trans-5,5-Dimethyl-1-trimethylsilylhex-2-en | 41825-92-7

• 分子结构分类: 有机化合物 - 有机盐 - 有机金属盐
• 英文名称: trans-5,5-Dimethyl-1-trimethylsilylhex-2-en
• 英文别名: 1-Trimethylsilyl-5,5-dimethylhexen-(2)；[(E)-5,5-dimethylhex-2-enyl]-trimethylsilane
• CAS: 41825-92-7
• 化学式: C₁₁H₂₄Si
• 分子量: 184.397
• InChiKey: DFINJUQXYZCAGQ-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.32
• 重原子数：
  12.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  六甲基二硅烷 、 三甲基乙酰氯 、 1,3-丁二烯 在 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 trans-5,5-Dimethyl-1-trimethylsilylhex-2-en 、 2,2-dimethyl-7-(trimethylsilyl)-5-hepten-3-one
  参考文献：
  名称：

  1,4-Carbosilylation of 1,3-Dienes via Palladium Catalyzed Three-Component Coupling Reaction

  摘要：

  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.

  DOI：

  10.1021/ja00144a005

文献信息

• CUNICO R. F.; HAN Y., J. ORGANOMETAL. CHEM., 1979, 174, NO 3, 247-262
  作者：CUNICO R. F.、 HAN Y.

  DOI：——

  日期：——