trans-2-Phenyl-1-cyclohexanol

Base Information

• Chemical Name: trans-2-Phenyl-1-cyclohexanol
• CAS No.: 2362-61-0
• Molecular Formula: C12H16O
• Molecular Weight: 176.258
• Hs Code.: 2906290090
• European Community (EC) Number: 219-111-2
• UNII: 452WZ637M8,O5411L8484
• DSSTox Substance ID: DTXSID6022185
• Nikkaji Number: J209.407J
• Wikipedia: Trans-2-Phenyl-1-cyclohexanol
• Wikidata: Q81983865
• Mol file: 2362-61-0.mol

Synonyms:2-phenyl-1-cyclohexanol;trans-2-phenyl-1-cyclohexanol

Chemical Property of trans-2-Phenyl-1-cyclohexanol

Chemical Property:

• Vapor Pressure: 0.00203mmHg at 25°C
• Melting Point: 53-55 °C(lit.)
• Refractive Index: 1.553
• Boiling Point: 278.5 °C at 760 mmHg
• PKA: 15.05±0.40(Predicted)
• Flash Point: 113.3 °C
• PSA: 20.23000
• Density: 1.051 g/cm³
• LogP: 2.70510
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 176.120115130
• Heavy Atom Count: 13
• Complexity: 149

Purity/Quality:

98% ^*data from raw suppliers

trans-2-Phenyl-1-cyclohexanol ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CCC(C(C1)C2=CC=CC=C2)O
• Isomeric SMILES: C1CC[C@H]([C@@H](C1)C2=CC=CC=C2)O
• Uses: trans-2-Phenyl-1-cyclohexanol was used as a chiral derivatizing reagent to determine absolute configuration of α-chiral carboxylic acids by 1H NMR. Also, it was used for studying QSARs for baseline toxicity.

Technology Process of trans-2-Phenyl-1-cyclohexanol

There total 74 articles about trans-2-Phenyl-1-cyclohexanol 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: 96.0%

cyclohexane-1,2-epoxide (286-20-4) + phenyllithium (591-51-5) → trans-2-Phenylcyclohexanol (2362-61-0)

Guidance literature:

With boron trifluoride diethyl etherate; In tetrahydrofuran; hexane; at -78 ℃; for 0.166667h;

DOI:10.1021/ja00324a060

Reference yield: 95.0%

potassium trifluoro((1R*,2R*)-2-phenylcyclohexyl)borate → trans-2-Phenylcyclohexanol (2362-61-0)

Guidance literature:

With rose bengal; triethylamine; In ethanol; at 25 ℃; for 12h; Schlenk technique; Irradiation;

DOI:10.1021/acs.orglett.8b02095

Reference yield: 95.0%

cyclohexane-1,2-epoxide (286-20-4) + phenylmagnesium bromide → trans-2-Phenylcyclohexanol (2362-61-0)

Guidance literature:

With copper(l) iodide; In tetrahydrofuran; diethyl ether; at 20 ℃; for 7h;

DOI:10.1016/j.tetasy.2005.07.033

upstream raw materials:

(RS)-2-phenylcyclohexanone

cyclohexane-1,2-epoxide

phenyllithium

2-Phenylphenol

Downstream raw materials:

(RS)-2-phenylcyclohexanone

5-benzoylvaleric acid

1-Phenylcyclohexene

3-phenyl-1-cyclohexene

Refernces

Asymmetric Diels-Alder addition of cyclopentadiene to chiral naphthoquinones

10.1016/S0957-4166(98)00087-1

The research focuses on the asymmetric Diels–Alder addition of cyclopentadiene to chiral 1,4-naphthoquinones, with the aim of achieving high levels of diastereomeric excess. The purpose of this study was to develop a method for the stereoselective formation of cyclopentannulated products, which can be further transformed into pyranonaphthoquinones, a class of compounds related to the pyranonaphthoquinone antibiotics. The researchers used various chiral auxiliaries, including (R)-pantolactone, (S)-N-methyl-2-hydroxysuccinimide, and trans-2-phenylcyclohexanol, which when combined with Lewis acid conditions, led to significant asymmetric induction. The conclusions drawn from the study were that the use of chiral auxiliaries at C-2 of 1,4-naphthoquinones enabled up to 96% stereoinduction in Diels–Alder cycloadditions with cyclopentadiene. The chiral auxiliaries could be removed from the fragmented products in acceptable yields, allowing for the formation of cyclopentannulated pyranonaphthoquinone ring systems, similar to those found in nature.

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