4-(((methoxycarbonyl)oxy)methyl)benzaldehyde | 951406-29-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(((methoxycarbonyl)oxy)methyl)benzaldehyde
• 英文别名: (4-Formylphenyl)methyl methyl carbonate
• CAS: 951406-29-4
• 化学式: C₁₀H₁₀O₄
• 分子量: 194.187
• InChiKey: AVFVBLOOQHTZFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(((methoxycarbonyl)oxy)methyl)benzaldehyde 在 氯化亚砜 、 三乙胺 作用下， 以 氯仿 、 苯 为溶剂， 反应 16.5h， 生成
  参考文献：
  名称：

  Optimization of the Indenone Ring of Indenoisoquinoline Topoisomerase I Inhibitors

  摘要：

  Two series of indenoisoquinoline topoisomerase I inhibitors have been prepared to investigate optimal substituents on the indenone ring at the 9-position. The more exhaustive series was prepared using a nitrated isoquinoline ring that has been previously demonstrated to enhance biological activity. After preliminary biological evaluation, a more focused series of inhibitors was prepared utilizing a 2,3-dimethoxy-substituted isoquinoline ring. The results of the two series indicate the existence of superior functional groups such as methoxy, fluorine, and cyano for the indenoisoquinoline 9-position. Interestingly, these functional groups coincide with established structure-activity relationships for the 11-position of camptothecin.

  DOI：

  10.1021/jm070307+
• 作为产物：
  描述：

  氯甲酸甲酯 、 对羟基甲基苯甲醛 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以66%的产率得到4-(((methoxycarbonyl)oxy)methyl)benzaldehyde
  参考文献：
  名称：

  Optimization of the Indenone Ring of Indenoisoquinoline Topoisomerase I Inhibitors

  摘要：

  Two series of indenoisoquinoline topoisomerase I inhibitors have been prepared to investigate optimal substituents on the indenone ring at the 9-position. The more exhaustive series was prepared using a nitrated isoquinoline ring that has been previously demonstrated to enhance biological activity. After preliminary biological evaluation, a more focused series of inhibitors was prepared utilizing a 2,3-dimethoxy-substituted isoquinoline ring. The results of the two series indicate the existence of superior functional groups such as methoxy, fluorine, and cyano for the indenoisoquinoline 9-position. Interestingly, these functional groups coincide with established structure-activity relationships for the 11-position of camptothecin.

  DOI：

  10.1021/jm070307+

文献信息

• NHC-Catalyzed ε-Umpolung via <i>p</i>-Quinodimethanes and Its Nucleophilic Addition to Ketones
  作者：Lei Dai、Song Ye

  DOI：10.1021/acscatal.9b04409

  日期：2020.1.17

  An unprecedented NHC-catalyzed generation of p-quinodimethanes via ε-umpolung of 4-(chloromethyl)benzaldehydes and the following ε-addition to active ketones was developed. A series of active ketones, such as trifluoromethyl ketones and 1,2-dicarbonyl compounds, worked well for the reaction, giving the corresponding trifluoromethyl alcohols and α-hydroxyl carbonyl compounds in good yields.

  开发了一种空前的NHC催化产物，它是通过4-（氯甲基）苯甲醛的ε-苯甲酸酯和随后的ε-添加到活性酮中而生成的对-喹二甲烷。一系列活性酮，例如三氟甲基酮和1,2-二羰基化合物，对反应反应良好，从而以高收率得到相应的三氟甲基醇和α-羟基羰基化合物。