(Z)-1-(tert-butyldimethylsilyloxy)-4-bromo-7-phenyl-4-heptene-2,6-diyne

Base Information

Chemical Name:(Z)-1-(tert-butyldimethylsilyloxy)-4-bromo-7-phenyl-4-heptene-2,6-diyne
CAS No.:919087-41-5
Molecular Formula:C₁₉H₂₃BrOSi
Molecular Weight:375.381
Hs Code.:

Synonyms:(Z)-1-(tert-butyldimethylsilyloxy)-4-bromo-7-phenyl-4-heptene-2,6-diyne

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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 (Z)-1-(tert-butyldimethylsilyloxy)-4-bromo-7-phenyl-4-heptene-2,6-diyne

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Technology Process of (Z)-1-(tert-butyldimethylsilyloxy)-4-bromo-7-phenyl-4-heptene-2,6-diyne

There total 3 articles about (Z)-1-(tert-butyldimethylsilyloxy)-4-bromo-7-phenyl-4-heptene-2,6-diyne 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: 71.0%

: 76782-82-6
tert-Butyldimethyl(prop-2-ynyloxy)silane

: 181214-43-7
(4,4-dibromobut-3-en-1-ynyl)benzene

: 919087-41-5
(Z)-1-(tert-butyldimethylsilyloxy)-4-bromo-7-phenyl-4-heptene-2,6-diyne

Guidance literature:: tert-Butyldimethyl(prop-2-ynyloxy)silane; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

With zinc dibromide; In tetrahydrofuran; hexane; at -78 - 25 ℃;

(4,4-dibromobut-3-en-1-ynyl)benzene; dichloro[bis(2-(diphenylphosphino)phenyl)ether]palladium(ll); In tetrahydrofuran; hexane; at 0 ℃; for 8h;
DOI:10.1021/ol0623825

Reference yield:

: 2579-22-8
Phenylpropargyl aldehyde

: 919087-41-5
(Z)-1-(tert-butyldimethylsilyloxy)-4-bromo-7-phenyl-4-heptene-2,6-diyne

Guidance literature:: Multi-step reaction with 2 steps

1.1: 6.86 g / PPH₃; 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: ZnBr₂ / tetrahydrofuran; hexane / -78 - 25 °C

2.3: 71 percent / Pd(DPEphos)Cl₂ / tetrahydrofuran; hexane / 8 h / 0 °C

With 2,6-dimethylpyridine; n-butyllithium; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ol0623825

Reference yield:

: 536-74-3
phenylacetylene

: 919087-41-5
(Z)-1-(tert-butyldimethylsilyloxy)-4-bromo-7-phenyl-4-heptene-2,6-diyne

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: tetrahydrofuran; hexane / -78 - 23 °C

2.1: 6.86 g / PPH₃; 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

3.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

3.2: ZnBr₂ / tetrahydrofuran; hexane / -78 - 25 °C

3.3: 71 percent / Pd(DPEphos)Cl₂ / tetrahydrofuran; hexane / 8 h / 0 °C

With 2,6-dimethylpyridine; n-butyllithium; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ol0623825