(3E)-5-(3aRS,7aRS)-1,2,7,7a-tetrahydro-1-(toluene-4-sulfonyl)-3aH-indol-3((6H)-ylidene)pentan-2-one

• 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: (3E)-5-(3aRS,7aRS)-1,2,7,7a-tetrahydro-1-(toluene-4-sulfonyl)-3aH-indol-3((6H)-ylidene)pentan-2-one
• 英文别名: (5E)-5-[(3aR,7aR)-1-(4-methylphenyl)sulfonyl-3a,6,7,7a-tetrahydro-2H-indol-3-ylidene]pentan-2-one
• 化学式: C₂₀H₂₅NO₃S
• 分子量: 359.489
• InChiKey: RMCAQGQJSJQRRJ-NVBHJRBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  丁烯酮 、 N-(cyclohex-2-en-1-yl)-4-methyl-N-(prop-2-yn-1-yl)benzenesulfonamide 在 三乙胺 bis(triphenylphosphine)nickel(II) chloride 、 zinc(II) chloride 、 锌 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以50%的产率得到(3E)-5-(3aRS,7aRS)-1,2,7,7a-tetrahydro-1-(toluene-4-sulfonyl)-3aH-indol-3((6H)-ylidene)pentan-2-one
  参考文献：
  名称：

  Ni-Catalyzed, ZnCl₂-Assisted Domino Coupling of Enones, Alkynes, and Alkenes

  摘要：

  A Ni(O)/ZnCl2 system effectively promotes the coupling of enones and alkene-tethered alkynes. In the reaction with 1,6-enynes, the oxidative cyclization of Ni(O) species on enones across the alkyne part followed by ZnCl2-promoted cleavage generates alkenylnickel intermediates. Subsequent migratory insertion of the tethered alkene occurs with 5-exo-cyclization. When the resulting sigma-alkylnickel intermediates have beta-hydrogen atoms, the reaction terminates by beta-hydrogen elimination to provide cyclopentane derivatives. On the other hand, a sigma-alkylnickel intermediate that does not have beta-hydrogen atoms undergoes the insertion of a second alkene unit to cause a domino effect via a three-fold C-C bond formation process with and without the cleavage of one C-C bond.

  DOI：

  10.1021/ja047580a

文献信息

• Ni-Catalyzed, ZnCl₂-Assisted Domino Coupling of Enones, Alkynes, and Alkenes
  作者：Shin-ichi Ikeda、Reiko Sanuki、Hiroko Miyachi、Hitoshi Miyashita、Masami Taniguchi、Kazunori Odashima

  DOI：10.1021/ja047580a

  日期：2004.8.1

  A Ni(O)/ZnCl2 system effectively promotes the coupling of enones and alkene-tethered alkynes. In the reaction with 1,6-enynes, the oxidative cyclization of Ni(O) species on enones across the alkyne part followed by ZnCl2-promoted cleavage generates alkenylnickel intermediates. Subsequent migratory insertion of the tethered alkene occurs with 5-exo-cyclization. When the resulting sigma-alkylnickel intermediates have beta-hydrogen atoms, the reaction terminates by beta-hydrogen elimination to provide cyclopentane derivatives. On the other hand, a sigma-alkylnickel intermediate that does not have beta-hydrogen atoms undergoes the insertion of a second alkene unit to cause a domino effect via a three-fold C-C bond formation process with and without the cleavage of one C-C bond.