2-benzenesulfonyl-N-[2-(3-cyclopentyloxy-4-methoxyphenyl)ethyl]-2-diazo-N-(2,4,6-trimethylbenzyl)acetamide | 569342-91-2

• 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: 2-benzenesulfonyl-N-[2-(3-cyclopentyloxy-4-methoxyphenyl)ethyl]-2-diazo-N-(2,4,6-trimethylbenzyl)acetamide
• 英文别名: 2-(benzenesulfonyl)-N-[2-(3-cyclopentyloxy-4-methoxyphenyl)ethyl]-2-diazo-N-[(2,4,6-trimethylphenyl)methyl]acetamide
• CAS: 569342-91-2
• 化学式: C₃₂H₃₇N₃O₅S
• 分子量: 575.729
• InChiKey: BKJZBPSPGFSYIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  83.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-benzenesulfonyl-N-[2-(3-cyclopentyloxy-4-methoxyphenyl)ethyl]-2-diazo-N-(2,4,6-trimethylbenzyl)acetamide 在 dirhodium tetraacetate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 以75%的产率得到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
• 作为产物：
  描述：

  N-(3-(cyclopentyloxy)-4-methoxyphenethyl)-2-(phenylsulfonyl)-N-(2,4,6-trimethylbenzyl)acetamide 在 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 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成 2-benzenesulfonyl-N-[2-(3-cyclopentyloxy-4-methoxyphenyl)ethyl]-2-diazo-N-(2,4,6-trimethylbenzyl)acetamide
  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

• Org. Lett. 2003, 5, 2259-2262
  作者：

  DOI：——

  日期：——