3-cyano-7-methoxymethoxy-1(3H)isobenzo-furanone | 113232-79-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 3-cyano-7-methoxymethoxy-1(3H)isobenzo-furanone
• 英文别名: 4-(methoxymethoxy)-3-oxo-1H-2-benzofuran-1-carbonitrile
• CAS: 113232-79-4
• 化学式: C₁₁H₉NO₄
• 分子量: 219.197
• InChiKey: GHTOHXPDBZJKSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  68.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-cyano-7-methoxymethoxy-1(3H)isobenzo-furanone 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
• 作为产物：
  描述：

  2-formyl-6-methoxymethoxy-N,N-diethylbenzamide 在 potassium cyanide 、 18-冠醚-6 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 10.25h， 生成 3-cyano-7-methoxymethoxy-1(3H)isobenzo-furanone
  参考文献：
  名称：

  Okazaki, Kousuke; Nomura, Keiichi; Yoshii, Eiichi, Synthetic Communications, 1987, vol. 17, # 9, p. 1021 - 1028

  摘要：

  DOI：

文献信息

• Carbene-Catalyzed Formal [5 + 5] Reaction for Coumarin Construction and Total Synthesis of Defucogilvocarcins
  作者：Xuan Huang、Tingshun Zhu、Zhijian Huang、Yuexia Zhang、Zhichao Jin、Giuseppe Zanoni、Yonggui Robin Chi

  DOI：10.1021/acs.orglett.7b03102

  日期：2017.11.17

  An N-heterocyclic carbene-catalyzed formal [5 + 5] reaction between enals and furanones that generates multisubstituted coumarins in a single step is reported. Five atoms in each of the substrates are involved in this catalytic process to form a benzene and a lactone ring. The power of the method is further demonstrated in metal-free total syntheses of several natural products (defucogilvocarcins M

  据报道，在烯醛和呋喃酮之间的N杂环卡宾催化的正式[5 + 5]反应可在一个步骤中生成多取代的香豆素。每个底物中的五个原子参与该催化过程以形成苯和内酯环。该方法的功效在以香豆素为关键结构基序的几种天然产物（去甲福尔霉素M，E和V）的无金属全合成中得到了进一步证明。
• OKAZAKI, KOUSUKE;NOMURA, KEIICHI;YOSHII, EIICHI, SYNTH. COMMUN., 17,(1987) N 9, 1021-1027
  作者：OKAZAKI, KOUSUKE、NOMURA, KEIICHI、YOSHII, EIICHI

  DOI：——

  日期：——
• 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.
• Okazaki, Kousuke; Nomura, Keiichi; Yoshii, Eiichi, Synthetic Communications, 1987, vol. 17, # 9, p. 1021 - 1028
  作者：Okazaki, Kousuke、Nomura, Keiichi、Yoshii, Eiichi

  DOI：——

  日期：——