2-Methyl-5-phenylpentanol

Base Information

• Chemical Name: 2-Methyl-5-phenylpentanol
• CAS No.: 25634-93-9
• Deprecated CAS: 75553-31-0,185019-20-9
• Molecular Formula: C12H18 O
• Molecular Weight: 178.274
• European Community (EC) Number: 405-890-8,687-586-7
• UNII: 2BH2T7C3MX
• DSSTox Substance ID: DTXSID70885306
• Nikkaji Number: J1.607.660K
• Wikidata: Q27254526
• Mol file: 25634-93-9.mol

Synonyms:2-methyl-5-phenylpentanol;rosaphen

Chemical Property of 2-Methyl-5-phenylpentanol

Chemical Property:

• Vapor Pressure: 0.00637mmHg at 25°C
• Refractive Index: 1.511
• Boiling Point: 267.9°Cat760mmHg
• PKA: 15.02±0.10(Predicted)
• Flash Point: 106.8°C
• PSA: 20.23000
• Density: 0.96g/cm³
• LogP: 2.63770
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 178.135765193
• Heavy Atom Count: 13
• Complexity: 116

Purity/Quality:

99.9% ^*data from raw suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 26-37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCCC1=CC=CC=C1)CO
• General Description: Rosaphen is a commercially important fragrance compound synthesized through an efficient "one-pot" reductive lactone alkylation method, which enables high-yield and enantiomerically pure production of chiral isoprenoid alcohols. This synthetic approach highlights its utility in creating structurally complex and valuable targets for the fragrance industry.

Technology Process of 2-Methyl-5-phenylpentanol

There total 13 articles about 2-Methyl-5-phenylpentanol 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%

(±)-2-methyl-5-phenylpentanoic acid (143097-60-3) → 2-methyl-5-phenyl pentanol (25634-93-9)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.molcatb.2010.07.019

Reference yield: 83.0%

N,N,2-trimethyl-5-phenylpentanamide → 2-methyl-5-phenyl pentanol (25634-93-9)

Guidance literature:

With sodium hydride; sodium iodide; zinc(II) iodide; In tetrahydrofuran; mineral oil; at 40 ℃; for 12h; Sealed tube;

DOI:10.1002/anie.201900233

Reference yield: 67.0%

carbon monoxide (201230-82-2) + 5-phenylpentan-1-ol (10521-91-2) → 2-methyl-5-phenyl pentanol (25634-93-9)

Guidance literature:

With [Mn(HN(C₂H₄PⁱPr₂)₂)(CO)₂Br]; hydrogen; sodium t-butanolate; In toluene; at 150 ℃; for 24h;

DOI:10.1039/d0sc05404f

upstream raw materials:

(4-methylpent-4-en-1-yl)benzene

2-methyl-5-phenyl-valeric acid ethyl ester

(E)-2-Methyl-5-phenyl-2-penten-1-ol

(Z)-2-methyl-5-phenylpent-2-en-1-ol

Downstream raw materials:

(5-chloro-4-methyl-pentyl)-benzene

5-cyclohexyl-2-methylpentanol

Refernces

"One-pot" reductive lactone alkylation provides a concise asymmetric synthesis of chiral isoprenoid targets

10.1021/ol401801g

The study presents an efficient "one-pot" reductive lactone alkylation method for synthesizing chiral isoprenoid compounds, which are significant structural fragments in natural products like pheromones, fragrances, and vitamins. The process involves nucleophilic addition of organometallic reagents, such as alkyllithiums or Grignard reagents, to lactones, followed by in situ reduction of the intermediate keto-alcohol using a modified Clemmensen reduction with TMSCl and Zn. The method was successfully applied to various lactones, including (R)-3-methylbutyrolactone and (R)-4-methyl-δ-valerolactone, derived from tigogenin, and demonstrated high yields and enantiomeric purity. The synthesized alcohols were further utilized to create commercially important compounds like the fragrance Rosaphen and the side chains of Zaragozic acid C and vitamin E, showcasing the versatility and potential for scale-up of this synthetic approach.

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