3-(diethylsilyl)-1,2,3,4-tetrahydroquinoline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-(diethylsilyl)-1,2,3,4-tetrahydroquinoline
• 英文别名: Diethyl(1,2,3,4-tetrahydroquinolin-3-yl)silane；diethyl(1,2,3,4-tetrahydroquinolin-3-yl)silane
• 化学式: C₁₃H₂₁NSi
• 分子量: 219.402
• InChiKey: KVHVTEVKJMMZDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.29
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  喹啉 、 二乙基硅烷 在 三(五氟苯基)硼烷 作用下， 以 氘代氯仿 为溶剂， 反应 6.0h， 以93%的产率得到3-(diethylsilyl)-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  Boron-Catalyzed Silylative Reduction of Quinolines: Selective sp³ C–Si Bond Formation

  摘要：

  A silylative reduction of quinolines to synthetically versatile tetrahydroquinoline molecules involving the formation of a C(sp(3)-Si bond exclusively beta to nitrogen is described. Triarylborane is a highly efficient catalyst (up to 1000 turnovers), and silanes serve as both a silyl source and a reducing reagent. The present procedure is convenient to perform even on a large scale with excellent stereoselectivity. Mechanistic studies revealed that the formation of a 1,4-addition adduct is rate-limiting while the subsequent C(sp(3-)Si bond-forming step from the 1,4-adduct is facile.

  DOI：

  10.1021/ja510674u

文献信息

• Boron-Catalyzed Silylative Reduction of Quinolines: Selective sp³ C–Si Bond Formation
  作者：Narasimhulu Gandhamsetty、Seewon Joung、Sung-Woo Park、Sehoon Park、Sukbok Chang

  DOI：10.1021/ja510674u

  日期：2014.12.3

  A silylative reduction of quinolines to synthetically versatile tetrahydroquinoline molecules involving the formation of a C(sp(3)-Si bond exclusively beta to nitrogen is described. Triarylborane is a highly efficient catalyst (up to 1000 turnovers), and silanes serve as both a silyl source and a reducing reagent. The present procedure is convenient to perform even on a large scale with excellent stereoselectivity. Mechanistic studies revealed that the formation of a 1,4-addition adduct is rate-limiting while the subsequent C(sp(3-)Si bond-forming step from the 1,4-adduct is facile.