2-(2-oxocyclohexyl)acetic Acid

Base Information

• Chemical Name: 2-(2-oxocyclohexyl)acetic Acid
• CAS No.: 1438-96-6
• Molecular Formula: C8H12O3
• Molecular Weight: 156.181
• Hs Code.: 2918300090
• DSSTox Substance ID: DTXSID10448313
• Nikkaji Number: J611.414H
• Mol file: 1438-96-6.mol

Synonyms:2-(2-oxocyclohexyl)acetic Acid;1438-96-6;Cyclohexaneacetic acid, 2-oxo-;2-Oxocyclohexylacetic acid;2-Oxocyclohexaneacetic acid;2-(2-oxocyclohexyl)aceticacid;SCHEMBL2764882;(2-oxocyclohex-1-yl)acetic acid;DTXSID10448313;QRUYAODUCVMGQQ-UHFFFAOYSA-N;BAA43896;MFCD20638190;AKOS022635470;CS-0446477;A902777;F2147-4269

Chemical Property of 2-(2-oxocyclohexyl)acetic Acid

Chemical Property:

• Melting Point: 72.6-74 °C
• Boiling Point: 163 °C
• PKA: 4.33±0.10(Predicted)
• PSA: 54.37000
• Density: 1.155±0.06 g/cm3(Predicted)
• LogP: 1.22040
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 156.078644241
• Heavy Atom Count: 11
• Complexity: 174

Purity/Quality:

95% ^*data from raw suppliers

2-(2-Oxocyclohexyl)acetic acid 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(=O)C(C1)CC(=O)O
• Uses: 2-(2-Oxocyclohexyl)acetic acid is used as a reactant in the preparation of β-carbolines via diastereo- and enantioselective Bronsted acid catalyzed N-acyliminium cyclization cascades of tryptamines and keto acids/esters.

Technology Process of 2-(2-oxocyclohexyl)acetic Acid

There total 33 articles about 2-(2-oxocyclohexyl)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: 100.0%

ethyl 2-(2-oxocyclohexyl)acetate (24731-17-7) → (2-oxocyclohexyl)acetic acid (1438-96-6)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 20h;

DOI:10.1021/jo0205661

Reference yield: 83.0%

bromoacetic acid methyl ester (96-32-2) + ethyl 2-oxocyclohexane carboxylate (1655-07-8) → (2-oxocyclohexyl)acetic acid (1438-96-6)

Guidance literature:

bromoacetic acid methyl ester; ethyl 2-oxocyclohexane carboxylate; With potassium carbonate; In acetone; Inert atmosphere; Reflux;

With hydrogenchloride; In water; for 5h; Inert atmosphere; Reflux;

DOI:10.1021/acs.orglett.7b01963

Reference yield: 75.0%

2-allylcyclohexan-1-one (94-66-6) → (2-oxocyclohexyl)acetic acid (1438-96-6)

Guidance literature:

With potassium permanganate; sodium periodate; In water; acetone; at 20 ℃;

DOI:10.1002/adsc.200800691

upstream raw materials:

ethyl 2-(2-oxocyclohexyl)acetate

(1-ethoxycarbonyl-2-oxo-cyclohexyl)-acetic acid ethyl ester

trans-(2-hydroxy-cyclohexyl)acetic acid

cyclohexanone

Downstream raw materials:

ethyl 2-(2-oxocyclohexyl)acetate

1-phenyl-1,3,3a,4,5,6-hexahydro-indol-2-one

(2-hydroxy-cyclohexyl)-acetic acid

N-benzyl-2-(2-oxo-cyclohexyl)acetamide

Refernces

• 1、 -. "Acyl acid derivative and preparation method and medical application thereof". Paragraph 0438-0442. . Retrieved 2020/07/02.
• 2、 Li, Zhengning,Lam, Shuk Mei,Ip, Ignatius,Wong, Wing-Tak,Chiu, Pauline. "Rearrangements of α-Diazo-β-hydroxyketones for the Synthesis of Bicyclo[m.n.1]alkanones". supporting information. p. 4464 - 4467. Retrieved 2017/09/11.