1-(allyldiphenylsilyl)-2-phenylethyne | 212125-30-9

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 1-(allyldiphenylsilyl)-2-phenylethyne
• 英文别名: Diphenyl-(2-phenylethynyl)-prop-2-enylsilane
• CAS: 212125-30-9
• 化学式: C₂₃H₂₀Si
• 分子量: 324.497
• InChiKey: YFYJHUDIJBVRBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.03
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.04
• 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：

  1-(allyldiphenylsilyl)-2-phenylethyne 、 alkaline earth salt of/the/ methylsulfuric acid 以 甲苯 为溶剂， 反应 2.0h， 生成 2,5-bis(allyldiphenylsilyl)-3,4-diphenylcyclopenta-2,4-dien-1-one 、 2,4-bis(allyldiphenylsilyl)-3,5-diphenylcyclopenta-2,4-dien-1-one
  参考文献：
  名称：

  Direct synthesis of cyclopentadienones by cobalt carbonyl-mediated carbonylative alkyne-alkyne coupling reaction

  摘要：

  Dicobalt carbonyl complex mediates an intermolecular carbonylative coupling reaction between alkynylsilanes, The reaction proceeds under atmospheric pressure of argon and directly provides free cyclopentadienones in high yields (up to 99%). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01175-7
• 作为产物：
  描述：

  二苯基二甲氧基硅烷 在 正丁基锂 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 3.0h， 生成 1-(allyldiphenylsilyl)-2-phenylethyne
  参考文献：
  名称：

  Gold-Catalyzed Intramolecular Allylation of Silyl Alkynes Induced by Silane Alcoholysis

  摘要：

  The activation of alkynyl allyl silanes with a cationic gold catalyst in the presence of alcohols provides vinyl silanes that contain the allyl group at the beta-position and the alkoxysilyl group in cis-orientation. The bond reorganization process is most consistent with the involvement of a carbocationic intermediate, which undergoes a nucleophilic attack by an alcohol selectively at the silicon center. The cis-vinyl silyl ether products can be further elaborated by ring-closing and cross metathesis to form more substituted 1,4-dienyl silanes.

  DOI：

  10.1021/ja062560p

文献信息

• Direct synthesis of cyclopentadienones by cobalt carbonyl-mediated carbonylative alkyne-alkyne coupling reaction
  作者：Takanori Shibata、Toshihiro Ohta、Kenso Soai

  DOI：10.1016/s0040-4039(98)01175-7

  日期：1998.8

  Dicobalt carbonyl complex mediates an intermolecular carbonylative coupling reaction between alkynylsilanes, The reaction proceeds under atmospheric pressure of argon and directly provides free cyclopentadienones in high yields (up to 99%). (C) 1998 Elsevier Science Ltd. All rights reserved.
• Inter- and Intramolecular Carbonylative Alkyne–Alkyne Coupling Reaction Mediated by Cobalt Carbonyl Complex
  作者：Takanori Shibata、Koji Yamashita、Kentaro Takagi、Toshihiro Ohta、Kenso Soai

  DOI：10.1016/s0040-4020(00)00902-9

  日期：2000.11

  Inter- and intramolecular carbonylative coupling reactions proceed between alkynes possessing diphenylallylsilyl group mediated by dicobalt carbonyl complex under argon atmosphere. This coupling reaction directly provides various mono- and bicyclic cyclopentadienones in high yields. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Gold-Catalyzed Intramolecular Allylation of Silyl Alkynes Induced by Silane Alcoholysis
  作者：Sangho Park、Daesung Lee

  DOI：10.1021/ja062560p

  日期：2006.8.1

  The activation of alkynyl allyl silanes with a cationic gold catalyst in the presence of alcohols provides vinyl silanes that contain the allyl group at the beta-position and the alkoxysilyl group in cis-orientation. The bond reorganization process is most consistent with the involvement of a carbocationic intermediate, which undergoes a nucleophilic attack by an alcohol selectively at the silicon center. The cis-vinyl silyl ether products can be further elaborated by ring-closing and cross metathesis to form more substituted 1,4-dienyl silanes.