(E)-2-methyl-4-phenyl-1-trimethylsilylbut-2-ene | 79158-61-5

• 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: (E)-2-methyl-4-phenyl-1-trimethylsilylbut-2-ene
• 英文别名: trimethyl-[(Z)-2-methyl-4-phenylbut-2-enyl]silane
• CAS: 79158-61-5
• 化学式: C₁₄H₂₂Si
• 分子量: 218.414
• InChiKey: XXJQTUOWLAHVST-RAXLEYEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.51
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为产物：
  描述：

  3-(三甲基甲硅烷基甲基)丁-3-烯酸 在 lithium diisopropyl amide 作用下， 以 xylene 为溶剂， 反应 6.0h， 生成 (E)-2-methyl-4-phenyl-1-trimethylsilylbut-2-ene
  参考文献：
  名称：

  3-三甲基甲硅烷基甲基二烯酸酯的区域和立体选择性烷基化。3-烷基化的2-甲基烯丙基硅烷的新型合成

  摘要：

  从容易获得的3-三甲基甲硅烷基甲基-3-丁烯酸及其甲酯得到的3-三甲基甲硅烷基甲基二烯酸锂和铜阴离子进行区域选择性和立体选择性烷基化。通过热解，α-烷基化产物易于转化为3-烷基化2-甲基烯丙基硅烷。

  DOI：

  10.1016/s0040-4039(01)90413-7

文献信息

• Mills, Nancy S.; Ruud, C. Channing, Journal of the Chemical Society. Perkin transactions II, 1996, # 9, p. 2035 - 2040
  作者：Mills, Nancy S.、Ruud, C. Channing

  DOI：——

  日期：——
• 1,4-Carbosilylation of 1,3-Dienes via Palladium Catalyzed Three-Component Coupling Reaction
  作者：Yasushi Obora、Yasushi Tsuji、Takashi Kawamura

  DOI：10.1021/ja00144a005

  日期：1995.10

  Three-component coupling reaction of acid chlorides, organodisilanes, and 1,3-dienes achieves 1,4-carbosilylation of the 1,3-dienes to afford allylic silanes as the product. Bis(dibenzylideneacetone)palladium, a naked Pd(0) complex without donating ligand, showed high catalytic activity. A carbon and a silicon substituent are introduced at 1- and 4-positions of the 1,3-dienes regio- and stereoselectively with concomitant decarbonylation of the acid chlorides. A wide variety of allylic silanes are synthesized in high yields from these easily accessible substrates. On the other hand, a bully acid chloride such as adamantane-1-carboxylic acid chloride did not undergo the decarbonylation reaction but afforded allylic silanes containing acyl functionality. In all these reactions, transmetalation of the disilanes with eta(3)-allylchloropalladium intermediates might be a critical step in the catalytic cycle. As a model reaction for the transmetalation, reaction of di-mu-chlorobis[(1,2,3-eta)-4-phenyl-2-butenyl]dipalladium with disilanes was carried out. Although intermediate eta(3)-allylsilylpalladium species could not be detected, the corresponding allylic silanes, silyl chlorides, and Pd(0) metal were formed during the reaction. Furthermore, a similar three-component coupling reaction using aryl iodides, organosilylstannanes, and dienes also proceeded. However, the selectivity and the yield decreased considerably.
• NISHIYAMA HISAO; ITAGAKI KAZUYOSHI; TAKAHASHI KAORU; ITOH KENJI, TETRAHEDRON LETT., 1981, 22, NO 18, 1691-1694
  作者：NISHIYAMA HISAO、 ITAGAKI KAZUYOSHI、 TAKAHASHI KAORU、 ITOH KENJI

  DOI：——

  日期：——
• Regio- and stereo-selective alkylation of 3-trimethylsilylmethyl dienolates. A novel synthesis of 3-alkylated 2-methallylsilanes
  作者：Hisao Nishiyama、Kazuyoshi Itagaki、Kaoru Takahashi、Kenji Itoh

  DOI：10.1016/s0040-4039(01)90413-7

  日期：1981.1

  Lithium and copper 3-trimethylsilylmethyl dienolate anions derived from easily available 3-trimethylsilylmethyl-3-butenoic acid and its methyl ester underwent regio- and stereo-selective alkylation. α-Alkylated products were readily transformed to 3-alkylated 2-methallylsilanes by pyrolysis.

  从容易获得的3-三甲基甲硅烷基甲基-3-丁烯酸及其甲酯得到的3-三甲基甲硅烷基甲基二烯酸锂和铜阴离子进行区域选择性和立体选择性烷基化。通过热解，α-烷基化产物易于转化为3-烷基化2-甲基烯丙基硅烷。