9,10-Epoxy-2,6-humuladiene

Base Information

• Chemical Name: 9,10-Epoxy-2,6-humuladiene
• CAS No.: 21624-36-2
• Molecular Formula: C15H24O
• Molecular Weight: 220.35
• Mol file: 21624-36-2.mol

Synonyms:

Chemical Property of 9,10-Epoxy-2,6-humuladiene

Chemical Property:

• Boiling Point: 294.9±29.0 °C(Predicted)
• Density: 0.896±0.06 g/cm3(Predicted)

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 9,10-Epoxy-2,6-humuladiene

There total 5 articles about 9,10-Epoxy-2,6-humuladiene 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%

((4E,8E)-(1R,11S)-2,2,9-Trimethyl-12-oxa-bicyclo[9.1.0]dodeca-4,8-dien-5-yl)-methanol (87161-79-3) → (3E,7Z)-(1S,11R)-3,7,10,10-Tetramethyl-12-oxa-bicyclo[9.1.0]dodeca-3,7-diene (21624-36-2,69880-55-3,73951-53-8,87205-68-3)

Guidance literature:

With 2,3,5-trimethyl-pyridine; lithium aluminium tetrahydride; methanesulfonyl chloride; lithium chloride;

DOI:10.1016/S0040-4039(00)88046-6

Reference yield: 57.0%

2S*,3S*,6S*,7S*,9S*,10S*-humulene 2,3;6,7;9,10-triepoxide (60545-11-1,108101-56-0) → humulene 9,10-epoxide (21624-36-2,69880-55-3,73951-53-8,87205-68-3)

Guidance literature:

With n-butyllithium; tungsten(VI) chloride; In tetrahydrofuran; hexane; for 2h; Ambient temperature;

DOI:10.1021/jo00043a033

Reference yield:

(Z,E,E)-humulen-12-al 6,7-epoxide (86331-54-6,86362-98-3) → (3E,7Z)-(1S,11R)-3,7,10,10-Tetramethyl-12-oxa-bicyclo[9.1.0]dodeca-3,7-diene (21624-36-2,69880-55-3,73951-53-8,87205-68-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 91 percent / mCPBA

2: 96 percent / NaBH₄

3: 82 percent / TiCl₃/LAH

4: 95 percent / MsCL/collidine/LiCl, LiAlH₄

With 2,3,5-trimethyl-pyridine; sodium tetrahydroborate; lithium aluminium tetrahydride; titanium(III) chloride; methanesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; lithium chloride;

DOI:10.1016/S0040-4039(00)88046-6

upstream raw materials:

((4E,8E)-(1R,11S)-2,2,9-Trimethyl-12-oxa-bicyclo[9.1.0]dodeca-4,8-dien-5-yl)-methanol

(Z,E,E)-humulen-12-al 6,7-epoxide

((E)-(1R,3S,5R,12S)-3,11,11-Trimethyl-4,13-dioxa-tricyclo[10.1.0.0^3,5]tridec-8-en-8-yl)-methanol

(E)-(1R,3S,5R,12S)-3,11,11-Trimethyl-4,13-dioxa-tricyclo[10.1.0.0^3,5]tridec-8-ene-8-carbaldehyde

Downstream raw materials:

(+/-)-bicyclohumulenone

(+/-)-Africanol

Humulenol-II

4,8,11,11-tetramethyltricyclo<7.2.0.0^2,4>undecane-5,8-diol

Refernces

• 1、 Yang, Xiaogen,Deinzer, Max L.. "Hydrolysis and Reversible Isomerization of Humulene Epoxides II and III". . p. 4717 - 4722. Retrieved 2007/10/02.