8,10-dimethoxyphenanthridine-4-carboxylic acid | 1166398-80-6

• 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: 8,10-dimethoxyphenanthridine-4-carboxylic acid
• 英文别名: 8,10-Dimethoxyphenanthridine-4-carboxylic acid
• CAS: 1166398-80-6
• 化学式: C₁₆H₁₃NO₄
• 分子量: 283.284
• InChiKey: JVKLGRIFONUFFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  68.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  9,11-dimethoxyisoxazolo[4,3,2-de]phenanthridin-4(7H)-one 以 氘代氯仿 为溶剂， 反应 288.0h， 生成 8,10-dimethoxyphenanthridine-4-carboxylic acid
  参考文献：
  名称：

  Synthesis of the Isoxazolo[4,3,2-de]phenanthridinone Moiety of the Parnafungins

  摘要：

  A practical route to the labile tetracyclic isoxazolo[4,3,2-de]phenanthridinone moiety of the antifungal parnafungins has been developed. Zinc reduction of a methyl 2'-hydroxymethyl-2-nitro-3-biphenylcarboxylate, which was prepared by a Suzuki coupling, afforded a benzisoxazolone that was treated with MsCl and base to generate the labile tetracyclic ring system in 37-47% yield. This compound decomposes to the phenanthridine in CDCl3 and the phenanthridine N-oxide in aqueous base.

  DOI：

  10.1021/ol901054r

文献信息

• Synthesis of the Isoxazolo[4,3,2-<i>de</i>]phenanthridinone Moiety of the Parnafungins
  作者：Quan Zhou、Barry B. Snider

  DOI：10.1021/ol901054r

  日期：2009.7.2

  A practical route to the labile tetracyclic isoxazolo[4,3,2-de]phenanthridinone moiety of the antifungal parnafungins has been developed. Zinc reduction of a methyl 2'-hydroxymethyl-2-nitro-3-biphenylcarboxylate, which was prepared by a Suzuki coupling, afforded a benzisoxazolone that was treated with MsCl and base to generate the labile tetracyclic ring system in 37-47% yield. This compound decomposes to the phenanthridine in CDCl3 and the phenanthridine N-oxide in aqueous base.
• Synthesis of Hexacyclic Parnafungin A and C Models
  作者：Quan Zhou、Barry B. Snider

  DOI：10.1021/jo101826p

  日期：2010.12.3

  A convergent, practical route to unstable hexacyclic parnafungin A and C models has been developed. Two iodoxanthones were prepared in four or five steps (33-50% overall yield). Suzuki-Miyaura coupling of the iodoxanthones with excess readily available 3-carbomethoxy-2-nitrophenyl pinacol boronate afforded the hindered highly functionalized 2-arylxanthones (53-58%) in the first key step. In the second key step, zinc reduction gave benzisoxazolinones that were treated with MsCl and then base to generate the unstable hexacyclic parnafungin A (13% overall yield for 8 steps) and C (8% overall yield for 9 steps) models. Analogously to the parnafungins, hexacyclic parnafungin C model decomposes to a phenanthridine with a half-life of 2 d in CDCI3.