4-(tert-butyl-dimethyl-silanyloxy)-4-naphthalen-1-yl-1-phenyl-but-2-yn-1-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(tert-butyl-dimethyl-silanyloxy)-4-naphthalen-1-yl-1-phenyl-but-2-yn-1-one
• 英文别名: 4-[Tert-butyl(dimethyl)silyl]oxy-4-naphthalen-1-yl-1-phenylbut-2-yn-1-one
• 化学式: C₂₆H₂₈O₂Si
• 分子量: 400.593
• InChiKey: YARPNYHBPZVCDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.79
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-甲基-N-甲基苯甲酰胺 、 Tert-butyl-dimethyl-(1-naphthalen-1-ylprop-2-ynoxy)silane 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 以60%的产率得到4-(tert-butyl-dimethyl-silanyloxy)-4-naphthalen-1-yl-1-phenyl-but-2-yn-1-one
  参考文献：
  名称：

  Highly Stereoselective Addition of Stannylcuprates to Alkynones

  摘要：

  The addition of stannylcuprate reagents such as (Bu3Sn)(PhS)CuLi to alkynones has been found to proceed in high yield and with excellent stereoselectivity for the Z isomer of the product (>95%). The behavior of the stannylcuprates is thus very different from that of their "carbocuprate" counterparts such as Me2CuLi or Me2Cu(CN)Li-2 which are nonstereoselective. Furthermore, in contrast to the reactions of (R3Sn)(PhS)CuLi with the corresponding alkynoates, the presence of a proton source in the reaction medium has no effect on the stereos electivity of the reaction of alkynones.

  DOI：

  10.1021/jo0259008

文献信息

• Highly Stereoselective Addition of Stannylcuprates to Alkynones
  作者：Thomas E. Nielsen、Maria A. Cubillo de Dios、David Tanner

  DOI：10.1021/jo0259008

  日期：2002.10.1

  The addition of stannylcuprate reagents such as (Bu3Sn)(PhS)CuLi to alkynones has been found to proceed in high yield and with excellent stereoselectivity for the Z isomer of the product (>95%). The behavior of the stannylcuprates is thus very different from that of their "carbocuprate" counterparts such as Me2CuLi or Me2Cu(CN)Li-2 which are nonstereoselective. Furthermore, in contrast to the reactions of (R3Sn)(PhS)CuLi with the corresponding alkynoates, the presence of a proton source in the reaction medium has no effect on the stereos electivity of the reaction of alkynones.