Ethyl (1S,2S)-trans-2-hydroxycyclohexanecarboxylate

Base Information

• Chemical Name: Ethyl (1S,2S)-trans-2-hydroxycyclohexanecarboxylate
• CAS No.: 29569-79-7
• Molecular Formula: C9H16 O3
• Molecular Weight: 172.224
• Hs Code.: 2918199090
• DSSTox Substance ID: DTXSID001253511
• Nikkaji Number: J729.870F
• Mol file: 29569-79-7.mol

Synonyms:Ethyl (1S,2S)-trans-2-hydroxycyclohexanecarboxylate;29569-79-7;ethyl (1S,2S)-2-hydroxycyclohexane-1-carboxylate;Ethyl trans-2-hydroxycyclohexanecarboxylate;2-Hydroxy-cyclohexanecarboxylic acid ethyl ester, trans;ethyl trans-2-hydroxy-1-cyclohexanecarboxylate;(1S,2S)-ethyl 2-hydroxycyclohexanecarboxylate;SCHEMBL4569123;DTXSID001253511;MFCD03095441;AS-38805;ethyl (1s,2s)-2-hydroxycyclohexanecarboxylate;E87680;J-017568;2beta-Hydroxycyclohexane-1alpha-carboxylic acid ethyl ester;Cyclohexanecarboxylicacid, 2-hydroxy-, ethyl ester, (1S,2S)-

Chemical Property of Ethyl (1S,2S)-trans-2-hydroxycyclohexanecarboxylate

Chemical Property:

• Refractive Index: n20/D 1.462
• PSA: 46.53000
• LogP: 1.10060
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 172.109944368
• Heavy Atom Count: 12
• Complexity: 156

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1CCCCC1O
• Isomeric SMILES: CCOC(=O)[C@H]1CCCC[C@@H]1O

Technology Process of Ethyl (1S,2S)-trans-2-hydroxycyclohexanecarboxylate

There total 49 articles about Ethyl (1S,2S)-trans-2-hydroxycyclohexanecarboxylate 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%

ethyl 2-oxocyclohexane carboxylate (1655-07-8) → ethyl (1S,2S)-2-hydroxycyclohexanecarboxylate (29569-79-7)

Guidance literature:

In ethanol; at 25 ℃; prepared by the Colletotrichum gloeosporoides MMP 3233;

DOI:10.1016/S0040-4039(00)84603-1

Reference yield: 93.0%

ethyl (1R,2S)-2-hydroxycyclohexane-1-carboxylate (61586-78-5) → ethyl (1S,2S)-2-hydroxycyclohexanecarboxylate (29569-79-7)

Guidance literature:

With sodium; In ethanol; for 72h; Ambient temperature;

DOI:10.1002/hlca.19870700406

Reference yield: 90.2%

ethyl 2-oxocyclohexane carboxylate (1655-07-8) → ethyl (1S,2R)-2-hydroxycyclohexanecarboxylate (119068-37-0) + ethyl anti-(1R,2R)-2-hydroxycyclohexanecarboxylate (119068-36-9) + ethyl (1S,2S)-2-hydroxycyclohexanecarboxylate (29569-79-7) + ethyl (1R,2S)-2-hydroxycyclohexane-1-carboxylate (61586-78-5)

Guidance literature:

With hydrogen; (benzene)>Cl; In dichloromethane; at 50 ℃; for 80h; under 76000.1 Torr; Product distribution; other solvent: ethanol;

DOI:10.1016/S0957-4166(00)82262-4

upstream raw materials:

ethanol

Salicylic acid

ethyl 2-oxocyclohexane carboxylate

sulfuric acid

Downstream raw materials:

cis-2-aminocyclohexanecarboxylic acid amide

(+/-)-(1R,2S)-cis-2-hydroxy-1-cyclohexanecarboxylic acid

(+/-)-trans-2-hydroxy-cyclohexane-carboxylic acid-⁽¹⁾-hydrazide

2-benzyloxymethyl-2-ethoxycarbonylcyclohexanol;

Refernces

• 1、 Tsunekawa, Ryuji,Hanaya, Kengo,Higashibayashi, Shuhei,Shoji, Mitsuru,Sugai, Takeshi. "Chemoenzymatic approaches to the synthesis of the (1S,2R)-isomer of benzyl 2-hydroxycyclohexanecarboxylate". . p. 84 - 89. Retrieved 2017/12/06.
• 2、 Martnez-Prieto, Luis Miguel,Ferry, Anglique,Lara, Patricia,Richter, Christian,Philippot, Karine,Glorius, Frank,Chaudret, Bruno. "New Route to Stabilize Ruthenium Nanoparticles with Non-Isolable Chiral N-Heterocyclic Carbenes". . p. 17495 - 17502. Retrieved 2016/01/25.