(3-phenethyl-4-phenylbutanoyl)triphenylsilane

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (3-phenethyl-4-phenylbutanoyl)triphenylsilane
• 英文别名: 3-Benzyl-4-phenyl-1-triphenylsilylbutan-1-one
• 化学式: C₃₅H₃₂OSi
• 分子量: 496.724
• InChiKey: ZIXPHFGZCJRUIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.76
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3-phenethyl-4-phenylbutanoyl)triphenylsilane 、 3-氯-2-甲基丙烯 在 copper(I) tert-butoxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以70%的产率得到(Z)-2-methyl-6-phenethyl-7-phenyl-4-(triphenylsilyloxy)-1,4-heptadiene
  参考文献：
  名称：

  Stereoselective Preparation of 1-Siloxy-1-alkenylcopper Species by 1,2-C^sp2-to-O Silyl Migration of Acylsilanes

  摘要：

  1-Siloxy-1-alkenylcopper species were generated by 1,2-Csp2-to-O silyl migration of the copper enolates of acyltriphenylsilanes. The alkenylcopper species reacted with methyl, benzyl, allylic, and tributylstannyl halides to give geometrically pure (Z)-enol silyl ethers. In the presence of Pd(0) catalyst, the cross-coupling of the alkenyl copper species with aryl and alkenyl iodides also proceeded to give the (Z)-enol silyl ethers with high stereoselectivity.

  DOI：

  10.1021/ja0658822

文献信息

• Stereoselective Preparation of 1-Siloxy-1-alkenylcopper Species by 1,2-C^sp2-to-O Silyl Migration of Acylsilanes
  作者：Akira Tsubouchi、Kotaro Onishi、Takeshi Takeda

  DOI：10.1021/ja0658822

  日期：2006.11.1

  1-Siloxy-1-alkenylcopper species were generated by 1,2-Csp2-to-O silyl migration of the copper enolates of acyltriphenylsilanes. The alkenylcopper species reacted with methyl, benzyl, allylic, and tributylstannyl halides to give geometrically pure (Z)-enol silyl ethers. In the presence of Pd(0) catalyst, the cross-coupling of the alkenyl copper species with aryl and alkenyl iodides also proceeded to give the (Z)-enol silyl ethers with high stereoselectivity.