3-Cyclohexylpropiolic acid

Base Information

• Chemical Name: 3-Cyclohexylpropiolic acid
• CAS No.: 4361-27-7
• Molecular Formula: C9H12O2
• Molecular Weight: 152.193
• European Community (EC) Number: 810-085-3
• DSSTox Substance ID: DTXSID00463994
• Nikkaji Number: J1.577.979I
• Wikidata: Q82289145
• Mol file: 4361-27-7.mol

Synonyms:3-Cyclohexylpropiolic acid;4361-27-7;3-cyclohexylprop-2-ynoic Acid;3-Cyclohexylpropiolicacid;Hexahydrophenylpropiolsaure;SCHEMBL420248;DTXSID00463994;MFCD20347444;AKOS013858612;AS-50127;CS-0217593;EN300-787393;O10996

Chemical Property of 3-Cyclohexylpropiolic acid

Chemical Property:

• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 152.083729621
• Heavy Atom Count: 11
• Complexity: 200

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(CC1)C#CC(=O)O

Technology Process of 3-Cyclohexylpropiolic acid

There total 10 articles about 3-Cyclohexylpropiolic 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: 98.0%

2-cyclohexylacetylene (931-48-6) + carbon dioxide (124-38-9,18923-20-1) → cyclohexylpropiolic acid (4361-27-7)

Guidance literature:

2-cyclohexylacetylene; With n-butyllithium; In diethyl ether; hexane; at -78 ℃; for 1h;

carbon dioxide; In hexane; dichloromethane; at -78 - 20 ℃;

DOI:10.1021/ja068818t

Reference yield: 93.0%

3-cyclohexyl-2-propyn-1-ol (42134-54-3) → cyclohexylpropiolic acid (4361-27-7)

Guidance literature:

3-cyclohexyl-2-propyn-1-ol; With Oxone; sodium ortho-iodobenzenesulfonate; In acetonitrile; at 70 ℃; for 1h;

With water; In acetonitrile; for 7h;

Reference yield: 92.0%

→ cyclohexylpropiolic acid (4361-27-7)

Guidance literature:

With diethoxymethylane; potassium tert-butylate; at 40 ℃; for 2h; Glovebox; Schlenk technique; Green chemistry;

upstream raw materials:

2-cyclohexylacetylene

cyclohexyl-propynoic acid ethyl ester

carbon dioxide

cyclohexanylcarbonyl chloride

Downstream raw materials:

C₂₁H₂₅N₅O₂

TH₀₄₃₀₃-040

TH₀₄₃₀₃-013

cyclohexylpropynoic acid N-hydroxy-anilide

Refernces

• 1、 Verma, Astha,Grams, R. Justin,Rastatter, Brett P.,Santos, Webster L.. "Semireduction of alkynoic acids via a transition metal-free α borylation-protodeborylation sequence". . p. 2113 - 2117. Retrieved 2019/02/25.
• 2、 Yu, Bo,Yang, Peng,Gao, Xiang,Yang, Zhenzhen,Zhao, Yanfei,Zhang, Hongye,Liu, Zhimin. "Sequential protocol for C(sp)–H carboxylation with CO2: KOtBu-catalyzed C(sp)–H silylation and KOtBu-mediated carboxylation". . p. 449 - 456. Retrieved 2018/02/06.