3,7-Dimethyloct-6-en-1-yn-3-ol

Base Information

• Chemical Name: 3,7-Dimethyloct-6-en-1-yn-3-ol
• CAS No.: 29171-20-8
• Deprecated CAS: 5663-88-7,62055-34-9
• Molecular Formula: C10H16 O
• Molecular Weight: 152.236
• Hs Code.: 2905290000
• European Community (EC) Number: 249-482-6
• UNII: L06OT2435M
• DSSTox Substance ID: DTXSID6057588
• Nikkaji Number: J37.640J
• Wikidata: Q27893849
• Metabolomics Workbench ID: 45358
• Mol file: 29171-20-8.mol

Synonyms:3,7-dimethyloct-6-en-1-yn-3-ol;dehydro-beta-linalool;dehydrolinalool

Chemical Property of 3,7-Dimethyloct-6-en-1-yn-3-ol

Chemical Property:

• Vapor Pressure: 0.0141mmHg at 25°C
• Refractive Index: 1.477
• Boiling Point: 228.6°C at 760 mmHg
• Flash Point: 167°C
• PSA: 20.23000
• Density: 0.904g/cm³
• LogP: 2.11700
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 152.120115130
• Heavy Atom Count: 11
• Complexity: 190

Purity/Quality:

99.9% ^*data from raw suppliers

3,7-Dimethyl-6-octen-1-yn-3-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): A poison by ingestion. A mild skin and moderate eye irritant.
• Hazard Codes: A poison by ingestion. A mild skin and moderate eye irritant.

MSDS Files:

Useful:

• Chemical Classes: Other Classes -> Other Organic Compounds
• Canonical SMILES: CC(=CCCC(C)(C#C)O)C
• Uses: 3,7-Dimethyl-6-octen-1-yn-3-ol is a useful synthetic intermediate in the synthesis of Methylisopseudoionone (M314920); a derivative of Ionone (I731275) which is an aroma compound found in essential oils such as rose oil, and thus can be used in the perfumery industry.

Technology Process of 3,7-Dimethyloct-6-en-1-yn-3-ol

There total 21 articles about 3,7-Dimethyloct-6-en-1-yn-3-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: 99.1%

6-Methyl-hept-5-en-2-on (110-93-0,129085-68-3) + acetylene (74-86-2,25067-58-7) → 3,7-dimethyloct-6-en-1-yn-3-ol (29171-20-8)

Guidance literature:

With sodium methylate; In methanol; at 0 - 5 ℃; for 0.5h; Inert atmosphere;

Reference yield: 98.0%

(2S,3R)-3-(chloromethyl)-2-methyl-2-(4-methylpent-3-en-1-yl)oxirane (79194-57-3,91423-23-3) → (S)-3,7-dimethyloct-6-en-1-yn-3-ol (29171-20-8,62055-34-9,68224-83-9,125411-11-2)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -40 ℃; for 2h; Inert atmosphere;

DOI:10.1002/anie.201000890

Reference yield: 95.0%

6-Methyl-hept-5-en-2-on (110-93-0,129085-68-3) + acetylenemagnesium bromide (4301-14-8) → 3,7-dimethyloct-6-en-1-yn-3-ol (29171-20-8)

Guidance literature:

In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1021/ja012450c

upstream raw materials:

6-Methyl-hept-5-en-2-on

sodium acetylide

acetylene

acetylenemagnesium bromide

Downstream raw materials:

2-ethynyl-2,6,6-trimethyl-3,4,5,6-tetrahydro-(2H)-pyran

3,7-dimethylocta-1,6-dien-3-ol

3,7-dimethyloct-6-en-1-yn-3-yl acetate

3-(1-ethoxy-ethoxy)-3,7-dimethyl-oct-6-en-1-yne

Refernces

• 1、 Wu, Zhenhua,Suppo, Jean-Simon,Tumova, Sarka,Strope, Jonathan,Bravo, Fernando,Moy, Melody,Weinstein, Ethan S.,Peer, Cody J.,Figg, William D.,Chain, William J.,Echavarren, Antonio M.,Beech, David J.,Beutler, John A.. "Bridgehead Modifications of Englerin A Reduce TRPC4 Activity and Intravenous Toxicity but not Cell Growth Inhibition". supporting information. p. 1711 - 1716. Retrieved 2020/10/19.
• 2、 -. "ENGLERIN DERIVATIVES FOR TREATMENT OF CANCER". Paragraph 0095; 0099. . Retrieved 2019/01/21.