4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3-CYCLOHEXENE-1-CARBOXYLIC ACID METHYL ESTER

Base Information

• Chemical Name: 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3-CYCLOHEXENE-1-CARBOXYLIC ACID METHYL ESTER
• CAS No.: 151075-20-6
• Molecular Formula: C14H23BO4
• Molecular Weight: 266.145
• Hs Code.: 2934999090
• Mol file: 151075-20-6.mol

Synonyms:4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3-CYCLOHEXENE-1-CARBOXYLIC ACID METHYL ESTER;Methyl 4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-enecarboxylate;methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-ene-1-carboxylate

Chemical Property of 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3-CYCLOHEXENE-1-CARBOXYLIC ACID METHYL ESTER

Chemical Property:

• Boiling Point: 295.5±50.0 °C(Predicted)
• PSA: 44.76000
• Density: 1.04±0.1 g/cm3(Predicted)
• LogP: 2.51730
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C

Purity/Quality:

97% ^*data from raw suppliers

4-(Methoxycarbonyl)cyclohexene-1-boronicacidpinacolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 4-(Methoxycarbonyl)cyclohexene-1-boronic acid pinacol ester

Technology Process of 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3-CYCLOHEXENE-1-CARBOXYLIC ACID METHYL ESTER

There total 2 articles about 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3-CYCLOHEXENE-1-CARBOXYLIC ACID METHYL ESTER 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: 51.0%

methyl 4-(((trifluoromethyl)sulfonyl)oxy)cyclohex-3-ene-1-carboxylate + bis(pinacol)diborane (73183-34-3) → 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-cyclohexene-1-carboxylic acid methyl ester (151075-20-6)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80 - 90 ℃; Inert atmosphere;

Reference yield:

4-carbomethoxycyclohexanone (6297-22-9) → 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-cyclohexene-1-carboxylic acid methyl ester (151075-20-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium hexamethylsilazane / tetrahydrofuran / 2 h / -80 - -70 °C / Inert atmosphere

1.2: 2 h / -80 - -70 °C / Inert atmosphere

2.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 80 - 90 °C / Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; potassium hexamethylsilazane; In tetrahydrofuran; 1,4-dioxane;

Reference yield: 98.0%

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-cyclohexene-1-carboxylic acid methyl ester (151075-20-6) + trans-N,N-dimethyl-N'-(5-bromopyrrolo[2,1-f][1,2,4]triazin-4-yl)-1,4-cyclohexanediamine → methyl 4-(4-(trans-(4-(N,N-dimethylamino)cyclohexyl)amino)pyrrolo[2,1-f][1,2,4]triazin-5-yl)cyclohex-3-enecarboxylate

Guidance literature:

With potassium phosphate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); In 1,4-dioxane; water; at 20 - 80 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.bmc.2018.01.008

upstream raw materials:

bis(pinacol)diborane

4-carbomethoxycyclohexanone

Downstream raw materials:

methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-amino-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)cyclohex-3-enecarboxylate