(1R,2R)-TRANS-1,2-CYCLOHEXANEDIOL

Base Information

• Chemical Name: (1R,2R)-TRANS-1,2-CYCLOHEXANEDIOL
• CAS No.: 1072-86-2
• Molecular Formula: C₆H₁₂O₂
• Molecular Weight: 116.16
• Hs Code.: 29061990
• Mol file: 1072-86-2.mol

Synonyms:1,2-Cyclohexanediol,(1R,2R)-(-)- (8CI);1,2-Cyclohexanediol, (1R-trans)-;trans-(R,R)-1,2-Cyclohexanediol;(1R,2R)-(-)-1,2-Cyclohexanediol;(1R,2R)-1,2-Cyclohexanediol;(1R,2R)-trans-1,2-Cyclohexanediol;(R,R)-1,2-Cyclohexanediol;(R,R)-trans-1,2-Cyclohexanediol;(-)-trans-Cyclohexane-1,2-diol;(-)-trans-(1R,2R)-1,2-Dihydroxycyclohexane;(-)-trans-1,2-Cyclohexanediol;

Chemical Property of (1R,2R)-TRANS-1,2-CYCLOHEXANEDIOL

Chemical Property:

• Appearance/Colour: white to off-white crystals
• Vapor Pressure: 0.00839mmHg at 25°C
• Melting Point: 107-109 °C
• Refractive Index: 1.526
• Boiling Point: 236.7 °C at 760 mmHg
• PKA: 14.49±0.40(Predicted)
• Flash Point: 114.3 °C
• PSA: 40.46000
• Density: 1.156 g/cm³
• LogP: 0.28220
• Storage Temp.: 2-8°C

Purity/Quality:

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

(1R,2R)-trans-1,2-Cyclohexanediol 99% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1R,2R)-TRANS-1,2-CYCLOHEXANEDIOL

There total 148 articles about (1R,2R)-TRANS-1,2-CYCLOHEXANEDIOL 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: 90.3%

cyclohexene (110-83-8) → cyclohexenone (930-68-7) + (1R,2R)-trans-1,2-cyclohexanediol (1072-86-2,1460-57-7,1792-81-0,54383-22-1,57794-08-8,931-17-9) + Cyclohex-2-enol (822-67-3)

Guidance literature:

With tungsten(VI) oxide dihydrate; phosphoric acid; dihydrogen peroxide; In water; at 70 ℃; for 3h;

DOI:10.1016/j.apcata.2013.06.023

Reference yield: 47.0%

cyclohexane-1,2-epoxide (286-20-4) → Adipic acid (124-04-9) + (1R,2R)-trans-1,2-cyclohexanediol (1072-86-2,1460-57-7,1792-81-0,54383-22-1,57794-08-8,931-17-9)

Guidance literature:

With 1-butyl-3-methylimidazolium phosphotungstate; dihydrogen peroxide; acetophenone; In water; at 60 ℃; for 24h; Reagent/catalyst;

DOI:10.3390/molecules24040783

Reference yield: 45.0%

trans-1,2-cyclohexandiol (1460-57-7) + benzaldehyde (100-52-7) → (1R,2R)-trans-1,2-cyclohexanediol (1072-86-2,1460-57-7,1792-81-0,54383-22-1,57794-08-8,931-17-9) + 2-hydroxy-2-phenylacetophenone (119-53-9,579-44-2) + benzoic acid (65-85-0,8013-63-6)

Guidance literature:

With 5a(S),10b(R)-5a,10b-dihydro-2-(pentafluorophenyl)-4H,6H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazinium tetrafluoroborate; 3-benzyl-2',3',4',5'-tetraacetylriboflavin; triethylamine; In chloroform; at 20 ℃; for 3h; optical yield given as %ee; enantioselective reaction; Resolution of racemate; Air; Molecular sieve;

DOI:10.1002/chem.201100737

upstream raw materials:

1-acetoxy-2-iodocyclohexane

1-chloro-2-iodocyclohexane

trans-1,2-cyclohexandiol

(S)-α-hydroxycyclohexanone

Downstream raw materials:

2-propyl-1-(trimethylsilyl)-9H-fluoren-9-one

(1R,2R)-trans-1,2-cyclohexanediol 1-(6-methoxy-2-naphthoate)

(R,R)-2-(p-nitrobenzoyloxy)-1-cyclohexanol

(1R,2R)-1,2-bis[2-ethoxycarbonyl-1-oxaethyl]cyclohexane

Refernces

• 1、 Liu, Tieliang,Jin, Fang,Wang, Xianqiao,Fan, Yangchun,Yuan, Ming. "Synthesis of titanium containing MCM-41 from industrial hexafluorosilicic acid as epoxidation catalyst". . p. 316 - 323. Retrieved 2017.
• 2、 Hayashi, Yujiro,Yamaguchi, Junichiro,Sumiya, Tatsunobu,Shoji, Mitsuru. "Direct proline-catalyzed asymmetric α-aminoxylation of ketones". . p. 1112 - 1115. Retrieved 2004.
• 3、 Abdellah, Ibrahim,Martini, Cyril,Dos Santos, Amandine,Dragoe, Diana,Guérineau, Vincent,Huc, Vincent,Schulz, Emmanuelle. "Calix[8]arene as New Platform for Cobalt-Salen Complexes Immobilization and Use in Hydrolytic Kinetic Resolution of Epoxides". . p. 4761 - 4767. Retrieved 2018.
• 4、 Antonetti, Claudia,Galletti, Anna Maria Raspolli,Accorinti, Pasquale,Alini, Stefano,Babini, Pierpaolo,Raabova, Katerina,Rozhko, Elena,Caldarelli, Aurora,Righi, Paolo,Cavani, Fabrizio,Concepcion, Patricia. "Two alternative routes for 1,2-cyclohexanediol synthesis by means of green processes: Cyclohexene dihydroxylation and catechol hydrogenation". . p. 21 - 31. Retrieved 2013.
• 5、 Sun, Zhoutong,Lonsdale, Richard,Li, Guangyue,Reetz, Manfred T.. "Comparing Different Strategies in Directed Evolution of Enzyme Stereoselectivity: Single- versus Double-Code Saturation Mutagenesis". . p. 1865 - 1872. Retrieved 2016.
• 6、 Li, Guangyue,Zhang, Hui,Sun, Zhoutong,Liu, Xinqi,Reetz, Manfred T.. "Multiparameter Optimization in Directed Evolution: Engineering Thermostability, Enantioselectivity, and Activity of an Epoxide Hydrolase". . p. 3679 - 3687. Retrieved 2016.
• 7、 Cagnon,Porto,Marsaioli,Manfio,Eguchi. "First evaluation of the Brazilian microorganisms biocatalytic potential". . p. 2237 - 2242. Retrieved 1999.
• 8、 Iida, Takehiko,Yamamoto, Noriyoshi,Matsunaga, Shigeki,Woo, Hee-Gweon,Shibasaki, Masakatsu. "Enantioselective ring opening of epoxides with 4-methoxyphenol catalyzed by gallium heterobimetallic complexes: An efficient method for the synthesis of optically active 1,2-diol monoethers". . p. 2223 - 2226. Retrieved 1998.
• 9、 Bortolini, Olga,Fantin, Giancarlo,Fogagnolo, Marco,Giovannini, Pier Paolo,Guerrini, Alessandra,Medici, Alessandro. "An Easy Approach to the Synthesis of Optically Active vic-Diols: A New Single-Enzyme System". . p. 1854 - 1856. Retrieved 1997.
• 10、 Bellucci, Giuseppe,Capitani, Isabella,Chiappe, Cinzia,Marioni, Franco. "Product Enantioselectivity of the Microsomal and Cytosolic Epoxide Hydrolase catalysed Hydrolysis of meso Epoxides". . p. 1170 - 1171. Retrieved 1989.