6,6-dibromobicyclo[3.1.0]hexan-3-one (2R,3R)-2,3-dibenzylethylene ketal

Base Information

• Chemical Name: 6,6-dibromobicyclo[3.1.0]hexan-3-one (2R,3R)-2,3-dibenzylethylene ketal
• CAS No.: 915149-82-5
• Molecular Formula: C₂₂H₂₂Br₂O₂
• Molecular Weight: 478.223
• Mol file: 915149-82-5.mol

Synonyms:6,6-dibromobicyclo[3.1.0]hexan-3-one (2R,3R)-2,3-dibenzylethylene ketal

Chemical Property of 6,6-dibromobicyclo[3.1.0]hexan-3-one (2R,3R)-2,3-dibenzylethylene ketal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6,6-dibromobicyclo[3.1.0]hexan-3-one (2R,3R)-2,3-dibenzylethylene ketal

There total 7 articles about 6,6-dibromobicyclo[3.1.0]hexan-3-one (2R,3R)-2,3-dibenzylethylene ketal 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: 78.0%

(2R,3R)-2,3-dibenzyl-1,4-dioxaspiro[4.4]non-7-ene (915149-80-3) + Bromoform (75-25-2) → 6,6-dibromobicyclo[3.1.0]hexan-3-one (2R,3R)-2,3-dibenzylethylene ketal (915149-82-5)

Guidance literature:

With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; In dichloromethane; at 18 ℃; for 2h; sonication;

DOI:10.1021/ol062020x

Reference yield:

(2R,3R)-2,2-diallyl-4,5-dibenzyl-[1,3]dioxolane (915149-78-9) → 6,6-dibromobicyclo[3.1.0]hexan-3-one (2R,3R)-2,3-dibenzylethylene ketal (915149-82-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / Grubbs' second-generation catalyst / CH₂Cl₂ / 5 h / 40 °C

2: 78 percent / benzyltriethylammonium chloride; aq. sodium hydroxide / CH₂Cl₂ / 2 h / 18 °C / sonication

With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane;

DOI:10.1021/ol062020x

Reference yield:

allylbenzene (300-57-2,57807-91-7) → 6,6-dibromobicyclo[3.1.0]hexan-3-one (2R,3R)-2,3-dibenzylethylene ketal (915149-82-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 89 percent / Grubbs' first-generation catalyst / CH₂Cl₂ / 18 h / 40 °C

2: 89 percent / potassium ferricyanide; potassium carbonate; AD-mix-β / osmium tetroxide; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 48 h / 18 °C

3: 72 percent / p-toluenesulfonic acid / benzene / 18 h / 80 °C

4: 94 percent / Grubbs' second-generation catalyst / CH₂Cl₂ / 5 h / 40 °C

5: 78 percent / benzyltriethylammonium chloride; aq. sodium hydroxide / CH₂Cl₂ / 2 h / 18 °C / sonication

With sodium hydroxide; AD-mix-β; N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate; toluene-4-sulfonic acid; potassium hexacyanoferrate(III); tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; osmium(VIII) oxide; Grubbs catalyst first generation; methanesulfonamide; In dichloromethane; water; tert-butyl alcohol; benzene;

DOI:10.1021/ol062020x

upstream raw materials:

(2R,3R)-2,3-dibenzyl-1,4-dioxaspiro[4.4]non-7-ene

Bromoform

(2R,3R)-2,2-diallyl-4,5-dibenzyl-[1,3]dioxolane

allylbenzene

Downstream raw materials:

(2'R,3'R,7'S)-3-{8'-bromo-2',3'-dibenzyl-1',4'-dioxaspiro[4.5]dec-8'-en-7'-yl}indole

(2'R,3'R,7'R)-3-{8'-bromo-2,3-dibenzyl-1',4'-dioxaspiro[4.5]dec-8'-en-7'-yl}indole

Refernces