N,N-dimethyl-2-(4-(2-phenyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)but-1-en-1-yl)phenoxy)ethanamine

Base Information

• Chemical Name: N,N-dimethyl-2-(4-(2-phenyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)but-1-en-1-yl)phenoxy)ethanamine
• CAS No.: 1370699-81-2
• Molecular Formula: C₃₂H₄₀BNO₃
• Molecular Weight: 497.485
• Mol file: 1370699-81-2.mol

Synonyms:N,N-dimethyl-2-(4-(2-phenyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)but-1-en-1-yl)phenoxy)ethanamine

Chemical Property of N,N-dimethyl-2-(4-(2-phenyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)but-1-en-1-yl)phenoxy)ethanamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N,N-dimethyl-2-(4-(2-phenyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)but-1-en-1-yl)phenoxy)ethanamine

There total 6 articles about N,N-dimethyl-2-(4-(2-phenyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)but-1-en-1-yl)phenoxy)ethanamine 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: 90.0%

(E,Z)-4-(1-{4-[2-(dimethylamino)ethoxy]phenyl}-2-phenylbut-1-en-1-yl)phenyl trifluoromethanesulfonate (1370699-80-1) + bis(pinacol)diborane (73183-34-3) → N,N-dimethyl-2-(4-(2-phenyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)but-1-en-1-yl)phenoxy)ethanamine (1370699-81-2)

Guidance literature:

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

DOI:10.1021/ml3000287

Reference yield:

4,4'-Dihydroxybenzophenone (611-99-4) → N,N-dimethyl-2-(4-(2-phenyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)but-1-en-1-yl)phenoxy)ethanamine (1370699-81-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: titanium tetrachloride; zinc / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere; Reflux; Darkness

2.1: caesium carbonate / N,N-dimethyl-formamide / 0.17 h / 70 - 80 °C

2.2: 1.75 h

3.1: pyridine / dichloromethane / 1 h / 0 - 20 °C

4.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 80 °C / Inert atmosphere

With pyridine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; titanium tetrachloride; caesium carbonate; zinc; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; 1.1: McMurry reaction;

DOI:10.1021/ml3000287

Reference yield:

1-phenyl-propan-1-one (93-55-0) → N,N-dimethyl-2-(4-(2-phenyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)but-1-en-1-yl)phenoxy)ethanamine (1370699-81-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: titanium tetrachloride; zinc / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere; Reflux; Darkness

2.1: caesium carbonate / N,N-dimethyl-formamide / 0.17 h / 70 - 80 °C

2.2: 1.75 h

3.1: pyridine / dichloromethane / 1 h / 0 - 20 °C

4.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 80 °C / Inert atmosphere

With pyridine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; titanium tetrachloride; caesium carbonate; zinc; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; 1.1: McMurry reaction;

DOI:10.1021/ml3000287

upstream raw materials:

(E,Z)-4-(1-{4-[2-(dimethylamino)ethoxy]phenyl}-2-phenylbut-1-en-1-yl)phenyl trifluoromethanesulfonate

bis(pinacol)diborane

4,4'-Dihydroxybenzophenone

1,1-bis(4-hydroxyphenyl)-2-phenyl-1-butene

Downstream raw materials:

potassium [4-(1-{4-[2-(dimethylamino)ethoxy]phenyl}-2-phenylbut-1-en-1-yl)phenyl]trifluoroboranuide

(4-(1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenylbut-1-en-1-yl)phenyl)boronic acid

Refernces

• 1、 Jiang, Quan,Zhong, Qiu,Zhang, Qiang,Zheng, Shilong,Wang, Guangdi. "Boron-based 4-hydroxytamoxifen bioisosteres for treatment of de novo tamoxifen resistant breast cancer". supporting information; experimental part. p. 392 - 396. Retrieved 2012/07/13.