(R)-methyl 2-(4-bromophenyl)-1-tosyl-2,5-dihydro-1H-pyrrole-3-carboxylate | 1330067-13-4

• 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: (R)-methyl 2-(4-bromophenyl)-1-tosyl-2,5-dihydro-1H-pyrrole-3-carboxylate
• 英文别名: methyl (2R)-2-(4-bromophenyl)-1-(4-methylphenyl)sulfonyl-2,5-dihydropyrrole-3-carboxylate
• CAS: 1330067-13-4
• 化学式: C₁₉H₁₈BrNO₄S
• 分子量: 436.326
• InChiKey: ZQZYVADTALEXDY-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl 2-((N-allyl-4-methylphenylsulfonamido)(4-bromophenyl)methyl)acrylate 在 Zhan 1-B 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (R)-methyl 2-(4-bromophenyl)-1-tosyl-2,5-dihydro-1H-pyrrole-3-carboxylate 、 (S)-methyl 2-(4-bromophenyl)-1-tosyl-2,5-dihydro-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  Asymmetric Organocatalytic Allylic Substitution of Morita–Baylis–Hillman Carbonates with Allylamines for the Synthesis of 2,5-Dihydropyrroles

  摘要：

  The asymmetric allylic substitution reaction of MBH carbonates with allylamines has been developed, which affords N-allyl-beta-amino-alpha-methylene esters in high yields and enantioselectivities. After a subsequent ring-closure metathesis of the products, a series of optically active 2,5-dihydropyrroles could be obtained smoothly in high yields without any loss of enantioselectivity. Finally, a tentative mechanism for rationalization of the reaction has been proposed.

  DOI：

  10.1021/jo2011522