(2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octane-4,8-dione | 511543-55-8

• 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: (2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octane-4,8-dione
• 英文别名: (2R,5S)-2-Trichloromethyl-3-oxa-1-azabicyclo[3,3,0]octane-4,8-dione；(3R,7aS)-3-(trichloromethyl)-3,6,7,7a-tetrahydropyrrolo[1,2-c][1,3]oxazole-1,5-dione
• CAS: 511543-55-8
• 化学式: C₇H₆Cl₃NO₃
• 分子量: 258.489
• InChiKey: ZKEXSVJKCZVQIH-BBIVZNJYSA-N

物化性质

• 沸点：
  437.4±45.0 °C(Predicted)
• 密度：
  1.71±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  (2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octane-4,8-dione 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.0h， 生成 (S)-1-phenylethyl((S)-pyrrolidin-2-ylmethyl)amine
  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：

  三氯乙醛 、 L-焦谷氨酸 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以91%的产率得到(2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octane-4,8-dione
  参考文献：
  名称：

  Synthesis of chiral diamines using novel 2-trichloromethyloxazolidin-4-one precursors derived from 5-oxo-proline and proline

  摘要：

  Efficient syntheses of chiral vicinal diamines derived from (S)-oxo-proline and (S)-proline are described. The novel diastereomerically pure precursor (2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo-[3.3.0]-octan-4,8-dione 3 and its enantiomer are readily available by reaction of the inexpensive enantiomers of 5-oxo-proline with chloral. Compound 3 reacts with primary and secondary amines to afford the 5-oxo-prolylamides 4 in quantitative yield. In contrast, the (S)-proline-derived precursor (2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one 6 gave (S)-N-formylprolylamides 9 and/or (S)-prolylamides 8 depending on the reaction conditions. Upon reduction with LiAlH4, amides 4 and 9 afforded the proline-derived (S)-2-(alkylaminomethyl)pyrrolidines 1 and (S)-N- methyl-2-(alkylaminomethyl)-pyrrolidines 5 in 70-90% yields. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00579-7

文献信息

• Synthesis of chiral diamines using novel 2-trichloromethyloxazolidin-4-one precursors derived from 5-oxo-proline and proline
  作者：Mohamed Amedjkouh、Per Ahlberg

  DOI：10.1016/s0957-4166(02)00579-7

  日期：2002.10

  Efficient syntheses of chiral vicinal diamines derived from (S)-oxo-proline and (S)-proline are described. The novel diastereomerically pure precursor (2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo-[3.3.0]-octan-4,8-dione 3 and its enantiomer are readily available by reaction of the inexpensive enantiomers of 5-oxo-proline with chloral. Compound 3 reacts with primary and secondary amines to afford the 5-oxo-prolylamides 4 in quantitative yield. In contrast, the (S)-proline-derived precursor (2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one 6 gave (S)-N-formylprolylamides 9 and/or (S)-prolylamides 8 depending on the reaction conditions. Upon reduction with LiAlH4, amides 4 and 9 afforded the proline-derived (S)-2-(alkylaminomethyl)pyrrolidines 1 and (S)-N- methyl-2-(alkylaminomethyl)-pyrrolidines 5 in 70-90% yields. (C) 2002 Elsevier Science 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.