(4S,5R)-5-(1,3-benzodioxol-5-yl)-3-ethyl-4-methyl-1,3-oxazolidin-2-one | 197787-10-3

• 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-ethyl-4-methyl-1,3-oxazolidin-2-one
• CAS: 197787-10-3
• 化学式: C₁₃H₁₅NO₄
• 分子量: 249.266
• InChiKey: YYEQKVMIBRHWCY-UFBFGSQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 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-ethyl-4-methyl-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 5.0h， 生成 MDEA
  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：

  (R)-2-hydroxy-2-(3,4-methylenedioxyphenyl)acetonitrile 在 吡啶 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 5.5h， 生成 (4S,5R)-5-(1,3-benzodioxol-5-yl)-3-ethyl-4-methyl-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

• Cetp Inhibitors
  申请人：Ali Amjad

  公开号：US20080119476A1

  公开（公告）日：2008-05-22

  Compounds having the structures of Formula I, including pharmaceutically acceptable salts of the compounds, are CETP inhibitors, and are useful for raising HDL-cholesterol, reducing LDL-cholesterol, and for treating or preventing atherosclerosis: In the compounds of Formula I, B or R 2 is a phenyl group which has an ortho aryl, heterocyclic, benzoheterocyclic or benzocycloalkyl substituent, and one other position on the 5-membered ring has an aromatic, heterocyclic, cycloalkyl, benzoheterocyclic or benzocycloalkyl substituent connected directly to the ring or attached to the ring through a —CH 2 —.

  具有公式I结构的化合物，包括化合物的药物可接受的盐，是CETP抑制剂，可用于提高HDL-胆固醇，降低LDL-胆固醇，以及治疗或预防动脉粥样硬化。在公式I的化合物中，B或R2是具有正交芳基，杂环，苯并杂环或苯并环烷基取代基的苯基基团，5元环上的另一个位置具有芳基，杂环，环烷基，苯并杂环或苯并环烷基取代基，直接连接到环或通过-CH2-附加到环上。
• CETP INHIBITORS
  申请人：ALI Amjad

  公开号：US20100099716A1

  公开（公告）日：2010-04-22

  Compounds having the structures of Formula I, including pharmaceutically acceptable salts of the compounds, are CETP inhibitors, and are useful for raising HDL-cholesterol, reducing LDL-cholesterol, and for treating or preventing atherosclerosis: In the compounds of Formula I, B or R 2 is a phenyl group which has an ortho aryl, heterocyclic, benzoheterocyclic or benzocycloalkyl substituent, and one other position on the 5-membered ring has an aromatic, heterocyclic, cycloalkyl, benzoheterocyclic or benzocycloalkyl substituent connected directly to the ring or attached to the ring through a —CH 2 —.

  具有I式结构的化合物，包括该化合物的药物可接受的盐，是CETP抑制剂，可用于提高HDL胆固醇，降低LDL胆固醇，并用于治疗或预防动脉粥样硬化。在I式化合物中，B或R2是具有正交芳香族，杂环，苯并杂环或苯并环烷基取代基的苯基，而5元环上的另一个位置具有直接连接到环或通过-CH2-连接到环的芳香族，杂环，环烷基，苯并杂环或苯并环烷基取代基。
• US7652049B2
  申请人：——

  公开号：US7652049B2

  公开（公告）日：2010-01-26
• Stereoselective Synthesis of (S)-3,4-Methylenedioxyamphetamines from (R)-Cyanohydrins
  作者：Franz Effenberger、Jürgen Jäger

  DOI：10.1002/chem.19970030825

  日期：1997.8

  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.