1-but-3-enyl-4-[3,6-dimethoxy-2-(2-methyl-allyl)-phenyl]-3,6-dioxa-bicyclo[3.1.0]hexan-2-one

Base Information

• Chemical Name: 1-but-3-enyl-4-[3,6-dimethoxy-2-(2-methyl-allyl)-phenyl]-3,6-dioxa-bicyclo[3.1.0]hexan-2-one
• CAS No.: 916433-71-1
• Molecular Formula: C₂₀H₂₄O₅
• Molecular Weight: 344.408
• Mol file: 916433-71-1.mol

Synonyms:1-but-3-enyl-4-[3,6-dimethoxy-2-(2-methyl-allyl)-phenyl]-3,6-dioxa-bicyclo[3.1.0]hexan-2-one

Chemical Property of 1-but-3-enyl-4-[3,6-dimethoxy-2-(2-methyl-allyl)-phenyl]-3,6-dioxa-bicyclo[3.1.0]hexan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-but-3-enyl-4-[3,6-dimethoxy-2-(2-methyl-allyl)-phenyl]-3,6-dioxa-bicyclo[3.1.0]hexan-2-one

There total 9 articles about 1-but-3-enyl-4-[3,6-dimethoxy-2-(2-methyl-allyl)-phenyl]-3,6-dioxa-bicyclo[3.1.0]hexan-2-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: 83.0%

1-but-3-enyl-4-[3,6-dimethoxy-2-(2-methyl-allyl)-phenyl]-3,6-dioxa-bicyclo[3.1.0]hexan-2-one (916433-79-9) → 1-but-3-enyl-4-[3,6-dimethoxy-2-(2-methyl-allyl)-phenyl]-3,6-dioxa-bicyclo[3.1.0]hexan-2-one (916433-71-1)

Guidance literature:

With 2,6-diphenyl-4-nitrophenol; trimethylaluminum; In dichloromethane; for 36h;

DOI:10.1021/ja0662671

Reference yield: 80.0%

(3-but-3-enyl-3-hydroxymethyl-oxiranyl)-[3,6-dimethoxy-2-(2-methyl-allyl)-phenyl]-methanol (916433-72-2) → 1-but-3-enyl-4-[3,6-dimethoxy-2-(2-methyl-allyl)-phenyl]-3,6-dioxa-bicyclo[3.1.0]hexan-2-one (916433-71-1)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; In dichloromethane; for 20h;

DOI:10.1021/ja0662671

Reference yield:

3-(tert-butyldiphenylsilyloxy)hepta-2,6-dien-1-ol (916433-76-6) → 1-but-3-enyl-4-[3,6-dimethoxy-2-(2-methyl-allyl)-phenyl]-3,6-dioxa-bicyclo[3.1.0]hexan-2-one (916433-71-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 92 percent / (i-PrO)4Ti; 4 Angstroem molecular sieves; tert-butyl hydroperoxide / L-(+)-diethyl tartrate / CH₂Cl₂; decane / 48 h / -30 °C

2.1: 94 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.92 h / -78 °C

3.1: n-BuLi / petroleum ether; tetrahydrofuran / 0.5 h / -78 °C

3.2: petroleum ether; tetrahydrofuran / 1.75 h / -78 - 20 °C

3.3: 25 percent / petroleum ether; tetrahydrofuran / 0.33 h / -78 °C

4.1: 87 percent / TBAF / tetrahydrofuran / 1 h

5.1: 80 percent / PhI(OAc)2; TEMPO / CH₂Cl₂ / 20 h

With titanium(IV) isopropylate; tert.-butylhydroperoxide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; n-butyllithium; oxalyl dichloride; [bis(acetoxy)iodo]benzene; 4 A molecular sieve; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; diethyl (2R,3R)-tartrate; In tetrahydrofuran; decane; dichloromethane; Petroleum ether; 1.1: Sharpless epoxidation / 2.1: Swern oxidation;

DOI:10.1021/ja0662671

upstream raw materials:

1-but-3-enyl-4-[3,6-dimethoxy-2-(2-methyl-allyl)-phenyl]-3,6-dioxa-bicyclo[3.1.0]hexan-2-one

(3-but-3-enyl-3-hydroxymethyl-oxiranyl)-[3,6-dimethoxy-2-(2-methyl-allyl)-phenyl]-methanol

3-but-3-enyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxirane-2-carbaldehyde

3-(tert-butyldiphenylsilyloxy)hepta-2,6-dien-1-ol