(E)-1-phenyl-2-(1-phenylsulfonylindol-3-yl)ethylene | 144646-92-4

• 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: (E)-1-phenyl-2-(1-phenylsulfonylindol-3-yl)ethylene
• 英文别名: 1-(benzenesulfonyl)-3-[(E)-2-phenylethenyl]indole
• CAS: 144646-92-4
• 化学式: C₂₂H₁₇NO₂S
• 分子量: 359.448
• InChiKey: AZDRWDCGPFNUSJ-FOCLMDBBSA-N

物化性质

• 沸点：
  569.4±48.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  47.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1-phenyl-2-(1-phenylsulfonylindol-3-yl)ethylene 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以87%的产率得到(E)-3-styryl-1H-indole
  参考文献：
  名称：

  Palladium-Catalyzed Coupling of 3-Indolyl Triflate. Syntheses of 3-Vinyl and 3-Alkynylindoles

  摘要：

  Palladium-catalyzed coupling of 1 -(phenylsulfonyl)indol-3-yl trifluoromethanesulfonate (triflate) (1) with terminal alkenes and alkenes gives 3-vinyl (2) and 3-alkynylindoles in 45-93% yields. An attempt to generate 2,3-indolyne 22 from 2-trimethylsilyl-3-indolyl triflate 20 gives indigo (23).

  DOI：

  10.1080/00397919208019065
• 作为产物：
  描述：

  苯乙烯 、 1-(phenylsulfonyl)indol-3-yl trifluoromethanesulfonate 在 bis-triphenylphosphine-palladium(II) chloride 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以75%的产率得到(E)-1-phenyl-2-(1-phenylsulfonylindol-3-yl)ethylene
  参考文献：
  名称：

  Palladium-Catalyzed Coupling of 3-Indolyl Triflate. Syntheses of 3-Vinyl and 3-Alkynylindoles

  摘要：

  Palladium-catalyzed coupling of 1 -(phenylsulfonyl)indol-3-yl trifluoromethanesulfonate (triflate) (1) with terminal alkenes and alkenes gives 3-vinyl (2) and 3-alkynylindoles in 45-93% yields. An attempt to generate 2,3-indolyne 22 from 2-trimethylsilyl-3-indolyl triflate 20 gives indigo (23).

  DOI：

  10.1080/00397919208019065

文献信息

• Imaging agents for protein misfolding
  申请人：Wisniewski Thomas

  公开号：US20100279340A1

  公开（公告）日：2010-11-04

  Charged and neutral small fluorescent molecules based upon the styryl scaffold are useful as imaging agents for misfolded proteins such as amyloid plaque. Charged molecules are prepared using pyrrolidine catalyzed reactions by solution-phase synthesis. Neutral styryl molecules are prepared using acetic anhydride catalyzed reactions, Horner-Emmons reactions or Wittig reactions.
• US8158380B2
  申请人：——

  公开号：US8158380B2

  公开（公告）日：2012-04-17
• Palladium-Catalyzed Coupling of 3-Indolyl Triflate. Syntheses of 3-Vinyl and 3-Alkynylindoles
  作者：Gordon W. Gribble、Samuel C. Conway

  DOI：10.1080/00397919208019065

  日期：1992.8

  Palladium-catalyzed coupling of 1 -(phenylsulfonyl)indol-3-yl trifluoromethanesulfonate (triflate) (1) with terminal alkenes and alkenes gives 3-vinyl (2) and 3-alkynylindoles in 45-93% yields. An attempt to generate 2,3-indolyne 22 from 2-trimethylsilyl-3-indolyl triflate 20 gives indigo (23).