(5R,7aR)-5-(3-carbomethoxybenzyl)hexahydropyrrolizin-3-one | 1212022-95-1

• 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: (5R,7aR)-5-(3-carbomethoxybenzyl)hexahydropyrrolizin-3-one
• 英文别名: methyl 3-[[(3R,8R)-5-oxo-1,2,3,6,7,8-hexahydropyrrolizin-3-yl]methyl]benzoate
• CAS: 1212022-95-1
• 化学式: C₁₆H₁₉NO₃
• 分子量: 273.332
• InChiKey: YWZHWEWTYAEXRR-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (R)-(+)-5-but-3-enylpyrrolidin-2-one 、 间氯苯甲酸甲酯 在 tris-(dibenzylideneacetone)dipalladium(0) 、 caesium carbonate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 1,4-二氧六环 为溶剂， 反应 21.5h， 以85%的产率得到(5R,7aR)-5-(3-carbomethoxybenzyl)hexahydropyrrolizin-3-one
  参考文献：
  名称：

  Diastereoselective Synthesis of Hexahydro-3H-pyrrolyzin-3-ones through Pd-Catalyzed Carboamination

  摘要：

  The reaction of readily available (5R)-5-but-3-en-1-ylpyrrolidin-2-one with aryl bromides, chlorides, or triflates in the presence of Pd-2(dba)(3), Xphos, and Cs2CO3 in 1,4-dioxane at 120 degrees C affords (5R,7aR)-5-aryl hexahydropyrrolizidin-3-ones in good to high yields through a diastereoselective carboamination reaction. Aryl iodides are less successful substrates than bromides and chlorides.

  DOI：

  10.1021/jo1002032

文献信息

• Diastereoselective Synthesis of Hexahydro-3<i>H</i>-pyrrolyzin-3-ones through Pd-Catalyzed Carboamination
  作者：Luana Bagnoli、Sandro Cacchi、Giancarlo Fabrizi、Antonella Goggiamani、Catalina Scarponi、Marcello Tiecco

  DOI：10.1021/jo1002032

  日期：2010.3.19

  The reaction of readily available (5R)-5-but-3-en-1-ylpyrrolidin-2-one with aryl bromides, chlorides, or triflates in the presence of Pd-2(dba)(3), Xphos, and Cs2CO3 in 1,4-dioxane at 120 degrees C affords (5R,7aR)-5-aryl hexahydropyrrolizidin-3-ones in good to high yields through a diastereoselective carboamination reaction. Aryl iodides are less successful substrates than bromides and chlorides.