N-(methoxymethyl)carbazole-1,4-quinone | 1316258-47-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: N-(methoxymethyl)carbazole-1,4-quinone
• 英文别名: 9-(Methoxymethyl)carbazole-1,4-dione；9-(methoxymethyl)carbazole-1,4-dione
• CAS: 1316258-47-5
• 化学式: C₁₄H₁₁NO₃
• 分子量: 241.246
• InChiKey: GLKJLIQOWWEPQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  48.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-iodo-1-(methoxymethyl)indole-2-carboxaldehyde 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 氧气 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 28.17h， 生成 N-(methoxymethyl)carbazole-1,4-quinone
  参考文献：
  名称：

  氧气氛下串联闭环复分解和脱氢反应新合成咔唑-1,4-醌及其在合成莫拉基醌A中的应用

  摘要：

  氧气氛下的串联闭环复分解和脱氢反应是新开发的，用于咔唑-1,4-醌的合成。该新的串联反应可通过四个步骤应用于合成墨拉基醌A。

  DOI：

  10.1016/j.tetlet.2011.05.066

文献信息

• A novel one-pot synthesis of carbazole-1,4-quinones through Pd-catalyzed cyclocarbonylation, desilylation and oxidation processes from 3-iodo-2-propenylindoles
  作者：Mami Fujii、Takashi Nishiyama、Tominari Choshi、Nanase Satsuki、Takaya Fujiwaki、Takumi Abe、Minoru Ishikura、Satoshi Hibino

  DOI：10.1016/j.tet.2014.01.015

  日期：2014.3

  novel one-pot synthesis of carbazole-1,4-quinone by consecutive Pd-catalyzed cyclocarbonylation, desilylation, and oxidation reactions is described. We propose a possible mechanism of the cyclocarbonylation reaction between 3-iodo-2-propenylindole and CO (1 atm) in the presence of a tributyl(vinyl)tin and Pd-catalyst and the resulting acylpalladium species was directly coupled with a terminal alkene to produce the carbazole-1,4-quinone. To our knowledge, this is the first example of this type of reaction. A new formal total synthesis of a carbazole-1,4-quinone alkaloid, murrayaquinone A was established using this reaction. (C) 2014 Elsevier Ltd. All rights reserved.
• New synthesis of carbazole-1,4-quinone using a tandem ring-closing metathesis and dehydrogenation reaction under oxygen atmosphere, and its application to the synthesis of murrayaquinone A
  作者：Takashi Nishiyama、Tominari Choshi、Kohdai Kitano、Satoshi Hibino

  DOI：10.1016/j.tetlet.2011.05.066

  日期：2011.7

  A tandem ring-closing metathesis and dehydrogenation reaction under oxygen atmosphere was newly developed to the synthesis of carbazole-1,4-quinones. This new tandem reaction was applied to the synthesis of murrayaquinone A in four steps.

  氧气氛下的串联闭环复分解和脱氢反应是新开发的，用于咔唑-1,4-醌的合成。该新的串联反应可通过四个步骤应用于合成墨拉基醌A。