8,9-dimethoxy-4-methylnaphtho[3,2,1-cd]indol-5(4H)-one | 1431885-19-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 8,9-dimethoxy-4-methylnaphtho[3,2,1-cd]indol-5(4H)-one
• CAS: 1431885-19-6
• 化学式: C₁₈H₁₅NO₃
• 分子量: 293.322
• InChiKey: SSACJWORKXPLDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (±)-4-methoxybenzyl 3-(2-bromo-4,5-dimethoxybenzyl)-1-methyl-2-oxoindoline-3-carboxylate 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 12.0h， 以53%的产率得到8,9-dimethoxy-4-methylnaphtho[3,2,1-cd]indol-5(4H)-one
  参考文献：
  名称：

  DDQ-mediated Direct Intramolecular-Dehydrogenative-Coupling (IDC): Expeditious Approach to the Tetracyclic Core of Ergot Alkaloids

  摘要：

  An efficient route to 2-oxindoles bearing an all-carbon quaternary center at the pseudobenzylic position has been developed via a DDQ-mediated Intramolecular-Dehydrogenative-Coupling (IDC). The methodology involves a one-pot C-alkylation of beta-N-arylamido esters (7) concomitant with dehydrogenative-coupling in the presence of stoichiometric amount of DDQ. A tentative mechanistic route has been proposed for the oxidative coupling. The methodology provides a two-step entry to the ergoline structure of ergot alkaloids.

  DOI：

  10.1021/ol400899e

文献信息

• Substrates as Electron-Donor Precursors: Synthesis of Naphtho-Fused Oxindoles via Benzannulation of 2-Halobenzaldehydes and Indolin-2-ones
  作者：Feng-Cheng Jia、Cheng Xu、Zhi-Wen Zhou、Qun Cai、Yan-Dong Wu、An-Xin Wu

  DOI：10.1021/acs.orglett.6b02515

  日期：2016.10.21

  base-promoted homolytic aromatic substitution. This novel cascade reaction provides a straightforward approach toward various naphtho-fused oxindoles from 2-halobenzaldehydes and indolin-2-ones in the presence of Cs2CO3 in DMSO. The enolates of indolin-2-ones as new and internal electron donors have been demonstrated to initiate intramolecular radical dehalogenative coupling.

  通过将分子间的阿道尔顿缩合反应与随后的分子内碱基促进的均相芳族取代反应相结合，已经实现了一种不寻常的苯环化反应。这种新颖的级联反应为在DMSO中存在Cs 2 CO 3的情况下从2-卤代苯甲醛和吲哚-2-酮的各种萘稠合的吲哚提供了直接的方法。吲哚-2-酮作为新的和内部的电子供体的烯醇被证明可以引发分子内自由基脱卤偶联。