N-(dimethylaminomethylene)-2-iodoaniline | 53666-10-7

• 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: N-(dimethylaminomethylene)-2-iodoaniline
• 英文别名: N,N-Dimethyl-N'-2-iodphenylformamidin；N-(dimethylaminoethylene)-2-iodoaniline；Methanimidamide, N'-(2-iodophenyl)-N,N-dimethyl-；N'-(2-iodophenyl)-N,N-dimethylmethanimidamide
• CAS: 53666-10-7
• 化学式: C₉H₁₁IN₂
• 分子量: 274.104
• InChiKey: UFGZQSGWCRGMPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  15.6
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(dimethylaminomethylene)-2-iodoaniline 、 苯乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成
  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：

  2-碘苯胺 、 N,N-二甲基甲酰胺二甲基缩醛 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-(dimethylaminomethylene)-2-iodoaniline
  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

文献信息

• 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.
• 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.