(1R,2S)-2-amino-4-methylcyclopent-3-ene-1-carboxylic acid

Base Information

• Chemical Name: (1R,2S)-2-amino-4-methylcyclopent-3-ene-1-carboxylic acid
• CAS No.: 777850-76-7
• Molecular Formula: C₇H₁₁NO₂
• Molecular Weight: 141.17
• ChEMBL ID: CHEMBL1195746
• DSSTox Substance ID: DTXSID60414987
• Nikkaji Number: J1.876.297H
• Wikidata: Q82224096
• Mol file: 777850-76-7.mol

Synonyms:156292-41-0;(1R,2S)-2-amino-4-methylcyclopent-3-ene-1-carboxylic acid;3-Cyclopentene-1-carboxylicacid,2-amino-4-methyl-,cis-(9CI);AC1NQNA2;777850-76-7;CHEMBL1195746;DTXSID60414987;AKOS006364333;(1R,2S)-2-amino-4-methyl-cyclopent-3-ene-1-carboxylic acid;3-Cyclopentene-1-carboxylic acid, 2-amino-4-methyl-, (1R,2S)-;3-Cyclopentene-1-carboxylicacid,2-amino-4-methyl-,(1R,2S)-(9ci)

Chemical Property of (1R,2S)-2-amino-4-methylcyclopent-3-ene-1-carboxylic acid

Chemical Property:

• XLogP3: -2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 141.078978594
• Heavy Atom Count: 10
• Complexity: 186

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC(C(C1)C(=O)O)N
• Isomeric SMILES: CC1=C[C@@H]([C@@H](C1)C(=O)O)N

Technology Process of (1R,2S)-2-amino-4-methylcyclopent-3-ene-1-carboxylic acid

There total 8 articles about (1R,2S)-2-amino-4-methylcyclopent-3-ene-1-carboxylic 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:

(-)-(1R,2S)-2-amino-4-methylenecyclopentanecarboxylic acid (198022-65-0,156292-16-9,156292-48-7,755750-29-9,526194-96-7,786615-32-5) → (-)-(1R,5S)-5-amino-3-methyl-cyclopent-2-enecarboxylic acid (156292-40-9) + (+)-(1R,2S)-2-amino-4-methyl-cyclopent-3-enecarboxylic acid (777850-76-7)

Guidance literature:

With chloro-trimethyl-silane; sodium iodide; In acetonitrile; at 75 ℃; Title compound not separated from byproducts;

DOI:10.1016/j.tetasy.2007.02.019

Reference yield:

(1R,2S)-2-tert-Butoxycarbonylamino-4-methylene-cyclopentanecarboxylic acid → (-)-(1R,5S)-5-amino-3-methyl-cyclopent-2-enecarboxylic acid (156292-40-9) + (+)-(1R,2S)-2-amino-4-methyl-cyclopent-3-enecarboxylic acid (777850-76-7)

Guidance literature:

(1R,2S)-2-tert-Butoxycarbonylamino-4-methylene-cyclopentanecarboxylic acid; With chloro-trimethyl-silane; sodium iodide; In acetonitrile;

With N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide; sodium carbonate; In 1,4-dioxane;

With piperidine;

DOI:10.1016/S0960-894X(02)00958-7

Reference yield:

(-)-(1R,2R)-4-methyl-2-(3-phenyl-allyloxycarbonylamino)-cyclopent-4-enecarboxylic acid 3-phenyl-allyl ester (939962-90-0) → (-)-(1R,2R)-2-amino-4-methyl-cyclopent-3-enecarboxylic acid (777850-76-7)

Guidance literature:

With morpholine; triphenylphosphine; palladium diacetate; In ethanol; for 2h; Heating;

DOI:10.1016/j.tetasy.2007.02.019

upstream raw materials:

(-)-(1R,2S)-2-amino-4-methylenecyclopentanecarboxylic acid

(-)-(1R,2R)-4-methyl-2-(3-phenyl-allyloxycarbonylamino)-cyclopent-4-enecarboxylic acid 3-phenyl-allyl ester

5-methylenetetrahydrocyclopenta[c]furan-1,3-dione