-4-amino-2-cyclopenten-1-carboxylic acid;(1R,4S)-4-azaniumylcyclopent-2-ene-1-carboxylate;J-500359;2-Cyclopentene-1-carboxylic acid, 4-amino-, (1R,4S)-rel-;(+)-(1R,4S)-4-aminocyclopent-2-enecarboxylic acid, AldrichCPR

Chemical Property of (1R,4S)-4-Aminocyclopent-2-enecarboxylic acid

Chemical Property:

• Appearance/Colour: brownish crystalline powder or flakes
• Vapor Pressure: 0.002mmHg at 25°C
• Melting Point: 180 °C
• Refractive Index: 1.548
• Boiling Point: 266.55 °C at 760 mmHg
• PKA: 3.52±0.20(Predicted)
• Flash Point: 115.006 °C
• PSA: 63.32000
• Density: 1.249 g/cm³
• LogP: 0.67470
• Storage Temp.: Inert atmosphere,Room Temperature
• Sensitive.: Air Sensitive
• XLogP3: -2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 127.063328530
• Heavy Atom Count: 9
• Complexity: 153

Purity/Quality:

99% ^*data from raw suppliers

(1R,4S)-4-Aminocyclopent-2-enecarboxylicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 36/37/38-20/21/22-43-22
• Safety Statements: 36/37/39-26-22-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C=CC1N)C(=O)O
• Isomeric SMILES: C1[C@H](C=C[C@H]1N)C(=O)O
• Uses: (1R,4S)-(+)-4-Aminocyclopent-2-enecarboxylic acid is used as organic chemical synthesis intermediate.

Technology Process of (1R,4S)-4-Aminocyclopent-2-enecarboxylic acid

There total 34 articles about (1R,4S)-4-Aminocyclopent-2-enecarboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.4%

(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid methyl ester tartrate (419563-23-8,419563-22-7) → (1R,4S)-4-aminocyclopenten-2-ene-1-carboxylic acid (134003-04-6)

Guidance literature:

With methanol; water; triethylamine; lithium hydroxide; at -20 ℃; pH=6 - 7;

Reference yield: 83.7%

(1S,4R)-4-aminocyclopent-2-ene-1-carboxylic acid methyl ester tartrate (419563-22-7) → (-)-(1S, 4R)-4-amino-2-cyclopentene-1-carboxylic acid (102579-71-5,102579-72-6,102679-78-7,134003-04-6,134234-04-1)

Guidance literature:

With methanol; water; triethylamine; lithium hydroxide; at -20 ℃; pH=6 - 7;

Reference yield: 49.9%

racemic 2-azabicyclo[2.2.1]hept-5-en-3-one (49805-30-3) → (-)-2-azabicyclo[2.2.1]hept-5-en-3-one (79200-56-9) + (1R,4S)-4-aminocyclopenten-2-ene-1-carboxylic acid (134003-04-6)

Guidance literature:

With (+)-γ-lactamase from Bradyrhizobium japonicum USDA 6; In aq. buffer; at 45 ℃; for 1h; pH=8; Temperature; pH-value; enantioselective reaction; Catalytic behavior; Resolution of racemate; Enzymatic reaction;

DOI:10.1016/j.bmcl.2015.07.054

upstream raw materials:

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

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

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

(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid methyl ester tartrate

Downstream raw materials:

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

(-)-2-azabicyclo[2.2.1]hept-5-en-3-one

benzyl (1S,3R)-3-amino-1-isopropylcyclopentanecarboxylate hydrochloride

C₂₁H₃₁NO₄

Refernces

• 1、 Smith, Mark E.B.,Lloyd, Michael C.,Derrien, Nadine,Lloyd, Richard C.,Taylor, Stephen J.C.,Chaplin, David A.,Casy, Guy,McCague, Raymond. "An efficient route to all eight stereoisomers of a tri-functionalised cyclopentane scaffold for drug discovery". . p. 703 - 705. Retrieved 2001.
• 2、 -. "Chemical preparation method of 2-azabicyclo [2.2.1] hept-5-ene-3-one with optical activity". . . Retrieved 2020/05/08.
• 3、 Li, Hongxia,Zhu, Shaozhou,Zheng, Guojun. "Promiscuous (+)-γ-lactamase activity of an amidase from nitrile hydratase pathway for efficient synthesis of carbocyclic nucleosides intermediate". supporting information. p. 1071 - 1076. Retrieved 2018/03/01.