2-Aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid

Base Information

• Chemical Name: 2-Aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid
• CAS No.: 177317-28-1
• Molecular Formula: C₈H₁₁NO₄
• Molecular Weight: 185.18
• DSSTox Substance ID: DTXSID70870131
• Nikkaji Number: J2.371.140K
• Mol file: 177317-28-1.mol

Synonyms:(+)-(1S,2S,5R,6S)-2-aminobicyclo(3.1.0)hexane-2,6-dicarboxylic acid;2-aminobicyclo(3.1.0)hexane-2,6-dicarboxylic acid;eglumetad;LY 314582;LY 354740;LY 366563;LY-314582;LY-354740;LY-366563;LY314582;LY354740;LY366563

Chemical Property of 2-Aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid

Chemical Property:

• Vapor Pressure: 1.06E-06mmHg at 25°C
• Boiling Point: 376.4°Cat760mmHg
• Flash Point: 181.4°C
• PSA: 100.62000
• Density: 1.569g/cm³
• LogP: 0.20940
• Storage Temp.: room temp
• Solubility.: Aqueous Base
• XLogP3: -3.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 185.06880783
• Heavy Atom Count: 13
• Complexity: 290

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid 95%+ ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22-24/25-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(C2C1C2C(=O)O)(C(=O)O)N
• Uses: LY-354740 hydrate has been used as a metabotropic glutamate receptor group II/III agonist to study its behavioral effectsof electric shock on Gammarus fossarum.

Technology Process of 2-Aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid

There total 38 articles about 2-Aminobicyclo[3.1.0]hexane-2,6-dicarboxylic 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: 86.0%

(-)-bicyclo[3.1.0]hexane-6-carboxylate-2-spiro-5'-hydantoin → (+)-2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (176027-90-0,176199-49-8,177317-28-1,207553-80-8,597540-64-2)

Guidance literature:

With sodium hydroxide; for 28h; Heating;

DOI:10.1021/jm9606756

Reference yield: 85.0%

(1S,2S,5R,6S)-ethyl 2-spirohydantoin-bicyclo[3.1.0]hexane-6-carboxylate (188885-88-3) → eglumetad (176199-48-7,176027-90-0,176199-49-8,177317-28-1,207553-80-8,597540-64-2)

Guidance literature:

(1S,2S,5R,6S)-ethyl 2-spirohydantoin-bicyclo[3.1.0]hexane-6-carboxylate; With sodium hydroxide; for 28h; Reflux;

With hydrogenchloride; In water; at 0 - 20 ℃; for 3h; pH=3;

DOI:10.1016/j.tetasy.2010.04.051

Reference yield: 64.0%

(1S,2S,5R,6S)-2-Acetylamino-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid dimethyl ester (219762-29-5) → eglumetad (176199-48-7,176027-90-0,176199-49-8,177317-28-1,207553-80-8,597540-64-2)

Guidance literature:

With hydrogenchloride; Dowex 50WX₈-100; Heating;

DOI:10.1016/S0040-4039(98)02092-9

upstream raw materials:

cyclopent-2-enone

(+/-)-(1S,5R,6S)-ethyl 2-oxobicyclo[3.1.0]hexane-6-carboxylate

(1S,2S,5R,6S)-ethyl 2-spirohydantoin-bicyclo[3.1.0]hexane-6-carboxylate

(1S,2S,5R,6S)-2-Acetylamino-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid dimethyl ester

Refernces

• 1、 Ohfune, Yasufumi,Demura, Takashi,Iwama, Seiji,Matsuda, Hiromi,Namba, Kosuke,Shimamoto, Keiko,Shinada, Tetsuro. "Stereocontrolled synthesis of a potent agonist of group II metabotropic glutamate receptors, (+)-LY354740, and its related derivatives". . p. 5431 - 5434. Retrieved 2007/10/03.
• 2、 Dominguez, Carmen,Ezquerra, Jesus,Baker, S. Richard,Borrelly, Stephane,Prieto, Lourdes,Espada, Modesta,Pedregal, Carmen. "Enantiospecific synthesis of (1S,2S,5R,6S)-2-aminobicyclo[3.1.0]hexane- 2,6-dicarboxylic acid by a modified Corey-Link reaction". . p. 9305 - 9308. Retrieved 2007/10/03.