(1R,2S,5S)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid

Base Information

• Chemical Name: (1R,2S,5S)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid
• CAS No.: 33294-81-4
• Molecular Formula: C6H9NO2
• Molecular Weight: 127.14
• Hs Code.: 2933990090
• European Community (EC) Number: 624-403-1
• DSSTox Substance ID: DTXSID90454134
• Nikkaji Number: J83.167K
• Wikidata: Q72444210
• Metabolomics Workbench ID: 123287
• ChEMBL ID: CHEMBL1311694
• Mol file: 33294-81-4.mol

Synonyms:(1R,2S,5S)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid;33294-81-4;74984-02-4;CHEMBL1311694;(1R,2S,5S)-REL-3-AZABICYCLO[3.1.0]HEXANE-2-CARBOXYLIC ACID;(1R,2S,5S)-Rel-3-Azabicyclo-[3.1.0]hexane-2-carboxylic acid;cis-3-Azabicyclo[3.1.0]hexane-2-carboxylic acid;cis-3,4-methano-l-proline;MLS000736076;SCHEMBL422735;DTXSID90454134;HMS2643D11;22255-16-9;BDBM50357218;MFCD05663832;AKOS006238147;SS-4355;SMR000338626;CS-0029924;P10238;(1R,2S,5S)-Rel-3-Azabicyclo-[3.1.0]hexane-2-carboxylicacid;(2S)-3alpha,4alpha-Methanopyrrolidine-2alpha-carboxylic acid;(1R,2S,5S)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid >99%ee

Chemical Property of (1R,2S,5S)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid

Chemical Property:

• Melting Point: 224-230 °C(Solv: water (7732-18-5); acetone (67-64-1))
• Boiling Point: 280℃
• PKA: 2.38±0.20(Predicted)
• Flash Point: 123℃
• PSA: 49.33000
• Density: 1.327
• LogP: 0.00770
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: -2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 127.063328530
• Heavy Atom Count: 9
• Complexity: 157

Purity/Quality:

99.0% ^*data from raw suppliers

(1R,2S,5S)-3-Azabicyclo[3.1.0]hexane-2-carboxylic acid 99.0 (ee)% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2C1C(NC2)C(=O)O
• Isomeric SMILES: C1[C@H]2[C@@H]1[C@H](NC2)C(=O)O

Technology Process of (1R,2S,5S)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid

There total 13 articles about (1R,2S,5S)-3-azabicyclo[3.1.0]hexane-2-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: 79.0%

(1R,2S,5S)-N-trifluoroacetyl-3-azabicyclo[3.1.0]hexane-2-carboxylic acid (198015-86-0) → (1R,2S,5S)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid (33294-81-4)

Guidance literature:

With potassium hydroxide; In methanol; for 2h;

DOI:10.1016/S0040-4020(97)00988-5

Reference yield: 70.0%

(1R,2S,5S)-3-tert-butoxycarbonyl-2-methoxycarbonyl-3-azabicyclo[3.1.0]hexane (865184-03-8) → (1R,2S,5S)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid (33294-81-4)

Guidance literature:

With hydrogenchloride; for 3h; Heating;

DOI:10.1016/j.tet.2005.06.051

Reference yield:

→ (1R,5S)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid (22255-16-9,27762-08-9,33294-81-4,72029-78-8,72496-47-0,73804-70-3,74984-02-4)

Guidance literature:

V, Ionenaustauschchromatographie;

DOI:10.1021/ja00743a030

upstream raw materials:

(1R,2S,5S)-N-trifluoroacetyl-3-azabicyclo[3.1.0]hexane-2-carboxylic acid

(1R,2S,5S)-3-tert-butoxycarbonyl-2-methoxycarbonyl-3-azabicyclo[3.1.0]hexane

(1R,2S,5S)-4-Oxo-3-aza-bicyclo[3.1.0]hexane-2-carboxylic acid methyl ester

(1S,4S,5R)-3-tert-butoxycarbonyl-4-methoxycarbonyl-3-azabicyclo[3.1.0]hexan-2-one

Downstream raw materials:

(1R,2S,5S)-3-azabicyclo[3.1.0]hexan-2-ylmethanol

(-)-cis-(1R,2S,5S)-3-(tert-butoxycarbonyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid