(1R,2S)-2-(p-toluenesulfonamido)-1-phenylpropyl methanesulfonate | 1196985-97-3

• 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: (1R,2S)-2-(p-toluenesulfonamido)-1-phenylpropyl methanesulfonate
• 英文别名: [(1R,2S)-2-[(4-methylphenyl)sulfonylamino]-1-phenylpropyl] methanesulfonate
• CAS: 1196985-97-3
• 化学式: C₁₇H₂₁NO₅S₂
• 分子量: 383.489
• InChiKey: TWWZPKIZWIHARU-YOEHRIQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R,2S)-2-(p-toluenesulfonamido)-1-phenylpropyl methanesulfonate 在 肼 作用下， 以 四氢呋喃 为溶剂， 生成 (2S,3S)-2-methyl-3-phenyl-1-tosylaziridine
  参考文献：
  名称：

  A facile, one-pot synthesis of Ephedra-based aziridines

  摘要：

  A series of enantiomerically and diastereomerically enriched N-sulfonylaziridines have been prepared by a single-pot process from (1R,2S)- and (1S,2R)-norephedrine and (1S,2S)-pseudonorephedrine. The cyclization process involved N-sulfonylation of the Ephedra alkaloid followed by O-sulfonylation with methanesulfonyl chloride. The bis(sulfonyl) Ephedra derivatives were treated with either hydrazine or sodium hydroxide to afford the N-sulfonylaziridines. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.07.016
• 作为产物：
  描述：

  (1R,2S)-[N-(4-甲基苯基)磺酰基]去甲麻黄碱 、 甲基磺酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (1R,2S)-2-(p-toluenesulfonamido)-1-phenylpropyl methanesulfonate
  参考文献：
  名称：

  A facile, one-pot synthesis of Ephedra-based aziridines

  摘要：

  A series of enantiomerically and diastereomerically enriched N-sulfonylaziridines have been prepared by a single-pot process from (1R,2S)- and (1S,2R)-norephedrine and (1S,2S)-pseudonorephedrine. The cyclization process involved N-sulfonylation of the Ephedra alkaloid followed by O-sulfonylation with methanesulfonyl chloride. The bis(sulfonyl) Ephedra derivatives were treated with either hydrazine or sodium hydroxide to afford the N-sulfonylaziridines. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.07.016

文献信息

• A facile, one-pot synthesis of Ephedra-based aziridines
  作者：Jonathan A. Groeper、Joel B. Eagles、Shawn R. Hitchcock

  DOI：10.1016/j.tetasy.2009.07.016

  日期：2009.9

  A series of enantiomerically and diastereomerically enriched N-sulfonylaziridines have been prepared by a single-pot process from (1R,2S)- and (1S,2R)-norephedrine and (1S,2S)-pseudonorephedrine. The cyclization process involved N-sulfonylation of the Ephedra alkaloid followed by O-sulfonylation with methanesulfonyl chloride. The bis(sulfonyl) Ephedra derivatives were treated with either hydrazine or sodium hydroxide to afford the N-sulfonylaziridines. (C) 2009 Elsevier Ltd. All rights reserved.