2-(trimethylsilyl)ethyl (3R,4S)-4-(2-oxoethyl)-3-vinylpiperidine-1-carboxylate | 865853-23-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 2-(trimethylsilyl)ethyl (3R,4S)-4-(2-oxoethyl)-3-vinylpiperidine-1-carboxylate
• 英文别名: 2-trimethylsilylethyl (3R,4S)-3-ethenyl-4-(2-oxoethyl)piperidine-1-carboxylate
• CAS: 865853-23-2
• 化学式: C₁₅H₂₇NO₃Si
• 分子量: 297.47
• InChiKey: PMWGXOBGFSGKBX-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.17
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl (3R,4S)-4-(2-oxoethyl)-3-vinylpiperidine-1-carboxylate 在 AD-mix-β 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 2-trimethylsilylethyl (3R,4S)-4-[(2R,3R)-2,3-dihydroxy-3-(6-methoxyquinolin-4-yl)propyl]-3-ethenylpiperidine-1-carboxylate
  参考文献：
  名称：

  Improved synthesis of quinine alkaloids with the Teoc protective group

  摘要：

  TeocCl (Teoc: C(=O)O(CH2)(2)TMS) generated in situ was conveniently used for trans-protection of the N-Bn piperidine intermediate to N-Teoc piperidine. Later, deprotection of the Teoc group and the subsequent quinuclidine ring formation was achieved with CsF in a domino fashion to afford the quinine alkaloids. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.171
• 作为产物：
  描述：

  (3R,4S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-vinyl-piperidine-1-carboxylic acid 2-trimethylsilanyl-ethyl ester 在 盐酸 、 pyridinium chlorochromate 作用下， 以 甲醇 为溶剂， 生成 2-(trimethylsilyl)ethyl (3R,4S)-4-(2-oxoethyl)-3-vinylpiperidine-1-carboxylate
  参考文献：
  名称：

  Improved synthesis of quinine alkaloids with the Teoc protective group

  摘要：

  TeocCl (Teoc: C(=O)O(CH2)(2)TMS) generated in situ was conveniently used for trans-protection of the N-Bn piperidine intermediate to N-Teoc piperidine. Later, deprotection of the Teoc group and the subsequent quinuclidine ring formation was achieved with CsF in a domino fashion to afford the quinine alkaloids. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.171

文献信息

• Practical and Highly Selective Sulfur Ylide Mediated Asymmetric Epoxidations and Aziridinations Using an Inexpensive, Readily Available Chiral Sulfide. Applications to the Synthesis of Quinine and Quinidine
  作者：Ona Illa、Muhammad Arshad、Abel Ros、Eoghan M. McGarrigle、Varinder K. Aggarwal

  DOI：10.1021/ja9100276

  日期：2010.2.17

  one-step synthesis of a chiral sulfide which exhibits outstanding selectivities in sulfur ylide mediated asymmetric epoxidations and aziridinations. In particular reactions of benzyl and allylic sulfonium salts with both aromatic and aliphatic aldehydes gave epoxides with perfect enantioselectivities and the highest diastereoselectivities reported to date. In addition reactions with imines gave aziridines

  用最容易获得的同手性分子之一（柠檬烯）加热一种最丰富的天然无机化学物质（元素硫），可以一步合成手性硫化物，该硫化物在硫叶立德介导的不对称环氧化和氮丙啶化反应中表现出出色的选择性。特别是苄基和烯丙基锍盐与芳香族和脂肪族醛的反应产生具有完美对映选择性和迄今为止报道的最高非对映选择性的环氧化物。此外，与亚胺的反应再次得到具有迄今为止报道的最高对映选择性和非对映选择性的氮丙啶。该反应是可扩展的，并且硫化物可以高产率地重新分离。
• Synthesis of quinine and quinidine using sulfur ylide-mediated asymmetric epoxidation as a key step
  作者：Muhammad Arshad、M. Alejandro Fernández、Eoghan M. McGarrigle、Varinder K. Aggarwal

  DOI：10.1016/j.tetasy.2010.04.046

  日期：2010.7

  The epoxidation of meroquinene aldehyde with a chiral sulfur ylide as the key step in the synthesis of quinine and quinidine is described. The epoxidation reactions proceed under reagent control with high selectivity and good yield. The effect of sulfide and ylide substituents on the stereochemical outcome of the reaction is discussed. (C) 2010 Elsevier Ltd. All rights reserved.