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

Base Information

• Chemical Name: (1S,4R)-4-Aminocyclopent-2-enecarboxylic acid
• CAS No.: 102579-72-6
• Molecular Formula: C₆H₉NO₂
• Molecular Weight: 127.143
• European Community (EC) Number: 801-728-9
• DSSTox Substance ID: DTXSID80907765
• Nikkaji Number: J1.216.923J
• ChEMBL ID: CHEMBL145625
• Mol file: 102579-72-6.mol

Synonyms:(1S,4R)-4-Aminocyclopent-2-enecarboxylic acid;134234-04-1;168471-40-7;(1S,4R)-4-aminocyclopent-2-ene-1-carboxylic acid;(-)-(1S,4R)-4-Aminocyclopent-2-enecarboxylic acid;CHEMBL145625;(1S,4R)-4-Amino-2-cyclopenten-1-carboxylic Acid Hydrochloride;(1S,4R)-4-AMINO-2-CYCLOPENTENE-1-CARBOXYLIC ACID;102579-72-6;CIS-4-AMINOCYCLOPENT-2-ENECARBOXYLIC ACID;SCHEMBL607627;2-Cyclopentene-1-carboxylicacid,4-amino-,(1S,4R)-(9CI);DTXSID80907765;VTCHZFWYUPZZKL-UHNVWZDZSA-N;BDBM50082746;MFCD00211286;AKOS015995250;AC-7956;AM84581;DS-6084;CS-0157300;(1S,4R)-4-Aminocyclopent-2-enecarboxylicacid;EN300-259931;(1S,4R)-4-Aminocyclopentene-2-carboxylic acid;3beta-Amino-4-cyclopentene-1beta-carboxylic acid;(1S,4R)-4-Amino-cyclopent-2-enecarboxylic acid;A887941;(+/-)-cis-4-aminocyclopent-2-en-1-carboxylic acid;J-500473;cis(1S,4R)-4-amino-2-cyclopentene-1-carboxylic acid;2-Cyclopentene-1-carboxylicacid,4-amino-,(1R,4R)-rel-;(-)-(1s,4R)-4-aminocyclopent-2-enecarboxylic acid, AldrichCPR

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

Chemical Property:

• Melting Point: 139.3°C
• Refractive Index: 1.4645 (estimate)
• Boiling Point: 235.91°C (rough estimate)
• PSA: 63.32000
• Density: 1.1931 (rough estimate)
• LogP: 0.67470
• 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:

98%min ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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

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

There total 25 articles about (1S,4R)-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: 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: 49.0%

racemic N-hydroxymethyl vince lactam → (-)-(1S, 4R)-4-amino-2-cyclopentene-1-carboxylic acid (102579-71-5,102579-72-6,102679-78-7,134003-04-6,134234-04-1) + (1S,4R)-N-hydroxymethyl-2-azabicyclo<2.2.1>hept-5-en-3-one (157810-20-3)

Guidance literature:

With water; benzylamine; lipase B from Candida antarctica; In isopropyl alcohol; at 60 ℃; for 2h; Enzymatic reaction;

DOI:10.1016/j.tetasy.2016.06.019

Reference yield: 46.0%

racemic 2-azabicyclo[2.2.1]hept-5-en-3-one (49805-30-3) → (1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one (130931-83-8) + (-)-(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 lipase B from Candida antarctica; In water; isopropyl alcohol; at 60 ℃; for 4h; stereospecific reaction; Enzymatic reaction;

DOI:10.1002/ejoc.200800723

upstream raw materials:

3-tosyl-2-azabicyclo [2.2.1]hepta-2,5-diene

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

cyclopenta-1,3-diene

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

Downstream raw materials:

(1S,4R)-4-(benzyloxycarbonylamino)-2-cyclopentene-1-carboxylic acid methyl ester

(1S,4R)-4-(benzyloxycarbonylamino)-2-cyclopentene-1-methanol

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

(1S,4R)-4-Benzoylamino-cyclopent-2-enecarboxylic acid methyl ester

Refernces

• 1、 Nonn, Melinda,Binder, Adrienn,Volk, Balázs,Kiss, Loránd. "Stereo- and regiocontrolled synthesis of highly functionalized cyclopentanes with multiple chiral centers". . p. 1199 - 1209. Retrieved 2020/03/17.
• 2、 Devamani, Titu,Rauwerdink, Alissa M.,Lunzer, Mark,Jones, Bryan J.,Mooney, Joanna L.,Tan, Maxilmilien Alaric O.,Zhang, Zhi-Jun,Xu, Jian-He,Dean, Antony M.,Kazlauskas, Romas J.. "Catalytic Promiscuity of Ancestral Esterases and Hydroxynitrile Lyases". supporting information. p. 1046 - 1056. Retrieved 2016/02/05.