4-[2-(Benzylideneamino)phenyl]but-3-yn-1-ol | 1157868-14-8

• 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: 4-[2-(Benzylideneamino)phenyl]but-3-yn-1-ol
• CAS: 1157868-14-8
• 化学式: C₁₇H₁₅NO
• 分子量: 249.312
• InChiKey: GEKIDDPFHDXTFQ-UHFFFAOYSA-N

物化性质

• 沸点：
  465.9±30.0 °C(predicted)
• 密度：
  0.99±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-[2-(Benzylideneamino)phenyl]but-3-yn-1-ol 在 碘 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成 4-phenyl-2,3-dihydrofuro[3,2-c]quinoline
  参考文献：
  名称：

  Alternating Iodonium-Mediated Reaction Cascades Giving Indole- And Quinoline-Containing Polycycles

  摘要：

  A simple two-step convergent protocol gives direct access to synthetic intermediate A from ortho-iodoanilines. Intermediate A can be treated with NIS in CH(2)Cl(2) to induce novel iodonium mediated domino reaction cascade, which provides direct access to ring-fused indole compounds B. Simply by changing the reaction conditions, this protocol can be directed down an alternative domino reaction cascade to give various ring fused quinoline compounds C.

  DOI：

  10.1021/ol800202u
• 作为产物：
  描述：

  苯甲醛 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-[2-(Benzylideneamino)phenyl]but-3-yn-1-ol
  参考文献：
  名称：

  Scaffold-Divergent Synthesis of Ring-Fused Indoles, Quinolines, and Quinolones via Iodonium-Induced Reaction Cascades

  摘要：

  N-(2-lodophenyl)imines A are readily formed from Schiff's base condensation of 2-iodoanilines with carbonyls and ketals. These imines provide useful substrates in scaffold-divergent synthesis through the attachment of an alkyne (Songashira coupling or acyl substitution of a Weinreb amide) followed by an iodonium-induced reaction cascade to give ring-fused indoles B, quinolines C, or quinolones D depending on the reaction conditions employed.

  DOI：

  10.1021/jo400125p

文献信息

• AuCl₃-Catalyzed Tandem Reaction of <i>N</i>-(<i>o</i>-Alkynylphenyl)imines: A Modular Entry to Polycyclic Frameworks Containing an Indole Unit
  作者：Baoming Ji、Weijun Fu、Chen Xu、Guanglong Zou、Dongfeng Hong、Dongsheng Deng、Zhiqiang Wang

  DOI：10.1055/s-0028-1087938

  日期：——

  A highly efficient tandem cyclization reaction of N-(o-alkynylphenyl)imines leading to ring-fused indoles was developed by using gold(III) as a catalyst under extremely mild reaction conditions.

  在极其温和的反应条件下，使用金（III）作为催化剂，N-(邻炔基苯基)亚胺的高效串联环化反应得以实现，并最终形成环状吲哚。
• Alternating Iodonium-Mediated Reaction Cascades Giving Indole- And Quinoline-Containing Polycycles
  作者：Rosliana Halim、Peter J. Scammells、Bernard L. Flynn

  DOI：10.1021/ol800202u

  日期：2008.5.1

  A simple two-step convergent protocol gives direct access to synthetic intermediate A from ortho-iodoanilines. Intermediate A can be treated with NIS in CH(2)Cl(2) to induce novel iodonium mediated domino reaction cascade, which provides direct access to ring-fused indole compounds B. Simply by changing the reaction conditions, this protocol can be directed down an alternative domino reaction cascade to give various ring fused quinoline compounds C.
• Scaffold-Divergent Synthesis of Ring-Fused Indoles, Quinolines, and Quinolones via Iodonium-Induced Reaction Cascades
  作者：Rosliana Halim、Luigi Aurelio、Peter J. Scammells、Bernard L. Flynn

  DOI：10.1021/jo400125p

  日期：2013.5.17

  N-(2-lodophenyl)imines A are readily formed from Schiff's base condensation of 2-iodoanilines with carbonyls and ketals. These imines provide useful substrates in scaffold-divergent synthesis through the attachment of an alkyne (Songashira coupling or acyl substitution of a Weinreb amide) followed by an iodonium-induced reaction cascade to give ring-fused indoles B, quinolines C, or quinolones D depending on the reaction conditions employed.