[trans-4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-cyclohexyl]-acetic acid

Base Information

• Chemical Name: [trans-4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-cyclohexyl]-acetic acid
• CAS No.: 76308-29-7
• Molecular Formula: C₁₆H₁₇NO₄
• Molecular Weight: 287.315
• DSSTox Substance ID: DTXSID401153440
• Mol file: 76308-29-7.mol

Synonyms:Oprea1_420624;SCHEMBL2053503;SCHEMBL12544749;ZVRQAVXLPKCSNL-XYPYZODXSA-N;DTXSID401153440;AKOS024366856;[trans-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-cyclohexyl]-acetic acid;trans-4-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)cyclohexaneacetic acid;76308-29-7

Chemical Property of [trans-4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-cyclohexyl]-acetic acid

Chemical Property:

• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 287.11575802
• Heavy Atom Count: 21
• Complexity: 429

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CC(CCC1CC(=O)O)N2C(=O)C3=CC=CC=C3C2=O

Technology Process of [trans-4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-cyclohexyl]-acetic acid

There total 4 articles about [trans-4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-cyclohexyl]-acetic 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: 95.0%

phthalic anhydride (85-44-9) + trans-4-aminocyclohexylacetic acid hydrochloride (76325-96-7,109572-36-3) → N-phthalyl-trans-4-aminocyclohexylacetic acid (76308-29-7)

Guidance literature:

With pyridine; Heating;

DOI:10.1007/BF00951237

Reference yield: 86.0%

2-((trans)-4-((tert-butoxycarbonyl)amino)cyclohexyl)acetic acid + phthalic anhydride (85-44-9) → N-phthalyl-trans-4-aminocyclohexylacetic acid (76308-29-7)

Guidance literature:

2-((trans)-4-((tert-butoxycarbonyl)amino)cyclohexyl)acetic acid; With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 3h; Inert atmosphere;

phthalic anhydride; With pyridine; In dichloromethane; for 4h; Inert atmosphere; Reflux;

With acetic anhydride; for 3h; Inert atmosphere; Reflux;

Reference yield:

4-nitrobenzeneacetic acid (104-03-0) → N-phthalyl-trans-4-aminocyclohexylacetic acid (76308-29-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaOH, H₂, 2.) HCl (conc.) / 1.) Raney Ni / 1.) H₂O, 130 deg C, 150 atm, 8 h

2: 95 percent / pyridine / Heating

With pyridine; hydrogenchloride; sodium hydroxide; hydrogen; nickel;

DOI:10.1007/BF00951237

upstream raw materials:

phthalic anhydride

trans-4-aminocyclohexylacetic acid hydrochloride

4-nitrobenzeneacetic acid

(cis-4-amino-cyclohexyl)-acetic acid