(1R,6S)-8-Thia-1-aza-bicyclo[4.2.1]non-4-ene 8,8-dioxide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吖庚因类
• 英文名称: (1R,6S)-8-Thia-1-aza-bicyclo[4.2.1]non-4-ene 8,8-dioxide
• 英文别名: (6S)-8lambda6-thia-1-azabicyclo[4.2.1]non-4-ene 8,8-dioxide；(6S)-8λ6-thia-1-azabicyclo[4.2.1]non-4-ene 8,8-dioxide
• 化学式: C₇H₁₁NO₂S
• 分子量: 173.236
• InChiKey: BYNLOQZZHWLICS-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,6S)-8-Thia-1-aza-bicyclo[4.2.1]non-4-ene 8,8-dioxide 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以58%的产率得到(1S,6S)-3-Bromo-8-thia-1-aza-bicyclo[4.2.1]non-4-ene 8,8-dioxide
  参考文献：
  名称：

  Synthesis of 1-Aza-8-thiabicyclo[4.2.1]nona-2,4-diene 8,8-Dioxide and Its Conversion to a Strained Spirocycle via Photoinduced SO₂−N Bond Cleavage

  摘要：

  A route to the doubly unsaturated bridgehead sultam 12 has been developed. When irradiated at 350 nm, this conjugated diene is isomerized via a two-photon process to the structurally novel spiro heterocycle 17 constituted of cyclobutene, thietane dioxide, and pyrrolidine rings. A probable mechanism for the generation of 17 and select reactions thereof are reported.

  DOI：

  10.1021/ol049679s
• 作为产物：
  描述：

  1-Bromomethanesulfonyl-2,3,4,7-tetrahydro-1H-azepine 在 palladium diacetate 三(2-呋喃基)膦 、 4 A molecular sieve 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以67%的产率得到(1R,6S)-8-Thia-1-aza-bicyclo[4.2.1]non-4-ene 8,8-dioxide
  参考文献：
  名称：

  Synthesis of 1-Aza-8-thiabicyclo[4.2.1]nona-2,4-diene 8,8-Dioxide and Its Conversion to a Strained Spirocycle via Photoinduced SO₂−N Bond Cleavage

  摘要：

  A route to the doubly unsaturated bridgehead sultam 12 has been developed. When irradiated at 350 nm, this conjugated diene is isomerized via a two-photon process to the structurally novel spiro heterocycle 17 constituted of cyclobutene, thietane dioxide, and pyrrolidine rings. A probable mechanism for the generation of 17 and select reactions thereof are reported.

  DOI：

  10.1021/ol049679s

文献信息

• Synthesis of 1-Aza-8-thiabicyclo[4.2.1]nona-2,4-diene 8,8-Dioxide and Its Conversion to a Strained Spirocycle via Photoinduced SO₂−N Bond Cleavage
  作者：Leo A. Paquette、William R. S. Barton、Judith C. Gallucci

  DOI：10.1021/ol049679s

  日期：2004.4.1

  A route to the doubly unsaturated bridgehead sultam 12 has been developed. When irradiated at 350 nm, this conjugated diene is isomerized via a two-photon process to the structurally novel spiro heterocycle 17 constituted of cyclobutene, thietane dioxide, and pyrrolidine rings. A probable mechanism for the generation of 17 and select reactions thereof are reported.