15,16-Dir-8(17),11-labdadien-13-one

Base Information

• Chemical Name: 15,16-Dir-8(17),11-labdadien-13-one
• CAS No.: 76497-69-3
• Molecular Formula: C18H28O
• Molecular Weight: 260.42
• Mol file: 76497-69-3.mol

Synonyms:(3E)-4-[(1S,4aS,8aS)-5,5,8a-Trimethyl-2-methylenedecahydro-1-naphthalenyl]-3-buten-2-one;

Chemical Property of 15,16-Dir-8(17),11-labdadien-13-one

Chemical Property:

• Melting Point: 139.5 - 141 °C
• Boiling Point: 343.9±21.0 °C(Predicted)
• PSA: 17.07000
• Density: 0.94±0.1 g/cm3(Predicted)
• LogP: 4.93040

Purity/Quality:

98%min ^*data from raw suppliers

15,16-Dinor-8(17),11-labdadien-13-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 15,16-Dir-8(17),11-labdadien-13-one

There total 4 articles about 15,16-Dir-8(17),11-labdadien-13-one 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: 58.0%

labda-8(17),12-diene (76467-03-3) → (11E)-14,15-bisnorlabda-8(17),11-dien-13-one (76497-69-3) + (11E)-labda-8(17),11-dien-13-ol (76467-05-5,76497-67-1) + (12S)-labda-8(17),13(16)-dien-12-ol (76467-07-7) + (12R)-labda-8(17),13(16)-dien-12-ol (76467-06-6)

Guidance literature:

With oxygen; rose bengal; triethyl phosphite; Yield given. Multistep reaction. Further byproducts given; 1.) CH₂Cl₂, CH₃OH, irradiation, 2 h;

DOI:10.1021/jo00320a027

Reference yield:

epimanool (596-85-0) → (11E)-14,15-bisnorlabda-8(17),11-dien-13-one (76497-69-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 3.84 g / tosylhydrazide, sat. K₂CO₃ sol. / 2-methoxy-ethanol / 45 h / 95 - 100 °C

2: 0.47 g / POCl₃ / pyridine / 24 h / 0 °C

3: 1.) oxygen, rose bengal, 2.) triethyl phosphite / 1.) CH₂Cl₂, CH₃OH, irradiation, 2 h

With oxygen; rose bengal; potassium carbonate; toluene-4-sulfonic acid hydrazide; triethyl phosphite; trichlorophosphate; In pyridine; 2-methoxy-ethanol;

DOI:10.1021/jo00320a027

Reference yield:

14,15-dihydromanool (40768-86-3) → (11E)-14,15-bisnorlabda-8(17),11-dien-13-one (76497-69-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 0.47 g / POCl₃ / pyridine / 24 h / 0 °C

2: 1.) oxygen, rose bengal, 2.) triethyl phosphite / 1.) CH₂Cl₂, CH₃OH, irradiation, 2 h

With oxygen; rose bengal; triethyl phosphite; trichlorophosphate; In pyridine;

DOI:10.1021/jo00320a027

upstream raw materials:

labda-8⁽¹⁷⁾,12-diene

epimanool

14,15-dihydromanool

Refernces