5-iodo-7-methyl-1,1-diphenyl-3,4-dihydro-1H-[1,3]oxazino[3,4-a]indole | 1027224-12-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: 5-iodo-7-methyl-1,1-diphenyl-3,4-dihydro-1H-[1,3]oxazino[3,4-a]indole
• 英文别名: 5-Iodo-7-methyl-1,1-diphenyl-3,4-dihydro-[1,3]oxazino[3,4-a]indole
• CAS: 1027224-12-9
• 化学式: C₂₄H₂₀INO
• 分子量: 465.333
• InChiKey: LJKFDEBTIWQFER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  14.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-碘-4-甲基苯胺 在 bis-triphenylphosphine-palladium(II) chloride 、 N-碘代丁二酰亚胺 、 copper(l) iodide 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 49.0h， 生成 5-iodo-7-methyl-1,1-diphenyl-3,4-dihydro-1H-[1,3]oxazino[3,4-a]indole
  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

• 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.