(Z)-2-bromo-5-phenyl-1-trimethylsilyl-2-pentene | 683773-78-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-2-bromo-5-phenyl-1-trimethylsilyl-2-pentene
• 英文别名: 2-bromo-5-phenyl-1-trimethylsilyl-2-pentene；[(Z)-2-bromo-5-phenylpent-2-enyl]-trimethylsilane
• CAS: 683773-78-6
• 化学式: C₁₄H₂₁BrSi
• 分子量: 297.31
• InChiKey: CSVHWEYHQNGOBF-KAMYIIQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.24
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (Z)-2-bromo-5-phenyl-1-trimethylsilyl-2-pentene 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到(4-bromopent-4-en-1-yl)benzene
  参考文献：
  名称：

  Preparation of 2-trimethylsilylmethyl-1-alkene; cross-coupling and protodesilylation sequence from 1,1-dibromo-1-alkene

  摘要：

  A new method for the preparation of exomethylene type allylsilane is described. Selective mono-protodesilylation of 1-trimethylsityl-2-trimethylsilylmethyl-2-alkenes 2 with PPTS afforded 2-trimethylsilylmethyl-l-alkeiles 4 in excellent yields. Since the resulting allylsilanes 4 possess an exomethylene unit, the reactions of 4 with carbonyl compounds in the presence of Lewis acids gave the corresponding product 7 having an exomethylene unit in excellent yields. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.12.044
• 作为产物：
  描述：

  (三甲基硅基)甲基氯化镁 、 4-phenyl-1,1-dibromo-1-butene 在 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) 作用下， 以 乙醚 为溶剂， 以89%的产率得到(Z)-2-bromo-5-phenyl-1-trimethylsilyl-2-pentene
  参考文献：
  名称：

  Synthesis and Reaction of Bromoallylsilane: A Short Access to β,γ-Disubstituted α-Methylene-γ-butyrolactone

  摘要：

  (Z)-beta-Bromoallylsilanes (1a-c) were prepared by a stereoselective Ni-catalyzed cross-coupling reaction of 1,1-dibromo-4-phenylbutene (4) with silylmethylmagnesium halide. Sakurai-Hosomi reaction of la with aldehyde gave syn-3-alkyl-2-bromo-4-hydroxyalkene (2a, 2c, and 2c) and that with acetal gave syn-4-alkoxy-3-alkyl-2-bromoalkene (2b and 2d) stereoselectively. The products with formyl function reacted with a Ni-carbonyl complex to give beta,gamma-disubstituted (alpha-methylene-gamma-butyrolactones (3) in good yields. Pd-catalyzed cross-coupling reaction of la-c or 4 with silylmethylmagnesium halide gave 1, 1-bis(silylmethyl)-1-alkenes (1d-i), which reacted with dimethyl acetal to generate more functionalized allylsilane (6).

  DOI：

  10.3987/com-03-s52

文献信息

• Nucleophilic substitution at an sp2 carbon of vinyl halides with an intramolecular thiolate moiety: synthesis of 2-alkylidenethietanes
  作者：Mao-Yi Lei、Koji Fukamizu、Yong-Jun Xiao、Wei-Min Liu、Scott Twiddy、Shunsuke Chiba、Kaori Ando、Koichi Narasaka

  DOI：10.1016/j.tetlet.2008.04.127

  日期：2008.6

  Various 2-alkylidenethietanes were synthesized by intramolecular nucleophilic substitution reactions at an sp2 carbon of vinyl halides with thiolate moieties. The reaction pathway of the substitution reactions was confirmed as a very rare SNVπ mechanism by theoretical and experimental studies.

  通过分子内的亲核取代反应，在卤代乙烯的sp 2碳上具有硫醇盐部分，合成了各种2-烷基亚乙基庚烷。的取代反应的反应路径被确认为一种非常罕见的小号Ñ通过理论和实验研究Vπ机制。
• Nucleophilic substitution reaction at an sp2 carbon of vinyl halides with an intramolecular thiol moiety: synthesis of thio-heterocycles
  作者：Mao-Yi Lei、Yong-Jun Xiao、Wei-Min Liu、Koji Fukamizu、Shunsuke Chiba、Kaori Ando、Koichi Narasaka

  DOI：10.1016/j.tet.2009.06.078

  日期：2009.8

  This article presents a full account of intramolecular vinylic substitution reactions of bromoalkenes having an acetylthio moiety, which give sulfur-containing heterocycles such as dihydrothiophene, tetrahydrothiopyran, and 2-alkylidenethietane derivatives. The reaction pathways of the substitution reactions were investigated by theoretical and experimental studies.

  本文全面介绍了具有乙酰硫基部分的溴代烯烃的分子内乙烯基取代反应，该反应可生成含硫杂环，如二氢噻吩，四氢噻喃和2-烷基亚乙基庚烷衍生物。通过理论和实验研究了取代反应的反应途径。
• Preparation of 2-trimethylsilylmethyl-1-alkene; cross-coupling and protodesilylation sequence from 1,1-dibromo-1-alkene
  作者：Jun’ichi Uenishi、Takuya Iwamoto、Masashi Ohmi

  DOI：10.1016/j.tetlet.2006.12.044

  日期：2007.2

  A new method for the preparation of exomethylene type allylsilane is described. Selective mono-protodesilylation of 1-trimethylsityl-2-trimethylsilylmethyl-2-alkenes 2 with PPTS afforded 2-trimethylsilylmethyl-l-alkeiles 4 in excellent yields. Since the resulting allylsilanes 4 possess an exomethylene unit, the reactions of 4 with carbonyl compounds in the presence of Lewis acids gave the corresponding product 7 having an exomethylene unit in excellent yields. (c) 2007 Elsevier Ltd. All rights reserved.
• Synthesis and Reaction of Bromoallylsilane: A Short Access to β,γ-Disubstituted α-Methylene-γ-butyrolactone
  作者：Jun'ichi Uenishi、Masashi Ohmi

  DOI：10.3987/com-03-s52

  日期：——

  (Z)-beta-Bromoallylsilanes (1a-c) were prepared by a stereoselective Ni-catalyzed cross-coupling reaction of 1,1-dibromo-4-phenylbutene (4) with silylmethylmagnesium halide. Sakurai-Hosomi reaction of la with aldehyde gave syn-3-alkyl-2-bromo-4-hydroxyalkene (2a, 2c, and 2c) and that with acetal gave syn-4-alkoxy-3-alkyl-2-bromoalkene (2b and 2d) stereoselectively. The products with formyl function reacted with a Ni-carbonyl complex to give beta,gamma-disubstituted (alpha-methylene-gamma-butyrolactones (3) in good yields. Pd-catalyzed cross-coupling reaction of la-c or 4 with silylmethylmagnesium halide gave 1, 1-bis(silylmethyl)-1-alkenes (1d-i), which reacted with dimethyl acetal to generate more functionalized allylsilane (6).