5-methyl-6-(1-nitroethyl)-5,6-dihydrobenzo[c]phenanthridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5-methyl-6-(1-nitroethyl)-5,6-dihydrobenzo[c]phenanthridine
• 英文别名: 5-methyl-6-(1-nitroethyl)-6H-benzo[c]phenanthridine
• 化学式: C₂₀H₁₈N₂O₂
• 分子量: 318.375
• InChiKey: KEAKJDYVZGWDKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  49.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-bromo-N-(α-naphthyl)benzylamine 在 C₁₈H₃₃P*BF₃*FH 、 palladium diacetate 、 sodium hydride 、 caesium carbonate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 copper(I) bromide 作用下， 以 四氢呋喃 、 N,N-二甲基乙酰胺 、 甲苯 、 乙腈 、 mineral oil 为溶剂， 反应 46.5h， 生成 5-methyl-6-(1-nitroethyl)-5,6-dihydrobenzo[c]phenanthridine
  参考文献：
  名称：

  Synthesis of N -methyl-5,6-dihydrobenzo[ c ]phenanthridine and its sp 3 C(6)–H bond functionalization via oxidative cross-dehydrogenative coupling reactions

  摘要：

  An expeditious route involving a Pd-catalyzed intramolecular biaryl-coupling for the synthesis of the N-methyl-5,6-dihydrobenzo[c]phenanthridine scaffold has been developed. For the first time, we herein report the sp(3) C(6)-H functionalization of this heterocyclic scaffold through DDQ-mediated cross-dehydrogenative coupling reactions with nitroalkanes, dialkyl malonates, alkynes, dialkyl phosphites, carbonyl compounds, pyrrole, and indoles. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.10.018

文献信息

• Synthesis of N -methyl-5,6-dihydrobenzo[ c ]phenanthridine and its sp 3 C(6)–H bond functionalization via oxidative cross-dehydrogenative coupling reactions
  作者：Adriana Romo-Pérez、Luis D. Miranda、Abraham García

  DOI：10.1016/j.tetlet.2015.10.018

  日期：2015.12

  An expeditious route involving a Pd-catalyzed intramolecular biaryl-coupling for the synthesis of the N-methyl-5,6-dihydrobenzo[c]phenanthridine scaffold has been developed. For the first time, we herein report the sp(3) C(6)-H functionalization of this heterocyclic scaffold through DDQ-mediated cross-dehydrogenative coupling reactions with nitroalkanes, dialkyl malonates, alkynes, dialkyl phosphites, carbonyl compounds, pyrrole, and indoles. (C) 2015 Elsevier Ltd. All rights reserved.