N-[5-(phenylsulfonyl)penta-3,4-dienyl]-N-[3-(trimethylsilyl)propyn-2-yl]-(4-methylbenzene)sulfonamide | 943734-07-4

• 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-[5-(phenylsulfonyl)penta-3,4-dienyl]-N-[3-(trimethylsilyl)propyn-2-yl]-(4-methylbenzene)sulfonamide
• CAS: 943734-07-4
• 化学式: C₂₄H₂₉NO₄S₂Si
• 分子量: 487.716
• InChiKey: QBZHEWNWBKERAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  88.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[5-(phenylsulfonyl)penta-3,4-dienyl]-N-[3-(trimethylsilyl)propyn-2-yl]-(4-methylbenzene)sulfonamide 、 一氧化碳 在 di(rhodium)tetracarbonyl dichloride 作用下， 以 xylene 为溶剂， 反应 4.0h， 以35%的产率得到N-[4-(methylbenzene)sulfonyl]-10-(phenylsulfonyl)-8-(trimethylsilyl)-5-azabicyclo[5.3.0]deca-1,7-dien-9-one
  参考文献：
  名称：

  Rh(I)-catalyzed Pauson–Khand reaction of 1-phenylsulfonyl-1,2-octadien-7-yne derivatives

  摘要：

  The Rh(I)-catalyzed PKR of 1-phenylsulfonyl- 1,2-octadien-7-ynes and their aza derivatives exclusively produced the corresponding 9-phenylsulfonylbicyclo[4.3.0]nona-1,6-dien-8-ones and no 4-(phenylsulfonylmethylidene)bicyclo [3.3. 0]oct-1-en-3-ones could be detected. Thus, the ring-closing pattern was found to be the same as those of the previously reported 3-phenylsulfonyl-1,2-octadien-7-yne derivatives. However, the formation of 4-(phenylsulfonylmethylidene)-7-oxabicyclo[3.3.0]oct-1-en-3-ones was observed as a minor product when the 5-oxa congeners were used. In addition, a larger ring-sized product, 10-phenylsulfonyl-5-azabicyclo[5.3.0]deca-1,7-dien-9-one derivative, was obtained from the 6-aza derivative of 1-phenylsulfonyl-1,2-nonadien-8-yne. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.04.005
• 作为产物：
  描述：

  5-((tert-butyldimethylsilyl)oxy)pent-1-yn-3-ol 在 偶氮二甲酸二异丙酯 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 对甲苯磺酸 、 三乙胺 、 间氯过氧苯甲酸 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 N-[5-(phenylsulfonyl)penta-3,4-dienyl]-N-[3-(trimethylsilyl)propyn-2-yl]-(4-methylbenzene)sulfonamide
  参考文献：
  名称：

  Rh(I)-catalyzed Pauson–Khand reaction of 1-phenylsulfonyl-1,2-octadien-7-yne derivatives

  摘要：

  The Rh(I)-catalyzed PKR of 1-phenylsulfonyl- 1,2-octadien-7-ynes and their aza derivatives exclusively produced the corresponding 9-phenylsulfonylbicyclo[4.3.0]nona-1,6-dien-8-ones and no 4-(phenylsulfonylmethylidene)bicyclo [3.3. 0]oct-1-en-3-ones could be detected. Thus, the ring-closing pattern was found to be the same as those of the previously reported 3-phenylsulfonyl-1,2-octadien-7-yne derivatives. However, the formation of 4-(phenylsulfonylmethylidene)-7-oxabicyclo[3.3.0]oct-1-en-3-ones was observed as a minor product when the 5-oxa congeners were used. In addition, a larger ring-sized product, 10-phenylsulfonyl-5-azabicyclo[5.3.0]deca-1,7-dien-9-one derivative, was obtained from the 6-aza derivative of 1-phenylsulfonyl-1,2-nonadien-8-yne. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.04.005