triphenyl(3-phenylpropanoyl)silane

• 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: triphenyl(3-phenylpropanoyl)silane
• 英文别名: 3-Phenyl-1-triphenylsilylpropan-1-one
• 化学式: C₂₇H₂₄OSi
• 分子量: 392.572
• InChiKey: BXLMSAOFXCSVPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  triphenyl(3-phenylpropanoyl)silane 、 反式-1-碘-1-辛烯 在 四(三苯基膦)钯 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65%的产率得到(Z)-1-phenyl-3-(triphenylsilyloxy)-2,4-undecadiene
  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.