4-Methyl-1-octyn-4-ol

Base Information

• Chemical Name: 4-Methyl-1-octyn-4-ol
• CAS No.: 22128-43-4
• Molecular Formula: C₉H₁₆O
• Molecular Weight: 140.225
• DSSTox Substance ID: DTXSID40447950
• Mol file: 22128-43-4.mol

Synonyms:4-methyl-1-octyn-4-ol;22128-43-4;4-methyloct-1-yn-4-ol;1-Octyn-4-ol, 4-methyl-;MFCD02660904;4-METHYLOCTIN-4-OL;4-hydroxy-4-methyl-1-octyne;SCHEMBL6152885;DTXSID40447950;VWNNGOBVFMFPNE-UHFFFAOYSA-N;XAA12843;AC1974;AKOS006277756;CS-12249;LS-98169;SY041514;CS-0449725;EN300-6398802

Chemical Property of 4-Methyl-1-octyn-4-ol

Chemical Property:

• Melting Point: -16°C (estimate)
• Refractive Index: 1.4395 (estimate)
• Boiling Point: 226.76°C (rough estimate)
• PKA: 14.36±0.29(Predicted)
• PSA: 20.23000
• Density: 0.8565 (estimate)
• LogP: 1.95090
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 140.120115130
• Heavy Atom Count: 10
• Complexity: 131

Purity/Quality:

99%, ^*data from raw suppliers

1-Octyn-4-ol,4-methyl- 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Moderately toxic by ingestion. A moderate eye irritant.
• Hazard Codes: Moderately toxic by ingestion. A moderate eye irritant. When heated to decomposition it emits acrid smoke and irritating vapors.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC(C)(CC#C)O

Technology Process of 4-Methyl-1-octyn-4-ol

There total 5 articles about 4-Methyl-1-octyn-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: 95.0%

n-hexan-2-one (591-78-6) + allenylmagnesium bromide (18295-60-8) → 4-methyl-4S-hydroxy-1-octyne (58683-10-6,70954-70-0,70954-71-1,22128-43-4)

Guidance literature:

In diethyl ether; at 25 ℃; for 4h;

DOI:10.1021/ol061596j

Reference yield: 71.4%

n-hexan-2-one (591-78-6) + propargyl bromide (106-96-7) → 4-methyl-4S-hydroxy-1-octyne (58683-10-6,70954-70-0,70954-71-1,22128-43-4)

Guidance literature:

With magnesium; In tetrahydrofuran; at 25 - 35 ℃; for 10h; Solvent; Industrial scale;

Reference yield:

n-hexan-2-one (591-78-6) + 2-allenyl-5,5-dimethyl-1,3,2-dioxaborinane (57186-58-0) → 4-methyl-4S-hydroxy-1-octyne (58683-10-6,70954-70-0,70954-71-1,22128-43-4) + 4-methylocta-1,2-dien-4-ol (136050-75-4)

Guidance literature:

With bis(bis(trimethylsilyl)amido)zinc(II); In tetrahydrofuran; at 25 ℃; for 36h; Overall yield = 65 %; regioselective reaction; Inert atmosphere;

DOI:10.1021/acs.orglett.5b03045

upstream raw materials:

n-hexan-2-one

propargyl bromide

allenylmagnesium bromide

propargyl magnesium bromide

Downstream raw materials:

(Z)-7-hydroxy-7-methyl-3-phenyl-N-p-tolylundec-2-en-4-ynamide

2-(4-hydroxy-4-methyloct-1-ynyl)-N-(4-methoxyphenyl)benzamide

dihydro-5-butyl-5-methyl-2-(3H)-furanone

5-Hydroxy-5-methyl-1-phenyl-non-2-in-1-on

Refernces

• 1、 Yamashita, Yasuhiro,Cui, Yi,Xie, Peizhong,Kobayashi, Shu. "Zinc Amide Catalyzed Regioselective Allenylation and Propargylation of Ketones with Allenyl Boronate". supporting information. p. 6042 - 6045. Retrieved 2016/01/09.
• 2、 Harikrishna,Mohan, H. Rama,Dubey,Subbaraju, Gottumukkala V.. "Synthesis of 2-normisoprostol, methyl6-(3-hydroxy-2-((E)-4-hydroxy-4- methyloct-1-enyl)-5-oxocyclopentyl)hexanoate". experimental part. p. 2763 - 2775. Retrieved 2009/12/06.