(+)-Dihydrocarveol

Base Information

• Chemical Name: (+)-Dihydrocarveol
• CAS No.: 22567-21-1
• Deprecated CAS: 17699-09-1,73804-29-2
• Molecular Formula: C10H18 O
• Molecular Weight: 154.252
• Hs Code.: 2906199090
• European Community (EC) Number: 253-755-5,245-085-7
• UNII: R6OW1F785H,ZR76810L52
• DSSTox Substance ID: DTXSID001030862,DTXSID40904694
• Nikkaji Number: J259.613J
• Wikidata: Q27104757
• Metabolomics Workbench ID: 28126
• Mol file: 22567-21-1.mol

Synonyms:2-methyl-5-(1-methylethenyl)cyclohexanol;2-methyl-5-(1-methylvinyl)cyclohexan-1-ol;dihydrocarveol

Chemical Property of (+)-Dihydrocarveol

Chemical Property:

• Vapor Pressure: 0.0177mmHg at 25°C
• Refractive Index: n20/D 1.476
• Boiling Point: 225oC at 760 mmHg
• PKA: 15.20±0.60(Predicted)
• Flash Point: 91.7oC
• PSA: 20.23000
• Density: 0.926 g/mL at 20oC(lit.)
• LogP: 2.35960
• Storage Temp.: 2-8°C
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 154.135765193
• Heavy Atom Count: 11
• Complexity: 151

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC(CC1O)C(=C)C
• Isomeric SMILES: C[C@H]1CC[C@@H](C[C@@H]1O)C(=C)C

Technology Process of (+)-Dihydrocarveol

There total 44 articles about (+)-Dihydrocarveol 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: 88.0%

(-)-dihydrocarvone (5524-05-0,619-02-3) → (1S,2S,5S)-5-isopropenyl-2-methylcyclohexan-1-ol (22567-21-1,17699-09-1) + (1R,2S,5S)-5-isopropenyl-2-methylcyclohexan-1-ol (22567-22-2,17699-09-1)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at -78 ℃; for 0.25h;

DOI:10.1002/anie.200462268

Reference yield: 49.0%

(R)-dihydrocarvone (116499-64-0) → (+)-neodihydrocarveol (20549-48-8,17699-09-1) + (1R,2R,4R)-dihydrocarveol (619-01-2,18675-33-7,18675-34-8,18675-35-9,20549-48-8,22567-21-1,22567-22-2,36237-64-6,38049-26-2,51773-45-6,53796-77-3,53796-80-8,73804-29-2,20549-47-7,17699-09-1) + (1R,2S,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohexanol (51773-45-6,17699-09-1)

Guidance literature:

(R)-dihydrocarvone; With C₁₃H₂₃BN₂; In benzene-d6; toluene; at 25 ℃; for 1h; Inert atmosphere; Schlenk technique; Glovebox;

With acetic acid; In diethyl ether; water; chemoselective reaction; Inert atmosphere; Schlenk technique; Glovebox;

DOI:10.1021/acs.orglett.9b02515

Reference yield: 1.6%

(R)-Carvone (6485-40-1,2244-16-8) → (2R,5R)-5-isopropenyl-2-methylcyclohexanone (5524-05-0) + (+)-neodihydrocarveol (20549-48-8,17699-09-1) + (1R,2R,4R)-dihydrocarveol (619-01-2,18675-33-7,18675-34-8,18675-35-9,20549-48-8,22567-21-1,22567-22-2,36237-64-6,38049-26-2,51773-45-6,53796-77-3,53796-80-8,73804-29-2,20549-47-7,17699-09-1) + dihydrocarveol (36237-64-6,17699-09-1) + (+)-isodihydrocarvone (619-02-3,3792-53-8,4584-09-2,5524-05-0,5948-04-9,7764-50-3,53796-79-5,69460-46-4,116499-64-0,6909-25-7) + (1R,2S,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohexanol (51773-45-6,17699-09-1)

Guidance literature:

In various solvent(s); at 25 ℃; for 240h; Product distribution; Mechanism; rotary shaker (70 rpm), dark, suspension cells of Nicotiana tabacum; different starting substrates;

DOI:10.1016/0031-9422(82)85179-0

upstream raw materials:

(2R,5R)-5-isopropenyl-2-methylcyclohexanone

(R)-Carvone

oxime (4R)-4-isopropenyl-1-methylcyclohex-1-en-6-one

oxime (4S)-4-isopropenyl-1-methylcyclohex-1-en-6-one

Downstream raw materials:

(1R,3R,5R)-1-(3-Hydroxy-4-methylcyclohexyl)ethanone

limonene.

Dihydrocarveol-tosylat

(+)-(1S,2S,5S)-carvomenthyl tosylate

Refernces

• 1、 Phillips, Nicholas A.,O'hanlon, James,Hooper, Thomas N.,White, Andrew J. P.,Crimmin, Mark R.. "Dihydridoboranes: Selective Reagents for Hydroboration and Hydrodefluorination". supporting information. p. 7289 - 7293. Retrieved 2019/10/08.
• 2、 Guo, Jiyang,Zhang, Rui,Ouyang, Jingping,Zhang, Feiting,Qin, Fengyu,Liu, Guigao,Zhang, Wenhe,Li, Hengyu,Ji, Xiaohong,Jia, Xian,Qin, Bin,You, Song. "Stereodivergent Synthesis of Carveol and Dihydrocarveol through Ketoreductases/Ene-Reductases Catalyzed Asymmetric Reduction". . p. 5496 - 5504. Retrieved 2018/11/30.