methyl 2-(3-chloro-1,4-dimethoxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)acetate | 1443209-63-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: methyl 2-(3-chloro-1,4-dimethoxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)acetate
• 英文别名: methyl 2-(3-chloro-1,4-dimethoxy-9,10-dioxoanthracen-2-yl)acetate
• CAS: 1443209-63-9
• 化学式: C₁₉H₁₅ClO₆
• 分子量: 374.777
• InChiKey: ZMDVPNGZEBJBGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-(3-chloro-1,4-dimethoxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)acetate 在 盐酸 、 copper chromite 、 copper(l) iodide 、 水 、 铜 、 sodium hydride 、 sodium carbonate 作用下， 以 喹啉 、 N,N-二甲基乙酰胺 、 溶剂黄146 、 mineral oil 为溶剂， 反应 11.67h， 生成 4,11-dimethoxyanthra[2,3-b]furan-5,10-dione
  参考文献：
  名称：

  Heterocyclic analogs of 5,12-naphthacene-quinone. 11*. A new method for preparing 4,11-dimethoxyanthra[2,3-b]furan-5,10-dione

  摘要：

  A new method was developed for the synthesis of 4,11-dimethoxyanthra[2,3-b]furan-5,10-dione and some of its previously unknown derivatives. The method was based on heterocyclization of 2-(3-halo-anthraquinon-2-yl)formylacetic acid derivatives by the action of bases, leading to methyl 4,11-dimethoxy-5,10-dioxoanthra[2,3-b]furan-3-carboxylate. Subsequent acid hydrolysis of the ester group and decarboxylation of the obtained acid gave 4,11-dimethoxyanthra[2,3-b]furan-5,10-dione. The low yield of the target compound was probably due to heterocycle instability in the 5,10-dioxo-anthra[2,3-b]furan-3-carboxylic acid derivatives in basic medium.

  DOI：

  10.1007/s10593-013-1240-2
• 作为产物：
  描述：

  methyl 2-(3-chloro-1,4-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)acetate 、 碘甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 2.0h， 以60%的产率得到methyl 2-(3-chloro-1,4-dimethoxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)acetate
  参考文献：
  名称：

  Heterocyclic analogs of 5,12-naphthacene-quinone. 11*. A new method for preparing 4,11-dimethoxyanthra[2,3-b]furan-5,10-dione

  摘要：

  A new method was developed for the synthesis of 4,11-dimethoxyanthra[2,3-b]furan-5,10-dione and some of its previously unknown derivatives. The method was based on heterocyclization of 2-(3-halo-anthraquinon-2-yl)formylacetic acid derivatives by the action of bases, leading to methyl 4,11-dimethoxy-5,10-dioxoanthra[2,3-b]furan-3-carboxylate. Subsequent acid hydrolysis of the ester group and decarboxylation of the obtained acid gave 4,11-dimethoxyanthra[2,3-b]furan-5,10-dione. The low yield of the target compound was probably due to heterocycle instability in the 5,10-dioxo-anthra[2,3-b]furan-3-carboxylic acid derivatives in basic medium.

  DOI：

  10.1007/s10593-013-1240-2

文献信息

• β-Hydroxylation of anthraquinone derivatives with benzaldehyde oxime as a source of hydroxyl group
  作者：Alexander S. Tikhomirov、Ivan V. Ivanov、Alexander M. Korolev、Andrey E. Shchekotikhin

  DOI：10.1016/j.tet.2019.130623

  日期：2019.10

  anthraquinone derivatives that can be used during late stages of modifications. The scheme is based on the Miller-Loudon-Snyder reaction, which uses benzaldoxime as a source of a hydroxyl group. The influence of different leaving groups and neighboring substituents at the anthraquinone core on reaction rate and yield has been evaluated. A series of β-hydroxyanthraquinone derivatives was synthesized

  羟基对蒽醌具有广泛的生物活性，着色特性和合成应用，因此备受关注。在这里，我们描述了一种温和且方便的蒽醌衍生物β-羟基化方法，该方法可用于修饰的后期阶段。该方案基于Miller-Loudon-Snyder反应，该反应使用苯甲醛肟作为羟基来源。评估了蒽醌核心上不同的离去基团和相邻的取代基对反应速率和产率的影响。使用开发的方法合成了一系列β-羟基蒽醌衍生物。