(3E)-4-[3'-(1-adamantyl)-4'-benzyloxy-2-chloro-4-biphenyl]but-3-en-2-one

Base Information

Chemical Name:(3E)-4-[3'-(1-adamantyl)-4'-benzyloxy-2-chloro-4-biphenyl]but-3-en-2-one
CAS No.:943141-79-5
Molecular Formula:C₃₃H₃₃ClO₂
Molecular Weight:497.077
Hs Code.:

Synonyms:(3E)-4-[3'-(1-adamantyl)-4'-benzyloxy-2-chloro-4-biphenyl]but-3-en-2-one

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3E)-4-[3'-(1-adamantyl)-4'-benzyloxy-2-chloro-4-biphenyl]but-3-en-2-one

Chemical Property:

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Technology Process of (3E)-4-[3'-(1-adamantyl)-4'-benzyloxy-2-chloro-4-biphenyl]but-3-en-2-one

There total 8 articles about (3E)-4-[3'-(1-adamantyl)-4'-benzyloxy-2-chloro-4-biphenyl]but-3-en-2-one 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: 38.0%

: 943141-66-0
4-[3'-(1-adamantyl)-4'-benzyloxyphenyl]-3-chlorobenzaldehyde

: 2236-01-3
acetonyltriphenylphosphonium bromide

: 943141-79-5
(3E)-4-[3'-(1-adamantyl)-4'-benzyloxy-2-chloro-4-biphenyl]but-3-en-2-one

Guidance literature:: With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; In tetrahydrofuran; at 20 - 70 ℃; for 25h;
DOI:10.1021/jm0613323

Reference yield:

: 736992-49-7
2-(1-adamantyl)-1-benzyloxy-4-bromobenzene

: 943141-79-5
(3E)-4-[3'-(1-adamantyl)-4'-benzyloxy-2-chloro-4-biphenyl]but-3-en-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -78 °C

1.2: tri(isopropyl)borate / tetrahydrofuran; hexane / -78 - 20 °C

1.3: 89 percent / aq. HCl / tetrahydrofuran; hexane

2.1: 78 percent / LiCl; aq. Na₂CO₃ / tetrakis(triphenylphosphine)palladium / 1,2-dimethoxy-ethane / 24 h / Heating

3.1: 38 percent / 1,5,7-triazabicyclo[4.4.0]dec-5-ene / tetrahydrofuran / 25 h / 20 - 70 °C

With n-butyllithium; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; sodium carbonate; lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; 2.1: Suzuki-Miyaura coupling;
DOI:10.1021/jm0613323

Reference yield:

: 106-41-2
4-bromo-phenol

: 943141-79-5
(3E)-4-[3'-(1-adamantyl)-4'-benzyloxy-2-chloro-4-biphenyl]but-3-en-2-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: conc. sulfuric acid / CH₂Cl₂

2.1: K₂CO₃ / acetone / Heating

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -78 °C

3.2: tri(isopropyl)borate / tetrahydrofuran; hexane / -78 - 20 °C

3.3: 89 percent / aq. HCl / tetrahydrofuran; hexane

4.1: 78 percent / LiCl; aq. Na₂CO₃ / tetrakis(triphenylphosphine)palladium / 1,2-dimethoxy-ethane / 24 h / Heating

5.1: 38 percent / 1,5,7-triazabicyclo[4.4.0]dec-5-ene / tetrahydrofuran / 25 h / 20 - 70 °C

With n-butyllithium; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; sodium carbonate; potassium carbonate; lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sulfuric acid; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; dichloromethane; acetone; 1.1: Friedel-Crafts alkylation / 4.1: Suzuki-Miyaura coupling;
DOI:10.1021/jm0613323