tert-butyl (2S)-N-(3-hydroxy-2-methylpropyl)-N-(toluene-4-sulfonyl)carbamate | 1192544-74-3

• 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: tert-butyl (2S)-N-(3-hydroxy-2-methylpropyl)-N-(toluene-4-sulfonyl)carbamate
• 英文别名: tert-butyl N-[(2S)-3-hydroxy-2-methylpropyl]-N-(4-methylphenyl)sulfonylcarbamate
• CAS: 1192544-74-3
• 化学式: C₁₆H₂₅NO₅S
• 分子量: 343.444
• InChiKey: AVBZNPZPXJRAQA-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  92.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S)-N-(3-hydroxy-2-methylpropyl)-N-(toluene-4-sulfonyl)carbamate 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以90%的产率得到tert-butyl (2S)-N-(2-methyl-3-oxopropyl)-N-(toluene-4-sulfonyl)carbamate
  参考文献：
  名称：

  Stereocontrolled preparation of bicyclic alkaloid analogues: an approach towards the kinabalurine skeleton

  摘要：

  An approach towards the construction of bicyclic analogues of monoterpene alkaloids belonging to the kinabalurine, incarvilline and skytanthine families Of natural products is reported These syntheses rely oil a stereoselective intramolecular Pauson-Khand cyclisation of a chiral pool-derived enyne in order to prepare the bicyclic core Stereoselective further elaboration generates diastereomeric analogues of the naturally occurring alkaloids (C) 2009 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tet.2009.07.060
• 作为产物：
  描述：

  methyl (2S)-3-[N-(tert-butoxycarbonyl)-N-(4-methylphenylsulfonyl)]amino-2-methylpropanoate 在 lithium aluminium tetrahydride 、 水 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以100%的产率得到tert-butyl (2S)-N-(3-hydroxy-2-methylpropyl)-N-(toluene-4-sulfonyl)carbamate
  参考文献：
  名称：

  Stereocontrolled preparation of bicyclic alkaloid analogues: an approach towards the kinabalurine skeleton

  摘要：

  An approach towards the construction of bicyclic analogues of monoterpene alkaloids belonging to the kinabalurine, incarvilline and skytanthine families Of natural products is reported These syntheses rely oil a stereoselective intramolecular Pauson-Khand cyclisation of a chiral pool-derived enyne in order to prepare the bicyclic core Stereoselective further elaboration generates diastereomeric analogues of the naturally occurring alkaloids (C) 2009 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tet.2009.07.060

文献信息

• Stereocontrolled preparation of bicyclic alkaloid analogues: an approach towards the kinabalurine skeleton
  作者：Yvonne Kavanagh、Matthew O'Brien、Paul Evans

  DOI：10.1016/j.tet.2009.07.060

  日期：2009.9

  An approach towards the construction of bicyclic analogues of monoterpene alkaloids belonging to the kinabalurine, incarvilline and skytanthine families Of natural products is reported These syntheses rely oil a stereoselective intramolecular Pauson-Khand cyclisation of a chiral pool-derived enyne in order to prepare the bicyclic core Stereoselective further elaboration generates diastereomeric analogues of the naturally occurring alkaloids (C) 2009 Elsevier Ltd All rights reserved