2-<3-(phenylsulfonyl)-3-butenyl>-1-bromobenzene | 129855-22-7

• 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-(phenylsulfonyl)-3-butenyl>-1-bromobenzene
• 英文别名: 1-[3-(Benzenesulfonyl)but-3-en-1-yl]-2-bromobenzene；1-[3-(benzenesulfonyl)but-3-enyl]-2-bromobenzene
• CAS: 129855-22-7
• 化学式: C₁₆H₁₅BrO₂S
• 分子量: 351.264
• InChiKey: SYZYSELJNFJCJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-<3-(phenylsulfonyl)-3-butenyl>-1-bromobenzene 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 以88%的产率得到2-(phenylsulfonyl)-1,2,3,4-tetrahydronaphthalene
  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
• 作为产物：
  描述：

  3-(phenylsulfonyl)-2-(phenylthio)-1-propene 在 偶氮二异丁腈 、 双氧水 、 三正丁基氢锡 、 溶剂黄146 作用下， 以 苯 为溶剂， 生成 2-<3-(phenylsulfonyl)-3-butenyl>-1-bromobenzene
  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

• Synthesis of vinylic and cyclic sulfones via a radical addition-elimination sequence
  作者：Albert Padwa、S.Shaun Murphree、Philip E. Yeske

  DOI：10.1016/s0040-4039(00)89004-8

  日期：——
• PADWA, ALBERT;MURPHREE, G. SHAUN;YESKE, PHILIP E., TETRAHEDRON LETT., 31,(1990) N1, C. 2983-2986
  作者：PADWA, ALBERT、MURPHREE, G. SHAUN、YESKE, PHILIP E.

  DOI：——

  日期：——
• 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.