methyl N-benzyloxycarbonyl-5-(2,4,6-trimethylphenyl)-L-prolinate | 1123177-52-5

• 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: methyl N-benzyloxycarbonyl-5-(2,4,6-trimethylphenyl)-L-prolinate
• 英文别名: 1-O-benzyl 2-O-methyl (2S,5R)-5-(2,4,6-trimethylphenyl)pyrrolidine-1,2-dicarboxylate
• CAS: 1123177-52-5
• 化学式: C₂₃H₂₇NO₄
• 分子量: 381.472
• InChiKey: QMCSTBKTEMVIIY-UXHICEINSA-N

物化性质

• 沸点：
  515.7±50.0 °C(Predicted)
• 密度：
  1.160±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-benzyl 2-methyl (2S)-5-methoxypyrrolidine-1,2-dicarboxylate 、 均三甲苯 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 以68%的产率得到methyl N-benzyloxycarbonyl-5-(2,4,6-trimethylphenyl)-L-prolinate
  参考文献：
  名称：

  Diastereoselective arylation of l-proline derivatives at the 5-position

  摘要：

  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.

  DOI：

  10.1016/j.tet.2008.06.004

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.