(+/-)-(4R^*,5R^*)-5-(ethoxycarbonyl)-1-methyl-4-phenylpyrrolidin-2-one | 109838-79-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (+/-)-(4R^*,5R^*)-5-(ethoxycarbonyl)-1-methyl-4-phenylpyrrolidin-2-one
• 英文别名: (+/-)-(4RS,5RR)-5-(ethoxycarbonyl)-1-methyl-4-phenylpyrrolidin-2-one；(+/-)-(4RS,5RS)-5-ethyl-1-methyl-4-phenylpyrrolidin-2-one；(+/-)-(4R*,5R*)-5-(ethoxycarbonyl)-1-methyl-4-phenylpyrrolidin-2-one；ethyl (2R,3R)-1-methyl-5-oxo-3-phenylpyrrolidine-2-carboxylate
• CAS: 109838-79-1；109838-80-4
• 化学式: C₁₄H₁₇NO₃
• 分子量: 247.294
• InChiKey: AORIFMYCIDPVHG-DGCLKSJQSA-N

物化性质

• 沸点：
  391.9±42.0 °C(Predicted)
• 密度：
  1.152±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  (+/-)-(4R^*,5R^*)-5-(ethoxycarbonyl)-1-methyl-4-phenylpyrrolidin-2-one 在 lithium aluminium tetrahydride 作用下， 以72.4%的产率得到(+/-)-(4R^*,5R^*)-5-(hydroxymethyl)-1-methyl-4-phenylpyrrolidin-2-one
  参考文献：
  名称：

  （ - ） -黄皮和（+）替代性合成-的4-和6- desphenyl类似物外延-clausenamide

  摘要：

  分别由市售的d-焦谷氨酸和已知的外消旋吡咯烷酮13以旋光活性形式制备（-）-clausenamide的4-和6-去苯基类似物6和7。为了证实的（+）的绝对立体化学-和（ - ） - 7，中间19B被转移到（+） -外延-clausenamide 8。

  DOI：

  10.1016/j.cclet.2011.07.002
• 作为产物：
  描述：

  5,5-Diethoxycarbonyl-1-methyl-4-phenyl-pyrrolidin-2-one 在 barium dihydroxide 作用下， 以 乙醇 为溶剂， 反应 0.33h， 生成 (+/-)-(4R^*,5R^*)-5-(ethoxycarbonyl)-1-methyl-4-phenylpyrrolidin-2-one
  参考文献：
  名称：

  Diastereoselective and enantioselective total synthesis of the hepatoprotective agent clausenamide

  摘要：

  DOI：

  10.1021/jo00228a037

文献信息

• 4,5-Disubstituted cis-pyrrolidinones as inhibitors of type II 17β-hydroxysteroid dehydrogenase. Part 3. Identification of lead candidate
  作者：Jill Wood、Cedo M. Bagi、Christiana Akuche、Antonietta Bacchiocchi、Jeremy Baryza、Marie-Luise Blue、Catherine Brennan、Ann-Marie Campbell、Soongyu Choi、James H. Cook、Patricia Conrad、Brian R. Dixon、Paul P. Ehrlich、Todd Gane、David Gunn、Ted Joe、Jeffrey S. Johnson、Jerold Jordan、Richard Kramss、Peiying Liu、Joan Levy、Derek B. Lowe、Ian McAlexander、Reina Natero、Anikó M. Redman、William J. Scott、Christopher Town、Ming Wang、Yamin Wang、Zhonghua Zhang

  DOI：10.1016/j.bmcl.2006.06.041

  日期：2006.9

  A series of 4,5-disubstituted cis-pyrrolidinones was investigated as inhibitors of 17beta-HSD II for the treatment of osteoporosis. Biochemical data for several compounds are given. Compound 42 was selected as the lead candidate.

  研究了一系列4,5-二取代的顺式-吡咯烷酮作为17β-HSDII抑制剂，用于治疗骨质疏松症。给出了几种化合物的生化数据。选择化合物42作为主要候选化合物。
• 17-Beta-hydroxysteroid dehydrogenase-II inhibitors
  申请人：——

  公开号：US20030087952A1

  公开（公告）日：2003-05-08

  17-beta-hydroxysteroid dehydrogenase-I1 inhibitors having the structural formula 1 wherein the phenyl group labeled A and the group —C(R 4 )(R 6 )Y are oriented cis to each other; W represents 0 or S; R 1 represents —H or optionally substituted —(C 1 -C 4 )alkyl; n represents 0 or an integer of 1-3; and R 2 represents any of a variety of substituents on ring A. R 4 generally represents —H but may be a bond terminating at the ortho position of ring A. Y represents fluorine, —OR 5 , or —SR 5 , and R 5 represents —H. optionally substituted —(C 1 -C 4 )alkyl, optionally substituted -phenyl, optionally substituted —(C 1 -C 4 )alkyl-phenyl, or optionally substituted —(C 1 -C 4 )acyl. R 6 represents any of a variety of groups as defined in the specification and claims, including heteroaryl, arylalkyl, heteroarylalkyl, arylalkenyl, heteroarylalkenyl, alkynyl, arylalkynyl, heteroarylalkynyl, aryl, and indolyl. Pharmaceutically acceptable salts and N-oxides of these materials are also included. Also claimed are pharmaceutical compositions containing these materials and methods of using them.

  17-beta-羟基类固醇脱氢酶I1抑制剂具有结构式1，其中苯基A和基团—C(R4)(R6)Y相对取向；W代表0或S；R1代表—H或可选择取代的—(C1-C4)烷基；n代表0或1-3的整数；R2代表环A上的各种取代基之一。R4通常代表—H，但可能是终止在环A的邻位的键。Y代表氟、—OR5或—SR5，R5代表—H、可选择取代的—(C1-C4)烷基、可选择取代的苯基、可选择取代的—(C1-C4)烷基-苯基或可选择取代的—(C1-C4)酰基。R6代表根据说明书和索赔中定义的各种基团之一，包括杂芳基、芳基烷基、杂芳基烷基、芳基烯基、杂芳基烯基、炔基、芳基炔基、杂芳基炔基、芳基和吲哚基。还包括这些物质的药用合适盐和N-氧化物。还声明包含这些物质的药物组合物和使用它们的方法。
• 17-beta-hydroxysteroid dehydrogenase-II inhibitors
  申请人：Bayer Pharmaceuticals Corporation

  公开号：US06784167B2

  公开（公告）日：2004-08-31

  17-beta-hydroxysteroid dehydrogenase-II inhibitors having the structural formula wherein the phenyl group labeled A and the group —C(R4)(R6)Y are oriented cis to each other; W represents O or S; R1 represents —H or optionally substituted —(C1-C4)alkyl; n represents 0 or an integer of 1-3; and R2 represents any of a variety of substituents on ring A. R4 generally represents —H but may be a bond terminating at the ortho position of ring A. Y represents fluorine, —OR5, or —SR5, and R5 represents —H, optionally substituted —(C1-C4)alkyl, optionally substituted -phenyl, optionally substituted —(C1-C4)alkyl-phenyl, or optionally substituted —(C1-C4)acyl. R6 represents any of a variety of groups as defined in the specification and claims, including heteroaryl, arylalkyl, heteroarylalkyl, arylalkenyl, heteroarylalkenyl, alkynyl, arylalkynyl, heteroarylalkynyl, aryl, and indolyl. Pharmaceutically acceptable salts and N-oxides of these materials are also included. Also claimed are pharmaceutical compositions containing these materials and methods of using them.

  具有以下结构式的17-beta-羟基类固醇脱氢酶-II抑制剂，其中标记为A的苯基和群体—C（R4）（R6）Y定向为顺式构型；W代表O或S；R1代表—H或可选取代的—（C1-C4）烷基；n代表0或1-3的整数；R2代表环A上的各种取代基。R4通常代表—H，但可能是终止于环A的邻位的键。Y代表氟，—OR5或—SR5，R5代表—H，可选取代的—（C1-C4）烷基，可选取代的苯基，可选取代的—（C1-C4）烷基-苯基或可选取代的—（C1-C4）酰基。R6代表规范和权利要求中定义的各种群体，包括杂环芳基，芳基烷基，杂环芳基烷基，芳基烯基，杂环芳基烯基，炔基，芳基炔基，杂环芳基炔基，芳基和吲哚基。还包括这些材料的药学上可接受的盐和N-氧化物。还声明了含有这些材料的制药组合物和使用它们的方法。
• 4,5-Disubstituted cis-pyrrolidinones as inhibitors of 17β-hydroxysteroid dehydrogenase II. Part 1: Synthetic approach
  作者：James H. Cook、Jeremy Barzya、Catherine Brennan、Derek Lowe、Yamin Wang、Anikó Redman、William J. Scott、Jill E. Wood

  DOI：10.1016/j.tetlet.2005.01.003

  日期：2005.2

  17beta-Hydroxysteroid dehydrogenase II (17beta-HSD II) antagonists may provide an important way into preventing the onset of osteoporosis. The discovery of 4,5-disubstituted eis-pyrrolidinones as 17beta-HSD II inhibitors led to the development of an efficient intramolecular Michael addition, followed by catalytic hydrogenation to obtain the desired cis configuration. (C) 2005 Elsevier Ltd. All rights reserved.
• HARTWIG, WOLFGANG;BENZ, ULRICH
  作者：HARTWIG, WOLFGANG、BENZ, ULRICH

  DOI：——

  日期：——