2'-(9,10-dimethoxy-3,8-bismethoxymethoxy-2-methoxymethylanthracen-1-yl)-[1',3']-dioxane | 565176-63-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2'-(9,10-dimethoxy-3,8-bismethoxymethoxy-2-methoxymethylanthracen-1-yl)-[1',3']-dioxane
• CAS: 565176-63-8
• 化学式: C₂₆H₃₂O₉
• 分子量: 488.535
• InChiKey: ICBHBILAOUTLFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.56
• 重原子数：
  35.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  83.07
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2'-(9,10-dimethoxy-3,8-bismethoxymethoxy-2-methoxymethylanthracen-1-yl)-[1',3']-dioxane 在 硫酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 72.0h， 以72%的产率得到9,10-dimethoxy-3,8-bismethoxymethoxy-2-methoxymethylanthracene-1-carbaldehyde
  参考文献：
  名称：

  Studies towards the total synthesis of mumbaistatin: synthesis of highly substituted benzophenone and anthraquinone building blocks

  摘要：

  Model compounds and building blocks for a planned total synthesis of the highly potent glucose-6-phosphate (G6P) translocase inhibitor mumbaistatin (1) and structural analogs were elaborated: compound 1 represents a lead structure in the development of potential new antidiabetic drugs. With the model substrate 20 it was demonstrated that highly functionalized, tetra-ortho-substituted benzophenones can be prepared by nucleophilic addition of an aryllithium-building block to a benzaldehyde followed by oxidation. For compound 37, a potential precursor of the anthraquinone part of mumbaistatin, various approaches via aryne/phthalide annulations were developed and evaluated. The required functionalized arenes were prepared exploiting, among others, regioselective bromination and ortho-lithiation reactions. Coupling reactions of the anthracene-carbaldehyde 44 derived from 37 with various metalated arenes proved to be unexpectedly difficult and failed so far. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00427-7
• 作为产物：
  描述：

  4-[1',3']dioxan-2'-yl-6-methoxymethoxy-5-methoxymethyl-3-oxo-1,3-dihydroisobenzo-furan-1-carbonitrile 在 2,2,6,6-四甲基哌啶 、 sodium dithionate 、 氢氧化钾 、 正丁基锂 、 四丁基溴化铵 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 18.0h， 生成 2'-(9,10-dimethoxy-3,8-bismethoxymethoxy-2-methoxymethylanthracen-1-yl)-[1',3']-dioxane
  参考文献：
  名称：

  Studies towards the total synthesis of mumbaistatin: synthesis of highly substituted benzophenone and anthraquinone building blocks

  摘要：

  Model compounds and building blocks for a planned total synthesis of the highly potent glucose-6-phosphate (G6P) translocase inhibitor mumbaistatin (1) and structural analogs were elaborated: compound 1 represents a lead structure in the development of potential new antidiabetic drugs. With the model substrate 20 it was demonstrated that highly functionalized, tetra-ortho-substituted benzophenones can be prepared by nucleophilic addition of an aryllithium-building block to a benzaldehyde followed by oxidation. For compound 37, a potential precursor of the anthraquinone part of mumbaistatin, various approaches via aryne/phthalide annulations were developed and evaluated. The required functionalized arenes were prepared exploiting, among others, regioselective bromination and ortho-lithiation reactions. Coupling reactions of the anthracene-carbaldehyde 44 derived from 37 with various metalated arenes proved to be unexpectedly difficult and failed so far. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00427-7