benzyl N-[(3S)-3-[[(R)-tert-butylsulfinyl]amino]-6-trimethylsilylhex-5-ynyl]carbamate | 1208066-46-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl N-[(3S)-3-[[(R)-tert-butylsulfinyl]amino]-6-trimethylsilylhex-5-ynyl]carbamate
• CAS: 1208066-46-9
• 化学式: C₂₁H₃₄N₂O₃SSi
• 分子量: 422.664
• InChiKey: AMXVCGRREONMAZ-UZTOHYMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  86.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  trimethyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-1-yn-1-yl)silane 、 在 diethylzinc 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 5.0h， 以86%的产率得到benzyl N-[(3S)-3-[[(R)-tert-butylsulfinyl]amino]-6-trimethylsilylhex-5-ynyl]carbamate
  参考文献：
  名称：

  Highly Diastereoselective Zinc-Catalyzed Propargylation of tert-Butanesulfinyl Imines

  摘要：

  A zinc-catalyzed diastereoselective propargylation of t-butanesulfinyl imines is presented. The methodology provided both aliphatic and aryl homopropargylic amines in up to 98:2 and 99.8:0.2 dr, respectively. The utility of the homopropargylic amines was demonstrated by the application to the synthesis of a cis-substituted pyrido-indole through a diastereoselective Pictet-Spengler cyclization.

  DOI：

  10.1021/ol9028258

文献信息

• Highly Diastereoselective Zinc-Catalyzed Propargylation of <i>tert-</i>Butanesulfinyl Imines
  作者：Daniel R. Fandrick、Courtney S. Johnson、Keith R. Fandrick、Jonathan T. Reeves、Zhulin Tan、Heewon Lee、Jinhua J. Song、Nathan K. Yee、Chris H. Senanayake

  DOI：10.1021/ol9028258

  日期：2010.2.19

  A zinc-catalyzed diastereoselective propargylation of t-butanesulfinyl imines is presented. The methodology provided both aliphatic and aryl homopropargylic amines in up to 98:2 and 99.8:0.2 dr, respectively. The utility of the homopropargylic amines was demonstrated by the application to the synthesis of a cis-substituted pyrido-indole through a diastereoselective Pictet-Spengler cyclization.