(4R)-2-methyl-6-methylideneocta-2,7-dien-4-ol

Base Information

• Chemical Name: (4R)-2-methyl-6-methylideneocta-2,7-dien-4-ol
• CAS No.: 60894-97-5
• Molecular Formula: C10H16 O
• Molecular Weight: 152.236
• DSSTox Substance ID: DTXSID501263967
• Nikkaji Number: J510.200F
• Wikidata: Q27158231
• Metabolomics Workbench ID: 28025
• Mol file: 60894-97-5.mol

Synonyms:(R)-Ipsdienol;R-ipsdienol;60894-97-5;(4R)-2-methyl-6-methylideneocta-2,7-dien-4-ol;2-Methyl-6-methylene-2,7-octadien-4R-ol;2,7-Octadien-4-ol, 2-methyl-6-methylene-, (4R)-;(4R)-ipsdienol;(R)-(-)-ipsdienol;(4R)-(-)-ipsdienol;SCHEMBL9629960;CHEBI:84970;DTXSID501263967;LMPR0102010026;C20943;(4R)-2-Methyl-6-methylene-2,7-octadien-4-ol;(4R)-2-Methyl-6-methyleneocta-2,7-dien-4-ol;(4R)-2-methyl-6-methyloctadeca-2,7-dien-4ol;Q27158231

Chemical Property of (4R)-2-methyl-6-methylideneocta-2,7-dien-4-ol

Chemical Property:

• Vapor Pressure: 0.0103mmHg at 25°C
• Boiling Point: 233.6°Cat760mmHg
• Flash Point: 92.2°C
• PSA: 20.23000
• Density: 0.87g/cm³
• LogP: 2.44580
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 152.120115130
• Heavy Atom Count: 11
• Complexity: 173

Purity/Quality:

99% ^*data from raw suppliers

R-Ipsdienol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CC(CC(=C)C=C)O)C
• Isomeric SMILES: CC(=C[C@@H](CC(=C)C=C)O)C
• Uses: R-Ipsdienol is an isomer of S-Ipsdienol (I747508). S-Ipsdienol is a terpene, which is a conspecific aggregation pheromone of the Asian larch bark beetle, Ips subelongatus. S-Ipsdienol could be used as an antioxidant and antimicrobial agent in food, pharmaceutical and pesticide industries.

Technology Process of (4R)-2-methyl-6-methylideneocta-2,7-dien-4-ol

There total 6 articles about (4R)-2-methyl-6-methylideneocta-2,7-dien-4-ol 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:

3,3-dimethyl acrylaldehyde (107-86-8) + tributyl(2-methylene-but-3-enyl)stannane → (R)-(-)-2-Methyl-6-methylene-2,7-octadien-4-ol (60894-97-5) + (4S)-2-methyl-6-methylideneocta-2,7-dien-4-ol (35628-00-3)

Guidance literature:

With titanium(IV) isopropylate; (i-C₃H₇)SB(C₂H₅)2; (R)-1,1'-Bi-2-naphthol; In various solvent(s); at -20 ℃; for 5h; Title compound not separated from byproducts.;

DOI:10.1002/1099-0690(200103)2001:6<1143::aid-ejoc1143>3.0.co;2-o

Reference yield:

3,3-dimethyl acrylaldehyde (107-86-8) + 4,4,5,5-tetramethyl-2-(2-methylenebut-3-enyl)-1,3,2-dioxaborolane (1335316-66-9) → (R)-(-)-2-Methyl-6-methylene-2,7-octadien-4-ol (60894-97-5) + (4S)-2-methyl-6-methylideneocta-2,7-dien-4-ol (35628-00-3)

Guidance literature:

With (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid; In tetrachloromethane; toluene; at -40 ℃; for 26h; Overall yield = 75 %; Overall yield = 11.4 mg; enantioselective reaction; Molecular sieve; Inert atmosphere;

DOI:10.1002/adsc.201900203

Reference yield:

2-Methyl-6-methylene-2,7-octadien-4-one (539-70-8) → (R)-(-)-2-Methyl-6-methylene-2,7-octadien-4-ol (60894-97-5) + (4S)-2-methyl-6-methylideneocta-2,7-dien-4-ol (35628-00-3)

Guidance literature:

In tetrahydrofuran; at -100 ℃; for 72h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; complex of LiAlH₄ with (R)-(+)-2,2'-dihydroxy-1,1'-binaphthyl;

upstream raw materials:

L-(+)-diisopropyl tartrate

3,3-dimethyl acrylaldehyde

dimethoxyisoprenylborane

2-Methyl-6-methylene-2,7-octadien-4-one

Refernces

• 1、 Kovalenko,Prokhorevich. "Improved synthesis of optically active ipsdienol". . p. 757 - 758. Retrieved 2016/07/06.
• 2、 -. "Intermediates useful for the chiral isoprenylation of aldehydes". . . Retrieved 2008/06/13.