2,3,6,7-tetrahydro-2-acetyl-7a-(phenylsulfonyl)-3a,6-epoxyisoindole | 137059-28-0

• 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: 2,3,6,7-tetrahydro-2-acetyl-7a-(phenylsulfonyl)-3a,6-epoxyisoindole
• 英文别名: 1-[5-(Benzenesulfonyl)-10-oxa-3-azatricyclo[5.2.1.01,5]dec-8-en-3-yl]ethanone；1-[5-(benzenesulfonyl)-10-oxa-3-azatricyclo[5.2.1.01,5]dec-8-en-3-yl]ethanone
• CAS: 137059-28-0
• 化学式: C₁₆H₁₇NO₄S
• 分子量: 319.381
• InChiKey: VWAYWEKBZWMWBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,3-双(苯基磺酰基)-1-丙烯 在 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 7.0h， 生成 2,3,6,7-tetrahydro-2-acetyl-7a-(phenylsulfonyl)-3a,6-epoxyisoindole
  参考文献：
  名称：

  Use of 2,3-bis(phenylsulfonyl)-1-propene as a multicoupling reagent

  摘要：

  2,3-Bis(phenylsulfonyl)-1-propene (1) reacts with various amines to afford products derived from addition across the double bond as well as S(N)2' displacement. When treated with 2-piperidinemethanol, bissulfone 1 gave the expected S(N)2' product which was converted to the corresponding bromide and cyclized with tributyltin hydride to a bicyclic amine. Reaction of bissulfone 1 with furfurylamine followed by treatment with acetyl chloride afforded the product derived from a tandem S(N)2' displacement-intramolecular Diels-Alder reaction. Several novel heterocyclic compounds were prepared by connecting two nucleophilic sites with a carbon-carbon bond and allowing this reagent to react with bissulfone 1. The reaction of 1 with the pyrrolidine enamine derived from cyclohexanone gave bicyclo[3.3.1]nonan-9-one in 78% yield. The soft nucleophile approach is not the only way to add carbon centers to bissulfone 1. Radical attack on the double bond of 1 leads to an intermediate sulfonyl-stabilized radical. This species readily fragments to produce a new vinyl sulfone which undergoes further radical cyclization to give six-membered ring sulfones.

  DOI：

  10.1021/jo00027a052

文献信息

• Use of 2,3-bis(phenylsulfonyl)-1-propene as a multicoupling reagent
  作者：Albert Padwa、Donald N. Kline、S. Shaun Murphree、Philip E. Yeske

  DOI：10.1021/jo00027a052

  日期：1992.1

  2,3-Bis(phenylsulfonyl)-1-propene (1) reacts with various amines to afford products derived from addition across the double bond as well as S(N)2' displacement. When treated with 2-piperidinemethanol, bissulfone 1 gave the expected S(N)2' product which was converted to the corresponding bromide and cyclized with tributyltin hydride to a bicyclic amine. Reaction of bissulfone 1 with furfurylamine followed by treatment with acetyl chloride afforded the product derived from a tandem S(N)2' displacement-intramolecular Diels-Alder reaction. Several novel heterocyclic compounds were prepared by connecting two nucleophilic sites with a carbon-carbon bond and allowing this reagent to react with bissulfone 1. The reaction of 1 with the pyrrolidine enamine derived from cyclohexanone gave bicyclo[3.3.1]nonan-9-one in 78% yield. The soft nucleophile approach is not the only way to add carbon centers to bissulfone 1. Radical attack on the double bond of 1 leads to an intermediate sulfonyl-stabilized radical. This species readily fragments to produce a new vinyl sulfone which undergoes further radical cyclization to give six-membered ring sulfones.