(2S)-5-oxo-2-(4-chloroanilinocarbonyl)pyrrolidine | 944453-17-2

• 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: (2S)-5-oxo-2-(4-chloroanilinocarbonyl)pyrrolidine
• 英文别名: (S)-N-(4-chlorophenyl)-5-oxopyrrolidine-2-carboxamide；(2S)-N-(4-chlorophenyl)-5-oxopyrrolidine-2-carboxamide
• CAS: 944453-17-2
• 化学式: C₁₁H₁₁ClN₂O₂
• mdl: MFCD00852273
• 分子量: 238.674
• InChiKey: VMKVDCUAGWPHJJ-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S)-5-oxo-2-(4-chloroanilinocarbonyl)pyrrolidine 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以70.7%的产率得到(S)-4-chloro-N-(pyrrolidin-2-ylmethyl)aniline
  参考文献：
  名称：

  Synthesis and characterization of chiral 1,2-diamines from 5-oxo-pyrrolidine-(S)-2-carboxylic acid

  摘要：

  Unsymmetrical chiral secondary vicinal diamines were synthesized by applying a modified three-step reaction. The key step in this sequence is a primary amine mediated ring opening reaction of a diastereomeric oxazolidinone derivative. A possible mechanism for this step is described. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.07.012
• 作为产物：
  描述：

  L-焦谷氨酸 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 (2S)-5-oxo-2-(4-chloroanilinocarbonyl)pyrrolidine
  参考文献：
  名称：

  Chiral diamides as efficient catalytic precursors for the borane-mediated asymmetric reduction of prochiral ketones

  摘要：

  Chiral diamides [(2S)-5-oxo-2-(arylamino)carbonylpyrrolidines] derived from the abundantly available (S)-glutamic/(S)-pyroglutamic acids were successfully utilized as effective chiral catalytic precursors in the borane-mediated asymmetric reduction of prochiral ketones in refluxing toluene, to provide the corresponding secondary alcohols with up to 91% enantiomeric purities. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.03.034

文献信息

• Investigation of 2-oxopyrrolidine 5-carboxylic acid amides derivatives as potential anti-tubercular agents based on the similarity screening results from molecular fingerprints and swiss similarity
  作者：Nagasree, K. P.、Umarani, W. A.、Sony, K. P. K.、Kumar, K. S.、Murali Krishna Kumar, M.

  DOI：10.56042/ijc.v62i1.70391

  日期：——
• Chiral diamides as efficient catalytic precursors for the borane-mediated asymmetric reduction of prochiral ketones
  作者：Deevi Basavaiah、Kalapala Venkateswara Rao、Bhavanam Sekhara Reddy

  DOI：10.1016/j.tetasy.2007.03.034

  日期：2007.5

  Chiral diamides [(2S)-5-oxo-2-(arylamino)carbonylpyrrolidines] derived from the abundantly available (S)-glutamic/(S)-pyroglutamic acids were successfully utilized as effective chiral catalytic precursors in the borane-mediated asymmetric reduction of prochiral ketones in refluxing toluene, to provide the corresponding secondary alcohols with up to 91% enantiomeric purities. (c) 2007 Elsevier Ltd. All rights reserved.
• Synthesis and characterization of chiral 1,2-diamines from 5-oxo-pyrrolidine-(S)-2-carboxylic acid
  作者：Uwe Köhn、Andrea Schramm、Florian Kloß、Helmar Görls、Evelyn Arnold、Ernst Anders

  DOI：10.1016/j.tetasy.2007.07.012

  日期：2007.7

  Unsymmetrical chiral secondary vicinal diamines were synthesized by applying a modified three-step reaction. The key step in this sequence is a primary amine mediated ring opening reaction of a diastereomeric oxazolidinone derivative. A possible mechanism for this step is described. (c) 2007 Elsevier Ltd. All rights reserved.