5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Base Information

• Chemical Name: 5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
• CAS No.: 1196033-40-5
• Molecular Formula: C₁₉H₂₃BO₆
• Molecular Weight: 358.199

Synonyms:5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Chemical Property of 5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

2,2-Dimethyl-5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylidene)-1,3-dioxane-4,6-dione ^*data from reagent suppliers

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Technology Process of 5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

There total 1 articles about 5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 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: 72.0%

cycl-isopropylidene malonate (2033-24-1) + 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde (128376-64-7) → 5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (1196033-40-5)

Guidance literature:

With pyrrolidine acetic acid; In benzene; at 50 ℃; Inert atmosphere;

DOI:10.1021/ol902216y

Reference yield: 81.0%

5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (1196033-40-5) + 1-aza-5-stanna-5-methyl-bicylo{3.3.3}undecane (93253-75-9) → 2,2-dimethyl-5-(1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)-1,3-dioxane-4,6-dione

Guidance literature:

With tris(pentafluorophenyl)borate; In 1,2-dichloro-ethane; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1002/anie.201500983

Reference yield:

ethyl [(E)-3-(1,1,1-tributylstannyl)-2-propenyl] carbonate (1007392-16-6) + 5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (1196033-40-5) → (4R,2E)-4-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)but-2-enyl ethyl carbonate (1196033-55-2) + (4S,2E)-4-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)but-2-enyl ethyl carbonate

Guidance literature:

With silver hexafluoroantimonate; chlorobis(ethylene)rhodium(I) dimer; 5-methoxy-1,5-dimethyl-2-(2-(trifluoromethyl)phenyl)bicyclo[2.2.2]octa-2,7-diene; In tetrahydrofuran; at 10 ℃; for 45h; optical yield given as %ee; enantioselective reaction; Molecular sieve; Inert atmosphere;

DOI:10.1021/ol902216y

upstream raw materials:

cycl-isopropylidene malonate

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

Downstream raw materials:

(4R,2E)-4-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)but-2-enyl ethyl carbonate

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