1-(phenylsulfonyl)octa-1,2-dien-7-yne | 943733-96-8

• 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: 1-(phenylsulfonyl)octa-1,2-dien-7-yne
• CAS: 943733-96-8
• 化学式: C₁₄H₁₄O₂S
• 分子量: 246.33
• InChiKey: ICQHRPPMHALUMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  1-(phenylsulfonyl)octa-1,2-dien-7-yne 在 bis-triphenylphosphine-palladium(II) chloride 、 di(rhodium)tetracarbonyl dichloride copper(l) iodide 、 二异丙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 1.0h， 生成 7-phenyl-9-(phenylsulfonyl)bicyclo[4.3.0]nona-1,6-dien-8-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：

  octa-1,7-diyn-3-ol 在 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 1-(phenylsulfonyl)octa-1,2-dien-7-yne
  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