3-benzenesulfonyl-4-(3-cyclopentyloxy-4-methoxyphenyl)-1-(2,4,6-trimethylbenzyl)pyrrolidin-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 3-benzenesulfonyl-4-(3-cyclopentyloxy-4-methoxyphenyl)-1-(2,4,6-trimethylbenzyl)pyrrolidin-2-one
• 英文别名: (3R,4S)-3-(benzenesulfonyl)-4-(3-cyclopentyloxy-4-methoxyphenyl)-1-[(2,4,6-trimethylphenyl)methyl]pyrrolidin-2-one
• 化学式: C₃₂H₃₇NO₅S
• 分子量: 547.715
• InChiKey: AWMKISPZYISCBK-GRKNLSHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  39
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  81.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-benzenesulfonyl-4-(3-cyclopentyloxy-4-methoxyphenyl)-1-(2,4,6-trimethylbenzyl)pyrrolidin-2-one 在 氨 、 lithium 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到咯利普兰
  参考文献：
  名称：

  γ-Lactam Synthesis via C−H Insertion:  Elaboration of N-Benzyl Protecting Groups for High Regioselectivity toward the Total Synthesis of Rolipram

  摘要：

  By intramolecular C-H Insertion of alpha-diazo-alpha-(phenylsulfonyl)acetamides, gamma-lactams such as the antidepressant agent rolipram were efficiently synthesized in a highly regioselective manner. N-Benzyl moieties were elaborated as amide protecting groups to enhance regioselectivity in C-H activation as well as chemoselectivity over addition reactions.

  DOI：

  10.1021/ol0345834
• 作为产物：
  描述：

  2-(3-环戊氧基-4-甲氧基苯基)乙胺 在 dirhodium tetraacetate 、 sodium tetrahydroborate 、 4-乙酰氨基苯磺酰叠氮 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 sodium sulfate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 15.5h， 生成 3-benzenesulfonyl-4-(3-cyclopentyloxy-4-methoxyphenyl)-1-(2,4,6-trimethylbenzyl)pyrrolidin-2-one
  参考文献：
  名称：

  γ-Lactam Synthesis via C−H Insertion:  Elaboration of N-Benzyl Protecting Groups for High Regioselectivity toward the Total Synthesis of Rolipram

  摘要：

  By intramolecular C-H Insertion of alpha-diazo-alpha-(phenylsulfonyl)acetamides, gamma-lactams such as the antidepressant agent rolipram were efficiently synthesized in a highly regioselective manner. N-Benzyl moieties were elaborated as amide protecting groups to enhance regioselectivity in C-H activation as well as chemoselectivity over addition reactions.

  DOI：

  10.1021/ol0345834

文献信息

• γ-Lactam Synthesis via C−H Insertion:  Elaboration of <i>N</i>-Benzyl Protecting Groups for High Regioselectivity toward the Total Synthesis of Rolipram
  作者：Cheol Hwan Yoon、Advait Nagle、Chiliu Chen、Drashti Gandhi、Kyung Woon Jung

  DOI：10.1021/ol0345834

  日期：2003.6.1

  By intramolecular C-H Insertion of alpha-diazo-alpha-(phenylsulfonyl)acetamides, gamma-lactams such as the antidepressant agent rolipram were efficiently synthesized in a highly regioselective manner. N-Benzyl moieties were elaborated as amide protecting groups to enhance regioselectivity in C-H activation as well as chemoselectivity over addition reactions.