4-[2-(cyclopent-2-enyl)ethylamino]benzoic acid tert-butyl ester | 861104-09-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-[2-(cyclopent-2-enyl)ethylamino]benzoic acid tert-butyl ester
• 英文别名: Tert-butyl 4-(2-cyclopent-2-en-1-ylethylamino)benzoate；tert-butyl 4-(2-cyclopent-2-en-1-ylethylamino)benzoate
• CAS: 861104-09-8
• 化学式: C₁₈H₂₅NO₂
• 分子量: 287.402
• InChiKey: VCFFDEXVCOFPJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[2-(cyclopent-2-enyl)ethylamino]benzoic acid tert-butyl ester 、 对溴甲苯 在 tris(dibenzylideneacetone)dipalladium (0) 、 sodium t-butanolate 、 2-二苯基磷-2'-(N,N-二甲氨基)联苯 作用下， 以 甲苯 为溶剂， 以74%的产率得到(+/-)-(3aRS,6SR,6aSR)-4-(6-p-tolyloctahydrocyclopenta[b]pyrrol-1-yl)benzoic acd tert-butyl ester
  参考文献：
  名称：

  Selective Synthesis of 5- or 6-Aryl Octahydrocyclopenta[b]pyrroles from a Common Precursor through Control of Competing Pathways in a Pd-Catalyzed Reaction

  摘要：

  The Pd/phosphine-catalyzed reaction of 1 with aryl bromides leads to the selective synthesis of either 6-aryl octahydrocyclopenta[b]pyrroles (3), the corresponding 5-aryl isomers 5, diarylamine 2, or hexahydrocyclopenta[b]pyrrole 4 depending on the structure of the phosphine ligand. These transformations are effective with a variety of different aryl bromides and provide 3-5 with excellent levels of diastereo-selectivity (dr >= 20:1). The changes in product distribution are believed to derive from the influence of Pd-catalyst structure on the relative rates of reductive elimination, beta-hydride elimination, alkene insertion, and alkene displacement processes in a mechanistically complex reaction. The effect of phosphine ligand structure on product distribution is described in detail, along with analysis of a proposed mechanism for these transformations.

  DOI：

  10.1021/ja0430346
• 作为产物：
  描述：

  2-(2-环戊烯-1-基)乙酰胺 在 lithium aluminium tetrahydride 、 tris(dibenzylideneacetone)dipalladium (0) 、 2-(二叔丁基膦)联苯 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 21.0h， 生成 4-[2-(cyclopent-2-enyl)ethylamino]benzoic acid tert-butyl ester
  参考文献：
  名称：

  Selective Synthesis of 5- or 6-Aryl Octahydrocyclopenta[b]pyrroles from a Common Precursor through Control of Competing Pathways in a Pd-Catalyzed Reaction

  摘要：

  The Pd/phosphine-catalyzed reaction of 1 with aryl bromides leads to the selective synthesis of either 6-aryl octahydrocyclopenta[b]pyrroles (3), the corresponding 5-aryl isomers 5, diarylamine 2, or hexahydrocyclopenta[b]pyrrole 4 depending on the structure of the phosphine ligand. These transformations are effective with a variety of different aryl bromides and provide 3-5 with excellent levels of diastereo-selectivity (dr >= 20:1). The changes in product distribution are believed to derive from the influence of Pd-catalyst structure on the relative rates of reductive elimination, beta-hydride elimination, alkene insertion, and alkene displacement processes in a mechanistically complex reaction. The effect of phosphine ligand structure on product distribution is described in detail, along with analysis of a proposed mechanism for these transformations.

  DOI：

  10.1021/ja0430346

文献信息

• Selective Synthesis of 5- or 6-Aryl Octahydrocyclopenta[<i>b</i>]pyrroles from a Common Precursor through Control of Competing Pathways in a Pd-Catalyzed Reaction
  作者：Joshua E. Ney、John P. Wolfe

  DOI：10.1021/ja0430346

  日期：2005.6.1

  The Pd/phosphine-catalyzed reaction of 1 with aryl bromides leads to the selective synthesis of either 6-aryl octahydrocyclopenta[b]pyrroles (3), the corresponding 5-aryl isomers 5, diarylamine 2, or hexahydrocyclopenta[b]pyrrole 4 depending on the structure of the phosphine ligand. These transformations are effective with a variety of different aryl bromides and provide 3-5 with excellent levels of diastereo-selectivity (dr >= 20:1). The changes in product distribution are believed to derive from the influence of Pd-catalyst structure on the relative rates of reductive elimination, beta-hydride elimination, alkene insertion, and alkene displacement processes in a mechanistically complex reaction. The effect of phosphine ligand structure on product distribution is described in detail, along with analysis of a proposed mechanism for these transformations.