4-[2-(Benzhydrylideneamino)phenyl]but-3-yn-1-ol | 1157868-10-4

• 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: 4-[2-(Benzhydrylideneamino)phenyl]but-3-yn-1-ol
• CAS: 1157868-10-4
• 化学式: C₂₃H₁₉NO
• 分子量: 325.41
• InChiKey: FKOGXDXESYXHHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 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-(Benzhydrylideneamino)phenyl]but-3-yn-1-ol 在 碘 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以99.1 mg的产率得到4-phenyl-2,3-dihydrofuro[3,2-c]quinoline
  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
• 作为产物：
  描述：

  2-碘苯胺 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 4-[2-(Benzhydrylideneamino)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。
• An efficient synthesis of ring-fused indoles via copper-catalyzed tandem reaction of N-(o-alkynylphenyl)imines
  作者：Weijun Fu、Mei Zhu、Guanglong Zou

  DOI：10.1002/aoc.1648

  日期：——

  A copper‐catalyzed tandem intramolecular cyclization‐addition reaction of N‐(o‐alkynylphenyl)imines is disclosed. This strategy offers a simple and promising method for accessing ring‐fused indoles. Copyright © 2010 John Wiley & Sons, Ltd.

  公开了N-（邻炔基苯基）亚胺的铜催化串联分子内环化加成反应。该策略提供了一种简单而有前途的方法来访问环稠吲哚。版权所有©2010 John Wiley＆Sons，Ltd.
• 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.