3-(3,5-dichloro-2,6-dimethoxy-4-methylphenyl)-5,7-dimethoxy-4-(3-methylbut-2-enyl)isobenzofuran-1(3H)-one | 1258391-62-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-(3,5-dichloro-2,6-dimethoxy-4-methylphenyl)-5,7-dimethoxy-4-(3-methylbut-2-enyl)isobenzofuran-1(3H)-one
• CAS: 1258391-62-6
• 化学式: C₂₄H₂₆Cl₂O₆
• 分子量: 481.373
• InChiKey: FZJFEIMBCNAJSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  (2-formyl-3,5-dimethoxy-6-(3-methylbut-2-enyl)phenyl)(3,5-dichloro-2,6-dimethoxy-4-methylphenyl)methanone 在 硫代乙氧基锂 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以13%的产率得到3-(3,5-dichloro-2,6-dimethoxy-4-methylphenyl)-5,7-dimethoxy-4-(3-methylbut-2-enyl)isobenzofuran-1(3H)-one
  参考文献：
  名称：

  Nucleophile- or Light-Induced Synthesis of 3-Substituted Phthalides from 2-Formylarylketones

  摘要：

  The surprisingly facile conversion (isomerization) of 2-formyl-arylketones into 3-substituted phthalides, as observed for the marine natural product pestalone and its per-O-methylated derivative, was investigated using a series of simple 2-acylbenzaldehydes as substrates. The transformation generally proceeds smoothly in DMSO, either in a Cannlzarro-Tishchenko-type reaction under nucleophile catalysis (NaCN) or under photochemical conditions (DMSO, 350 nm).

  DOI：

  10.1021/ol300757m

文献信息

• Total Synthesis of the Marine Antibiotic Pestalone and its Surprisingly Facile Conversion into Pestalalactone and Pestalachloride A
  作者：Nikolay Slavov、Ján Cvengroš、Jörg-Martin Neudörfl、Hans-Günther Schmalz

  DOI：10.1002/anie.201003755

  日期：——

  Surprise, surprise! The total synthesis of the marine natural product pestalone (1), a highly substituted benzophenone with strong antibiotic acitivity, has provided insight into the surprising tendency of this and related molecules to undergo intramolecular Cannizzaro–Tishchenko‐type reactions. Pestalone can be readily converted into pestalachloride A, a strongly antifungal metabolite isolated from

  惊喜，惊喜！海洋天然害虫单独（1）（具有强抗生素活性的高度取代的二苯甲酮）的总合成提供了对该分子及相关分子进行分子内Cannizzaro–Tishchenko型反应的惊人趋势的深入了解。通过用pH为8的氨进行简单处理，即可轻松将Pestalone转化为瘟疫杀菌素A，这是一种从内生真菌中分离出来的强抗真菌代谢产物。