(4S,5R)-5-(1,3-benzodioxol-5-yl)-3,4-dimethyl-1,3-oxazolidin-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (4S,5R)-5-(1,3-benzodioxol-5-yl)-3,4-dimethyl-1,3-oxazolidin-2-one
• 化学式: C₁₂H₁₃NO₄
• 分子量: 235.24
• InChiKey: JEKJUZJQSGWHKN-CPCISQLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S,5R)-5-(1,3-benzodioxol-5-yl)-3,4-dimethyl-1,3-oxazolidin-2-one 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 (S)-亚甲二氧基甲基苯丙胺; (S)-(+)-3,4-(亚甲二氧基)甲基苯丙胺
  参考文献：
  名称：

  Stereoselective Synthesis of (S)-3,4-Methylenedioxyamphetamines from (R)-Cyanohydrins

  摘要：

  AbstractA stereoselective synthesis of (S)‐3,4‐methylenedioxyamphetamines (S)‐7, which are highly interesting as psychoactive compounds, is described. Starting from readily available (R)‐cyanohydrins (R)‐2 the 2‐amino‐1‐aryl alcohols (1R,2S)‐4 were obtained with high diastereoselectivity by addition of Grignard reagents to the O‐protected cyanohydrins (R)‐3, transimination of the addition products A with primary amines, and hydrogenation of the imino intermediates B with NaBH4. For the hydrogenation of the benzylic hydroxyl group in the 1,2‐amino alcohols (1R,2S)‐4 a new, very efficient method was developed. The optically pure amphetamines (S)‐7 were obtained under very mild conditions by catalytic hydrogenation of the oxazolidinones (4S,5R)‐6, which were readily available by phosgenation of the amino alcohols (1R,2S)‐4.

  DOI：

  10.1002/chem.19970030825
• 作为产物：
  描述：

  光气 、 在 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.5h， 以91%的产率得到(4S,5R)-5-(1,3-benzodioxol-5-yl)-3,4-dimethyl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Stereoselective Synthesis of (S)-3,4-Methylenedioxyamphetamines from (R)-Cyanohydrins

  摘要：

  AbstractA stereoselective synthesis of (S)‐3,4‐methylenedioxyamphetamines (S)‐7, which are highly interesting as psychoactive compounds, is described. Starting from readily available (R)‐cyanohydrins (R)‐2 the 2‐amino‐1‐aryl alcohols (1R,2S)‐4 were obtained with high diastereoselectivity by addition of Grignard reagents to the O‐protected cyanohydrins (R)‐3, transimination of the addition products A with primary amines, and hydrogenation of the imino intermediates B with NaBH4. For the hydrogenation of the benzylic hydroxyl group in the 1,2‐amino alcohols (1R,2S)‐4 a new, very efficient method was developed. The optically pure amphetamines (S)‐7 were obtained under very mild conditions by catalytic hydrogenation of the oxazolidinones (4S,5R)‐6, which were readily available by phosgenation of the amino alcohols (1R,2S)‐4.

  DOI：

  10.1002/chem.19970030825

文献信息

• METHODS FOR TREATING OR PREVENTING CARDIOVASCULAR DISORDERS AND LOWERING RISK OF CARDIOVASCULAR EVENTS
  申请人：DALCOR PHARMA UK LTD., STOCKPORT ZUG BRANCH

  公开号：US20190070178A1

  公开（公告）日：2019-03-07

  The invention provides compositions and methods useful for treating or preventing cardiovascular disorders and lowering risk of cardiovascular events.
• METHODS FOR DELAYING OCCURRENCE OF NEW-ONSET TYPE 2 DIABETES AND FOR SLOWING PROGRESSION OF AND TREATING TYPE 2 DIABETES
  申请人：Dalcor Pharma UK Ltd., Leatherhead, Zug Branch

  公开号：US20210236442A1

  公开（公告）日：2021-08-05

  The invention provides compositions and methods useful for delaying occurrence of new-onset type 2 diabetes, slowing progression of type 2 diabetes, treating type 2 diabetes, and slowing progression of a complication of type 2 diabetes.
• US8735435B2
  申请人：——

  公开号：US8735435B2

  公开（公告）日：2014-05-27