1-methyl 4-(2-formylphenyl)-(Z)-but-2-en-1,4-dioate | 925230-63-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 1-methyl 4-(2-formylphenyl)-(Z)-but-2-en-1,4-dioate
• 英文别名: 2-formylphenyl methyl maleate；4-O-(2-formylphenyl) 1-O-methyl (Z)-but-2-enedioate
• CAS: 925230-63-3
• 化学式: C₁₂H₁₀O₅
• 分子量: 234.208
• InChiKey: OKVPVFLTHQSJNH-SREVYHEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-methyl 4-(2-formylphenyl)-(Z)-but-2-en-1,4-dioate 反应 0.25h， 以99%的产率得到2-formylphenyl methyl fumarate
  参考文献：
  名称：

  Microwave-assisted solvent-free intramolecular 1,3-dipolar cycloaddition reactions leading to hexahydrochromeno[4,3-b]pyrroles: scope and limitations

  摘要：

  We report the microwave-assisted solvent-free synthesis of hexahydrochromeno[4,3-b]pyrroles. Intramolecular 1,3-dipolar cycloadditions proceed under these conditions within 15-40 min in 16-84% yields. An influence of the microwave irradiation upon various [3+2] cycloaddition reaction intermediates was studied. Additionally, a scope and limitations of these reactions including an influence of the dipolarophile geometry upon the cycloaddition selectivity and steric demands of the dipole upon its reactivity were also disclosed. These observations led us to postulate a preferable transition state of the reaction. Finally, an influence of the microwave irradiation to the isomerization of activated olefins was also described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.10.074
• 作为产物：
  描述：

  顺丁烯二酸单甲酯 在 氯化亚砜 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.17h， 生成 1-methyl 4-(2-formylphenyl)-(Z)-but-2-en-1,4-dioate
  参考文献：
  名称：

  分子内无碱催化维蒂希反应：苯并恶庚啶酮的合成

  摘要：

  通过无碱膦催化的Wittig反应开发了一种简单的两步合成苯并庚二酮的方法。使用3-甲基-1-苯基-2-膦-1-氧化物作为前催化剂，使用三甲氧基硅烷作为还原剂。另外，苯甲酸被用作催化剂以促进氧化膦的还原。机理研究表明，香豆素是副产物的形成，这是通过2D NMR实验确定的。报道了对所制备的苯并庚二酮的代谢活性测试的初步结果。

  DOI：

  10.1021/acs.joc.8b02789

文献信息

• Microwave-assisted solvent-free intramolecular 1,3-dipolar cycloaddition reactions leading to hexahydrochromeno[4,3-b]pyrroles: scope and limitations
  作者：Jiří Pospíšil、Milan Potáček

  DOI：10.1016/j.tet.2006.10.074

  日期：2007.1

  We report the microwave-assisted solvent-free synthesis of hexahydrochromeno[4,3-b]pyrroles. Intramolecular 1,3-dipolar cycloadditions proceed under these conditions within 15-40 min in 16-84% yields. An influence of the microwave irradiation upon various [3+2] cycloaddition reaction intermediates was studied. Additionally, a scope and limitations of these reactions including an influence of the dipolarophile geometry upon the cycloaddition selectivity and steric demands of the dipole upon its reactivity were also disclosed. These observations led us to postulate a preferable transition state of the reaction. Finally, an influence of the microwave irradiation to the isomerization of activated olefins was also described. (c) 2006 Elsevier Ltd. All rights reserved.
• Intramolecular Base-Free Catalytic Wittig Reaction: Synthesis of Benzoxepinones
  作者：Aiga Grandane、Lars Longwitz、Catrin Roolf、Anke Spannenberg、Hugo Murua Escobar、Christian Junghanss、Edgars Suna、Thomas Werner

  DOI：10.1021/acs.joc.8b02789

  日期：2019.2.1

  A straightforward two-step synthesis of benzoxepinones was developed via base-free phosphane-catalyzed Wittig reaction. 3-Methyl-1-phenyl-2-phospholene 1-oxide was used as a precatalyst and trimethoxysilane as a reducing agent. Additionally benzoic acid is employed as a catalyst to facilitate the reduction of the phosphane oxide. Mechanistic investigation revealed the formation of a coumarin as a side

  通过无碱膦催化的Wittig反应开发了一种简单的两步合成苯并庚二酮的方法。使用3-甲基-1-苯基-2-膦-1-氧化物作为前催化剂，使用三甲氧基硅烷作为还原剂。另外，苯甲酸被用作催化剂以促进氧化膦的还原。机理研究表明，香豆素是副产物的形成，这是通过2D NMR实验确定的。报道了对所制备的苯并庚二酮的代谢活性测试的初步结果。