methyl 5-methyl-6-oxo-5,6-dihydrophenanthridine-2-carboxylate | 31601-80-6

• 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: methyl 5-methyl-6-oxo-5,6-dihydrophenanthridine-2-carboxylate
• 英文别名: Methyl 5-methyl-6-oxophenanthridine-2-carboxylate
• CAS: 31601-80-6
• 化学式: C₁₆H₁₃NO₃
• 分子量: 267.284
• InChiKey: QINZHRTXUCESJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 5-methyl-6-oxo-5,6-dihydrophenanthridine-2-carboxylate 在 ammonium hydroxide 、 水 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-methyl-6-oxo-5,6-dihydrophenanthridine-2-carboxamide
  参考文献：
  名称：

  Phenanthridin-6-one derivatives as the first class of non-steroidal pharmacological chaperones for Niemann-Pick disease type C1 protein

  摘要：

  Niemann-Pick disease type C is a fatal, progressive neurodegenerative disease mostly caused by mutations in Nieamnn-Pick type C1 (NPC1), a late endosomal membrane protein that is essential for intracellular cholesterol transport. The most prevalent mutation, I1061T (Ile to Thr), interferes with the protein folding process. Consequently, mutated but intrinsically functional NPC1 proteins are prematurely degraded via proteasome, leading to loss of NPC1 function. Previously, we reported sterol derivatives as pharmacological chaperones for NPC1, and showed that these derivatives can normalize folding-defective phenotypes of I1061T NPC1 mutant by directly binding to, and stabilizing, the protein. Here, we report a series of compounds containing a phenanthridin-6-one scaffold as the first class of non-steroidal pharmacological chaperones for NPC1. We also examined their structure-activity relationships. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.04.062
• 作为产物：
  描述：

  4-(anthraniloyl-methyl-amino)-benzoic acid methyl ester 在 硫酸 、 铜 作用下， 生成 methyl 5-methyl-6-oxo-5,6-dihydrophenanthridine-2-carboxylate
  参考文献：
  名称：

  核间环化。第九部分 含邻位取代基的2-氨基-N-甲基苯甲腈的异常反应

  摘要：

  DOI：

  10.1039/jr9540002471

文献信息

• N-Heterocyclic Nitreniums Can Be Employed as Photoredox Catalysts for the Single-Electron Reduction of Aryl Halides
  作者：Kun-Quan Chen、Bei-Bei Zhang、Zhi-Xiang Wang、Xiang-Yu Chen

  DOI：10.1021/acs.orglett.2c01702

  日期：2022.7.1

  nitrenium (NHN) salts, the analogues of N-heterocyclic carbenes, have attracted considerable interest. However, relatively little is known about their catalytic ability beyond their Lewis acid catalysis. Herein, we describe that NHNs can serve as catalytic electron acceptors for charge transfer complex photoactivations. We showcase that, under blue light irradiation, the NHN salts could catalyze the

  N-杂环氮 (NHN) 盐是 N-杂环卡宾的类似物，引起了相当大的兴趣。然而，对于它们在路易斯酸催化之外的催化能力知之甚少。在这里，我们描述了 NHNs 可以作为电荷转移复合物光活化的催化电子受体。我们展示了在蓝光照射下，NHN盐可以催化芳基卤化物生成芳基自由基。
• Synthesis of Heterocycles via Palladium-Catalyzed C-H Activation/Cyclization of Diazonium Salts (Part III): Phenanthridin-6-(5H)-ones
  作者：Zhen-Ting Du、Pan Han、Jing Zhou、Cong-Cong Zhang、Ke Chen

  DOI：10.3987/com-14-13051

  日期：——

  A series of phenanthridin-6-(5H)-ones were synthesized through a palladium-catalyzed C-H activation/cyclization strategy using diazonium salts in good yields. The best conditions included Pd(OAc)(2) as the catalyst, PPh3 as the ligand, toluene as the solvent, K2CO3 as the base and 60 degrees C as the optimal temperature.