(2S,5R)-1-benzyl 2-methyl 5-(5-oxocyclopent-1-en-1-yl)pyrrolidine-1,2-dicarboxylate | 1244025-22-6

• 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,5R)-1-benzyl 2-methyl 5-(5-oxocyclopent-1-en-1-yl)pyrrolidine-1,2-dicarboxylate
• CAS: 1244025-22-6
• 化学式: C₁₉H₂₁NO₅
• 分子量: 343.379
• InChiKey: BTNBYSZDKANGEE-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  72.91
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 (2S,5R)-1-benzyl 2-methyl 5-(5-oxocyclopent-1-en-1-yl)pyrrolidine-1,2-dicarboxylate 、 (2S,5S)-1-benzyl 2-methyl 5-(5-oxocyclopent-1-en-1-yl)pyrrolidine-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