N-benzyl-N-[1-(1,3-cyclohexadienyl)-propan-2-yl] vinylsulfonamide | 265116-08-3

• 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: N-benzyl-N-[1-(1,3-cyclohexadienyl)-propan-2-yl] vinylsulfonamide
• 英文别名: N-benzyl-N-(1-cyclohexa-1,3-dien-1-ylpropan-2-yl)ethenesulfonamide
• CAS: 265116-08-3
• 化学式: C₁₈H₂₃NO₂S
• 分子量: 317.452
• InChiKey: XVCVUKNENOGPIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  N-benzyl-N-[1-(1,3-cyclohexadienyl)-propan-2-yl] vinylsulfonamide 在 2,6-二叔丁基-4-甲基苯酚 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 (1R*,2S*,4S*,2'S*)-N-benzyl-1-propylbicyclo[2.2.2]oct-5-ene-2,2'-sultam 、 (1S*,2R*,4R*,2'S*)-N-benzyl-1-propylbicyclo[2.2.2]oct-5-ene-2,2'-sultam
  参考文献：
  名称：

  High Pressure Intramolecular Diels–Alder Reactions of Vinylsulfonates and Vinylsulfonamides

  摘要：

  Acceleration of the intramolecular Diels-Alder reaction of vinylsulfonic esters and amides bearing acyclic and carbocyclic 1,3-diene moieties by application of high pressure leads to excellent yields of sultones and sultams, respectively, at ambient temperature. The influence of pressure on the stereoselectivity of these processes has been investigated. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)01073-x
• 作为产物：
  描述：

  1-(1,3-cyclohexadienyl)-propan-2-yl 在 吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 61.0h， 生成 N-benzyl-N-[1-(1,3-cyclohexadienyl)-propan-2-yl] vinylsulfonamide
  参考文献：
  名称：

  High Pressure Intramolecular Diels–Alder Reactions of Vinylsulfonates and Vinylsulfonamides

  摘要：

  Acceleration of the intramolecular Diels-Alder reaction of vinylsulfonic esters and amides bearing acyclic and carbocyclic 1,3-diene moieties by application of high pressure leads to excellent yields of sultones and sultams, respectively, at ambient temperature. The influence of pressure on the stereoselectivity of these processes has been investigated. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)01073-x

文献信息

• High Pressure Intramolecular Diels–Alder Reactions of Vinylsulfonates and Vinylsulfonamides
  作者：Bernd Plietker、Dieter Seng、Roland Fröhlich、Peter Metz

  DOI：10.1016/s0040-4020(99)01073-x

  日期：2000.2

  Acceleration of the intramolecular Diels-Alder reaction of vinylsulfonic esters and amides bearing acyclic and carbocyclic 1,3-diene moieties by application of high pressure leads to excellent yields of sultones and sultams, respectively, at ambient temperature. The influence of pressure on the stereoselectivity of these processes has been investigated. (C) 2000 Elsevier Science Ltd. All rights reserved.