Methyl 5-oxo-1-(thiophen-2-ylmethyl)pyrrolidine-3-carboxylate | 190784-05-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: Methyl 5-oxo-1-(thiophen-2-ylmethyl)pyrrolidine-3-carboxylate
• CAS: 190784-05-5
• 化学式: C₁₁H₁₃NO₃S
• mdl: MFCD01763892
• 分子量: 239.295
• InChiKey: QITDVVRSFUQQTM-UHFFFAOYSA-N

物化性质

• 沸点：
  403.3±45.0 °C(Predicted)
• 密度：
  1.317±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl 5-oxo-1-(thiophen-2-ylmethyl)pyrrolidine-3-carboxylate 以 三氯氧磷 为溶剂， 反应 6.0h， 生成 5-Chloro-1-thiophen-2-ylmethyl-1H-pyrrole-3-carbaldehyde
  参考文献：
  名称：

  Synthesis of 5-chloropyrrole carboxaldehydes from 5-oxopyrrolidine carboxamides

  摘要：

  N-alkyl-5-chloropyrrole-2(or 3)-carboxaldehydes are obtained by treatment of N-alkyl-5-oxopyrrolidine-2 (or 3)-carboxamides by phosphorus oxychloride and basic hydrolysis. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00597-2
• 作为产物：
  描述：

  2-噻吩甲胺 、 衣康酸二甲酯 生成 Methyl 5-oxo-1-(thiophen-2-ylmethyl)pyrrolidine-3-carboxylate
  参考文献：
  名称：

  Discovery of an orally efficaceous 4-phenoxypyrrolidine-based BACE-1 inhibitor

  摘要：

  Based on a lead compound identified from the patent literature, we developed patentably novel BACE-1 inhibitors by introducing a cyclic amine scaffold as embodied by la and 1b. Extensive SAR studies assessed a variety of isophthalamide replacements including substituted pyrrolidinones and ultimately led to the identification of 11. Due to its favorable overall profile, 11 has been extensively profiled in various in vivo settings. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.053

文献信息

• Discovery of an orally efficaceous 4-phenoxypyrrolidine-based BACE-1 inhibitor
  作者：U. Iserloh、J. Pan、A.W. Stamford、M.E. Kennedy、Q. Zhang、L. Zhang、E.M. Parker、N.A. McHugh、L. Favreau、C. Strickland、J. Voigt

  DOI：10.1016/j.bmcl.2007.10.053

  日期：2008.1

  Based on a lead compound identified from the patent literature, we developed patentably novel BACE-1 inhibitors by introducing a cyclic amine scaffold as embodied by la and 1b. Extensive SAR studies assessed a variety of isophthalamide replacements including substituted pyrrolidinones and ultimately led to the identification of 11. Due to its favorable overall profile, 11 has been extensively profiled in various in vivo settings. (c) 2007 Elsevier Ltd. All rights reserved.
• Synthesis of 5-chloropyrrole carboxaldehydes from 5-oxopyrrolidine carboxamides
  作者：Pierre Netchitaïlo、Mohamed Othman、Adam Daïch、Bernard Decroix

  DOI：10.1016/s0040-4039(97)00597-2

  日期：1997.5

  N-alkyl-5-chloropyrrole-2(or 3)-carboxaldehydes are obtained by treatment of N-alkyl-5-oxopyrrolidine-2 (or 3)-carboxamides by phosphorus oxychloride and basic hydrolysis. (C) 1997 Elsevier Science Ltd.