2,6,6-Trimethylcyclohexene-1-methanol

Base Information

• Chemical Name: 2,6,6-Trimethylcyclohexene-1-methanol
• CAS No.: 472-20-8
• Molecular Formula: C10H18 O
• Molecular Weight: 154.252
• European Community (EC) Number: 207-449-3
• UNII: XD3YT58R9H
• DSSTox Substance ID: DTXSID60197061
• Nikkaji Number: J11.884B
• Wikidata: Q83070035
• Metabolomics Workbench ID: 163842
• Mol file: 472-20-8.mol

Synonyms:472-20-8;2,6,6-Trimethylcyclohexene-1-methanol;(2,6,6-TRIMETHYLCYCLOHEX-1-EN-1-YL)METHANOL;BETA-CYCLOGERANIOL;(2,6,6-trimethylcyclohexen-1-yl)methanol;1-Cyclohexene-1-methanol, 2,6,6-trimethyl-;.beta.-Cyclogeraniol;EINECS 207-449-3;AI3-37228;Cyclogeraniol;1-Cyclohexene-1-methanol,2,6,6-trimethyl-;B-Cyclogeraniol;beta -Cyclogeraniol;2,6,6-Trimethyl-1-cyclohexene-1-methanol;XD3YT58R9H;SCHEMBL4666701;DTXSID60197061;CHEBI:167402;MFCD09840290;SK-039;AKOS006329213;HY-W024698;SB84197;AS-65066;(2,6,6-trimethylcyclohex-1-enyl)methanol;CS-0061209;FT-0665339;FT-0665340;W17219;EN300-6767278;2,6,6-trimethyl-1-cyclohexene-1-methanol, AldrichCPR;Z1198234378;6KX

Chemical Property of 2,6,6-Trimethylcyclohexene-1-methanol

Chemical Property:

• Vapor Pressure: 0.0455mmHg at 25°C
• Melting Point: 43.5°C
• Refractive Index: 1.4870
• Boiling Point: 209.8°Cat760mmHg
• PKA: 14.85±0.10(Predicted)
• Flash Point: 88.1°C
• PSA: 20.23000
• Density: 0.893g/cm³
• LogP: 2.50530
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 154.135765193
• Heavy Atom Count: 11
• Complexity: 177

Purity/Quality:

99%, ^*data from raw suppliers

β-Cyclogeraniol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(CCC1)(C)C)CO
• Uses: β-Cyclogeraniol (cas# 472-20-8) is a compound useful in organic synthesis.

Technology Process of 2,6,6-Trimethylcyclohexene-1-methanol

There total 9 articles about 2,6,6-Trimethylcyclohexene-1-methanol 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: 100.0%

2,6,6-trimethylcyclohex-1-enecarbaldehyde (432-25-7) → β-cyclogeraniol (472-20-8)

Guidance literature:

2,6,6-trimethylcyclohex-1-enecarbaldehyde; With sodium tetrahydroborate; In methanol; at 0 ℃; Inert atmosphere;

With water; In methanol;

Reference yield: 56.0%

(E)-β-ionone (79-77-6,14901-07-6) → β-cyclogeraniol (472-20-8)

Guidance literature:

(E)-β-ionone; With ozone; In methanol; at -78 ℃;

With sodium tetrahydroborate; In methanol; at -78 - 20 ℃;

DOI:10.1021/jo960463g

Reference yield:

(E)-3-(2,6,6-Trimethyl-cyclohex-1-enyl)-acrylic acid methyl ester (15356-72-6) → β-cyclogeraniol (472-20-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: O₃ / methanol / 2.5 h / -78 °C

1.2: 93 percent / Zn; AcOH / H₂O

2.1: 76 percent / NaBH₄ / methanol / 13 h / 0 - 25 °C

With sodium tetrahydroborate; ozone; In methanol;

DOI:10.1002/anie.200460259

upstream raw materials:

2,6,6-trimethylcyclohex-1-enecarbaldehyde

aluminum isopropoxide

isopropyl alcohol

(E)-β-ionone

Downstream raw materials:

15,15'-didehydro-β,β-carotene

ethyl retinoate

(2,2,6-trimethylbicyclo<4.1.0>hept-1-yl)methanol

2-(bromomethyl)-1,3,3-trimethylcyclohex-1-ene

Refernces

• 1、 -. "BORONIC ESTER PRODRUGS AND USES THEREOF". Paragraph 0405-0406. . Retrieved 2020/12/07.
• 2、 Kozio?, Agata,Macegoniuk, Katarzyna,Grela, Ewa,Grabowiecka, Agnieszka,Biernat, Monika,Lochyński, Stanis?aw. "Synthesis of terpenoid oxo derivatives with antiureolytic activity". . p. 51 - 58. Retrieved 2018/11/01.