1-Benzoyl-2-methoxy-5-(methoxycarbonyl)pyrrolidine | 195727-70-9

• 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: 1-Benzoyl-2-methoxy-5-(methoxycarbonyl)pyrrolidine
• 英文别名: methyl (2S)-1-benzoyl-5-methoxypyrrolidine-2-carboxylate
• CAS: 195727-70-9
• 化学式: C₁₄H₁₇NO₄
• 分子量: 263.293
• InChiKey: JUCKEOFLGZWKHZ-PXYINDEMSA-N

物化性质

• 沸点：
  386.2±42.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 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：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-Benzoyl-2-methoxy-5-(methoxycarbonyl)pyrrolidine 在 lithium aluminium tetrahydride 、 copper(I) bromide dimethylsulfide complex 、 三氟化硼乙醚 作用下， 以 四氢呋喃 为溶剂， 生成 [(2S,5S)-1-benzyl-5-propylpyrrolidin-2-yl]methanol
  参考文献：
  名称：

  Synthesis of (-)-Pseudoconhydrine through Ring Enlargement of a L-Proline Derivative

  摘要：

  通过环扩大反应，以L-脯氨酸为原料，简述了（-）-伪粗榧碱的短合成方法。

  DOI：

  10.1055/s-1997-5789
• 作为产物：
  描述：

  N-苯甲酰基-l-脯氨酸 在 potassium carbonate 、 四乙基对甲苯磺酸铵 作用下， 生成 1-Benzoyl-2-methoxy-5-(methoxycarbonyl)pyrrolidine
  参考文献：
  名称：

  Synthesis of (-)-Pseudoconhydrine through Ring Enlargement of a L-Proline Derivative

  摘要：

  通过环扩大反应，以L-脯氨酸为原料，简述了（-）-伪粗榧碱的短合成方法。

  DOI：

  10.1055/s-1997-5789

文献信息

• Diastereoselective arylation of l-proline derivatives at the 5-position
  作者：Osamu Onomura、Peter G. Kirira、Toshimitsu Tanaka、Shinsuke Tsukada、Yoshihiro Matsumura、Yosuke Demizu

  DOI：10.1016/j.tet.2008.06.004

  日期：2008.8

  Diastereoselective introduction of nucleophiles into L-proline derivatives at the 5-position was achieved with suitable selection of N-protecting group. N-Methoxycarbonylated or benzyloxycarbonylated L-proline derivatives reacted with arene to give cis-arylated products. On the other hand, N-benzoylated L-proline derivative preferentially gave trans-arylated product, which could be easily transformed into optically active C-2-symmetrical pyrrolidine derivative. Such derivative 5 worked well as an organic activator in the asymmetric reduction of aromatic imines by Cl3SiH. (C) 2008 Elsevier Ltd. All rights reserved.
• Electroorganic chemistry. 81. Anodic oxidation of sulfonamides and amidophosphates
  作者：Tatsuya Shono、Yoshihiro Matsumura、Kenji Tsubata、Kenshi Uchida、Takenobu Kanazawa、Kunio Tsuda

  DOI：10.1021/jo00194a008

  日期：1984.10
• Facile synthesis of both enantiomers of (pyrrolidin-2-yl)phosphonate from l-proline
  作者：Shigeo Hirata、Masami Kuriyama、Osamu Onomura

  DOI：10.1016/j.tet.2011.09.080

  日期：2011.12

  Diastereoselective introduction of phosphono groups into L-proline derivatives at the 5-position was achieved with suitable selection of N-protecting group. N-Benzoyl-L-prolinate preferentially gave trans-phosphorylated products, which could be easily transformed into (S)-(pyrrolidin-2-yl)phosphonates. On the other hand, N-benzyloxycarbonyl-L-prolinate reacted with phosphite to give cis-substituted products, which could be easily transformed into (R)-(pyrrolidin-2-yl)phosphonates. (C) 2011 Elsevier Ltd. All rights reserved.