1-[1',3']dioxan-2'-yl-3,8-bismethoxymethoxy-2-methoxymethylanthraquinone | 565176-59-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-[1',3']dioxan-2'-yl-3,8-bismethoxymethoxy-2-methoxymethylanthraquinone
• 英文别名: 1-(1,3-Dioxan-2-yl)-3,8-bis(methoxymethoxy)-2-(methoxymethyl)anthracene-9,10-dione；1-(1,3-dioxan-2-yl)-3,8-bis(methoxymethoxy)-2-(methoxymethyl)anthracene-9,10-dione
• CAS: 565176-59-2
• 化学式: C₂₄H₂₆O₉
• 分子量: 458.465
• InChiKey: QYNTUQGZOPLUTR-UHFFFAOYSA-N

物化性质

• 沸点：
  638.3±55.0 °C(Predicted)
• 密度：
  1.290±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  98.8
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-[1',3']dioxan-2'-yl-3,8-bismethoxymethoxy-2-methoxymethylanthraquinone 在 sodium dithionate 、 氢氧化钾 、 硫酸 、 四丁基溴化铵 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 90.0h， 生成 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：

  2-(3-hydroxyphenyl)-1,3-dioxane 在 18-冠醚-6 2,2,6,6-四甲基哌啶 、 potassium cyanide 、 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 四甲基乙二胺 、 叔丁基锂 、 仲丁基锂 、 sodium acetate 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 环己烷 、 N,N-二甲基甲酰胺 、 正戊烷 、 苯 为溶剂， 反应 17.58h， 生成 1-[1',3']dioxan-2'-yl-3,8-bismethoxymethoxy-2-methoxymethylanthraquinone
  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

文献信息

• Studies towards the total synthesis of mumbaistatin: synthesis of highly substituted benzophenone and anthraquinone building blocks
  作者：Florian Kaiser、Lothar Schwink、Janna Velder、Hans-Günther Schmalz

  DOI：10.1016/s0040-4020(03)00427-7

  日期：2003.4

  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.