Allyl-oct-1-ynyl-diphenyl-silane | 909805-45-4

• 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: Allyl-oct-1-ynyl-diphenyl-silane
• 英文别名: Oct-1-ynyl-diphenyl-prop-2-enylsilane；oct-1-ynyl-diphenyl-prop-2-enylsilane
• CAS: 909805-45-4
• 化学式: C₂₃H₂₈Si
• 分子量: 332.561
• InChiKey: AUXOIRCOSRRGLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.95
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  Allyl-oct-1-ynyl-diphenyl-silane 、 4-戊烯-2-醇 在 silver hexafluoroantimonate 、 三苯基膦氯金 作用下， 以 二氯甲烷 为溶剂， 以71%的产率得到
  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
• 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 Allyl-oct-1-ynyl-diphenyl-silane
  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

• 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.