(1R,2E,4R,7E,11E)-1,7,11-trimethyl-4-propan-2-ylcyclotetradeca-2,7,11-trien-1-ol

Base Information

• Chemical Name: (1R,2E,4R,7E,11E)-1,7,11-trimethyl-4-propan-2-ylcyclotetradeca-2,7,11-trien-1-ol
• CAS No.: 25269-17-4
• Molecular Formula: C₂₀H₃₄O
• Molecular Weight: 290.489
• Wikidata: Q105345505
• Wikipedia: Cembratrienol

Synonyms:Thunbergol;25269-17-4

Chemical Property of (1R,2E,4R,7E,11E)-1,7,11-trimethyl-4-propan-2-ylcyclotetradeca-2,7,11-trien-1-ol

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 392.69°C at 760 mmHg
• PKA: 14.40±0.70(Predicted)
• Flash Point: 169.813°C
• PSA: 20.23000
• Density: 0.876g/cm³
• LogP: 5.81260
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 290.260965704
• Heavy Atom Count: 21
• Complexity: 400

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CCCC(C=CC(CCC(=CCC1)C)C(C)C)(C)O
• Isomeric SMILES: C/C/1=C\CC[C@@](/C=C/[C@H](CC/C(=C/CC1)/C)C(C)C)(C)O
• Uses: Isocembrol (cas# 25269-17-4) could have antibacterial and antifungal properties.

Technology Process of (1R,2E,4R,7E,11E)-1,7,11-trimethyl-4-propan-2-ylcyclotetradeca-2,7,11-trien-1-ol

There total 11 articles about (1R,2E,4R,7E,11E)-1,7,11-trimethyl-4-propan-2-ylcyclotetradeca-2,7,11-trien-1-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:

(1S,2E,4R,7E,11S,12S)-11,12-epoxy-2,6-cembradiene-4-ol (68042-99-9) → Isocembrol (4R) (25269-17-4,53494-49-8,63568-83-2,63568-84-3,68421-38-5,78087-96-4,79897-32-8,80126-41-6,121702-09-8,121702-10-1,121702-11-2) + (2E,7Z,11E)-(1R,4S)-4-Isopropyl-1,7,11-trimethyl-cyclotetradeca-2,7,11-trienol (78087-96-4)

Guidance literature:

With copper; zinc; In methanol; for 16h; Yield given. Yields of byproduct given; Heating;

DOI:10.1021/jo00334a036

Reference yield:

methyl magnesium iodide (917-64-6) + (1S)-18-norcembra-2Z,7E,11E-trien-4-one (121702-07-6) → Isocembrol (4R) (25269-17-4,53494-49-8,63568-83-2,63568-84-3,68421-38-5,78087-96-4,79897-32-8,80126-41-6,121702-09-8,121702-10-1,121702-11-2) + (1S,4R)-cembra-2Z,7E,11E-trien-4-ol (121702-09-8) + (1S,4S)-cembra-2Z,7E,11E-trien-4-ol (121702-10-1) + (1S,2E, 4S,7E,11E)-2,7,11-cembratriene-4-ol (80126-41-6)

Guidance literature:

In diethyl ether; at 8 ℃; for 20h;

DOI:10.1007/BF00596739

Reference yield:

(2E,7E,11E)-(S)-4-Isopropyl-7,11-dimethyl-cyclotetradeca-2,7,11-trienone (53343-10-5) → Isocembrol (4R) (25269-17-4,53494-49-8,63568-83-2,63568-84-3,68421-38-5,78087-96-4,79897-32-8,80126-41-6,121702-09-8,121702-10-1,121702-11-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 0.149 g / pentane / 4 h / Irradiation; high-pressure mercury lamp

2: 0.02 g / diethyl ether / 20 h / 8 °C

In diethyl ether; pentane;

DOI:10.1007/BF00596739

upstream raw materials:

methyl magnesium iodide

(1S)-18-norcembra-2Z,7E,11E-trien-4-one

(1S,4R)-cembra-2Z,7E,11E-trien-4-ol

(1S,2E,4R,7E,11S,12S)-11,12-epoxy-2,6-cembradiene-4-ol

Downstream raw materials:

5-Isopropyl-4,8,10a-trimethyl-1,2,3,4b,5,6,7,9,10,10a-decahydro-phenanthrene

5-Isopropyl-4,8,10a-trimethyl-1,2,4a,4b,5,6,7,9,10,10a-decahydro-phenanthrene

4-Isopropyl-1,5,8a-trimethyl-1,2,3,4,7,8,8a,9,10,10a-decahydro-phenanthrene

cembrene

Refernces

Synthesis of N-methyl urocanates of hydroxyderivatives of isocembrol

10.1007/s10600-007-0065-6

The research focuses on the synthesis of N-methyl urocanates of hydroxy derivatives of isocembrol, which are proposed biomimetics of taxol and exhibit cytotoxic activity similar to eleutherobin and sarcodictyins. The experiments involved stereospecific hydroxylation of isocembrol to prepare alcohols, which were then esterified into N-methylurocanates. Key reactants included isocembrol, t-butylhydroperoxide (TBHP), VO(acac)2, LiAlH4, (i-Bu)2AlH, SeO2, and N-methylurocanic acid, among others. The analyses used to characterize the products and intermediates were primarily nuclear magnetic resonance (NMR) spectroscopy, including both proton (PMR) and carbon (13C NMR) variants, as well as thin-layer chromatography (TLC), optical rotation measurements, and melting point determinations. These techniques were crucial in establishing the regio- and stereochemistry of the synthesized compounds.

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