[(16E)-16-(3-carbamoylbenzylidene)-17-oxoestra-1⁽¹⁰⁾,2,4-trien-3-yl]boronic acid

Base Information

• Chemical Name: [(16E)-16-(3-carbamoylbenzylidene)-17-oxoestra-1⁽¹⁰⁾,2,4-trien-3-yl]boronic acid
• CAS No.: 1401938-22-4
• Molecular Formula: C₂₆H₂₈BNO₄
• Molecular Weight: 429.324

Synonyms:[(16E)-16-(3-carbamoylbenzylidene)-17-oxoestra-1⁽¹⁰⁾,2,4-trien-3-yl]boronic acid

Chemical Property of [(16E)-16-(3-carbamoylbenzylidene)-17-oxoestra-1⁽¹⁰⁾,2,4-trien-3-yl]boronic acid

Chemical Property:

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Technology Process of [(16E)-16-(3-carbamoylbenzylidene)-17-oxoestra-1⁽¹⁰⁾,2,4-trien-3-yl]boronic acid

There total 2 articles about [(16E)-16-(3-carbamoylbenzylidene)-17-oxoestra-1⁽¹⁰⁾,2,4-trien-3-yl]boronic acid 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: 10.0%

(3aS,3bR,9bS,11aS)‐11a‐methyl‐7‐(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)‐1H,2H,3H,3aH,3bH,4H,5H,9bH,10H,11H,11aH‐cyclopenta[a]phenanthren‐1‐one + 3-carboxamidobenzaldehyde (126534-87-0) → [(16E)-16-(3-carbamoylbenzylidene)-17-oxoestra-1(10),2,4-trien-3-yl]boronic acid (1401938-22-4)

Guidance literature:

(3aS,3bR,9bS,11aS)‐11a‐methyl‐7‐(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)‐1H,2H,3H,3aH,3bH,4H,5H,9bH,10H,11H,11aH‐cyclopenta[a]phenanthren‐1‐one; 3-carboxamidobenzaldehyde; With potassium hydroxide; In ethanol; water; for 0.5h; Reflux;

With hydrogenchloride; In ethanol; water;

Reference yield:

estrone triflate (92817-04-4) → [(16E)-16-(3-carbamoylbenzylidene)-17-oxoestra-1(10),2,4-trien-3-yl]boronic acid (1401938-22-4)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / 1,4-dioxane / 24 h / 100 °C / Inert atmosphere

2: potassium hydroxide / ethanol; water / 0.5 h / Reflux

With triethylamine; potassium hydroxide; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); In 1,4-dioxane; ethanol; water;

Reference yield:

[(16E)-16-(3-carbamoylbenzylidene)-17-oxoestra-1(10),2,4-trien-3-yl]boronic acid (1401938-22-4) → [(16β,17β)-16-(3-carbamoylbenzyl)-17-hydroxyestra-1(10),2,4-trien-3-yl]boronic acid (1401937-82-3)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium tetrahydroborate; methanol / 1 h / 20 °C

2: hydrogen / palladium 10% on activated carbon / ethanol / 24 h / 20 °C / Inert atmosphere

With methanol; sodium tetrahydroborate; hydrogen; palladium 10% on activated carbon; In ethanol;

upstream raw materials:

estrone triflate

3-carboxamidobenzaldehyde

Downstream raw materials:

[(16β,17β)-16-(3-carbamoylbenzyl)-17-hydroxyestra-1(10),2,4-trien-3-yl]boronic acid

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