tert-butyl 4-iodo-2,3-dihydro-1H-pyrrole-1-carboxylate | 1196146-93-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: tert-butyl 4-iodo-2,3-dihydro-1H-pyrrole-1-carboxylate
• 英文别名: tert-butyl 4-iodo-2,3-dihydropyrrole-1-carboxylate
• CAS: 1196146-93-6
• 化学式: C₉H₁₄INO₂
• 分子量: 295.12
• InChiKey: DMJOQIZANGFYFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-iodo-2,3-dihydro-1H-pyrrole-1-carboxylate 在 barium hydroxide octahydrate 、 palladium diacetate 、 三乙酰氧基硼氢化钠 、 溶剂黄146 、 2-(二环己基膦基)联苯 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 7.0h， 生成 tert-butyl 4-(2-(benzylamino)phenyl)-2,3-dihydro-1H-pyrrole-1-carboxylate
  参考文献：
  名称：

  A Short Total Synthesis of (±)-Epimeloscine and (±)-Meloscine Enabled by a Cascade Radical Annulation of a Divinylcyclopropane

  摘要：

  The first stereoselective synthesis of epimeloscine has been accomplished in 13 total steps with a longest linear sequence of 10 steps. The core of the synthesis takes only five steps, the key ones being acylation, stereoselective tandem radical cyclization of a divinylcyclopropane to make two rings, and group-selective ring-closing metathesis of the resulting divinylcyclopentane to make the last ring.

  DOI：

  10.1021/ja2042854
• 作为产物：
  描述：

  trans-tert-butyl 3-iodo-2-methoxypyrrolidine-1-carboxylate 在 柠檬酸 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以42%的产率得到tert-butyl 4-iodo-2,3-dihydro-1H-pyrrole-1-carboxylate
  参考文献：
  名称：

  A Short Total Synthesis of (±)-Epimeloscine and (±)-Meloscine Enabled by a Cascade Radical Annulation of a Divinylcyclopropane

  摘要：

  The first stereoselective synthesis of epimeloscine has been accomplished in 13 total steps with a longest linear sequence of 10 steps. The core of the synthesis takes only five steps, the key ones being acylation, stereoselective tandem radical cyclization of a divinylcyclopropane to make two rings, and group-selective ring-closing metathesis of the resulting divinylcyclopentane to make the last ring.

  DOI：

  10.1021/ja2042854

文献信息

• Radical [3 + 2]-Annulation of Divinylcyclopropanes: Rapid Synthesis of Complex Meloscine Analogs
  作者：Hanmo Zhang、Kyu Ok Jeon、E. Ben Hay、Steven J. Geib、Dennis P. Curran、Matthew G. LaPorte

  DOI：10.1021/ol403078e

  日期：2014.1.3

  A radical [3 + 2]-divinylcyclopropane annulation cascade has been extended to encompass five D-ring variants of the meloscine/epimeloscine core structure. Representative ABCD tetracyclic intermediates were further elaborated with novel substituted E-rings through subsequent transformations of advanced intermediates that provided opportunities for late-stage variation of the B-ring (lactam) N-substituents which were also developed.