(2S)-dibenzyl 5-methoxypyrrolidine-1,2-dicarboxylate | 1244025-18-0

• 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)-dibenzyl 5-methoxypyrrolidine-1,2-dicarboxylate
• 英文别名: dibenzyl (2S)-5-methoxypyrrolidine-1,2-dicarboxylate
• CAS: 1244025-18-0
• 化学式: C₂₁H₂₃NO₅
• 分子量: 369.417
• InChiKey: NRZCKUOMKFRHSR-OYKVQYDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S)-dibenzyl 5-methoxypyrrolidine-1,2-dicarboxylate 、 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of highly functionalized 2,5-disubstituted pyrrolidines via an aza-Morita–Baylis–Hillman-type reaction

  摘要：

  An aza-Morita-Baylis-Hillman-type reaction of Michael acceptors with 5-substituted cyclic N,O-acetals derived from pyrrolidines has been investigated. It has been found that the combination of Me2S and TMSOTf work well with unhindered and reactive enals and enones whilst the use of quinuclidine and TMSOTf is superior for more hindered Michael acceptors. The reactions lead to 2,5-trans-disubstituted pyrrolidines with good to excellent diastereoselectivity. The origin of the selectivity is discussed. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.05.047
• 作为产物：
  描述：

  甲醇 、 (S)-5-Hydroxy-pyrrolidine-1,2-dicarboxylic acid dibenzyl ester 在 对甲苯磺酸 作用下， 反应 2.0h， 以67%的产率得到(2S)-dibenzyl 5-methoxypyrrolidine-1,2-dicarboxylate
  参考文献：
  名称：

  Synthesis of highly functionalized 2,5-disubstituted pyrrolidines via an aza-Morita–Baylis–Hillman-type reaction

  摘要：

  An aza-Morita-Baylis-Hillman-type reaction of Michael acceptors with 5-substituted cyclic N,O-acetals derived from pyrrolidines has been investigated. It has been found that the combination of Me2S and TMSOTf work well with unhindered and reactive enals and enones whilst the use of quinuclidine and TMSOTf is superior for more hindered Michael acceptors. The reactions lead to 2,5-trans-disubstituted pyrrolidines with good to excellent diastereoselectivity. The origin of the selectivity is discussed. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.05.047

文献信息

• Synthesis of highly functionalized 2,5-disubstituted pyrrolidines via an aza-Morita–Baylis–Hillman-type reaction
  作者：James E. Kitulagoda、Anders Palmelund、Varinder K. Aggarwal

  DOI：10.1016/j.tet.2010.05.047

  日期：2010.8

  An aza-Morita-Baylis-Hillman-type reaction of Michael acceptors with 5-substituted cyclic N,O-acetals derived from pyrrolidines has been investigated. It has been found that the combination of Me2S and TMSOTf work well with unhindered and reactive enals and enones whilst the use of quinuclidine and TMSOTf is superior for more hindered Michael acceptors. The reactions lead to 2,5-trans-disubstituted pyrrolidines with good to excellent diastereoselectivity. The origin of the selectivity is discussed. (C) 2010 Elsevier Ltd. All rights reserved.