(Z)-Benzyliden-4,7-dimethylbenzofuran-3(2H)-on | 38216-68-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 橙酮类黄酮
• 英文名称: (Z)-Benzyliden-4,7-dimethylbenzofuran-3(2H)-on
• 英文别名: (Z)-4,6-dimethylbenzylidenecoumaranone；2-benzylidene-4,6-dimethyl-benzofuran-3-one；2-Benzyliden-4,6-dimethyl-benzofuran-3-on；(2Z)-2-benzylidene-4,6-dimethyl-1-benzofuran-3(2H)-one；(2Z)-2-benzylidene-4,6-dimethyl-1-benzofuran-3-one
• CAS: 38216-68-1
• 化学式: C₁₇H₁₄O₂
• 分子量: 250.297
• InChiKey: PIWCODVTFCWFAG-GDNBJRDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  benzylpentacarbonylmanganese 、 (Z)-Benzyliden-4,7-dimethylbenzofuran-3(2H)-on 以 petroleum ether 为溶剂， 以58%的产率得到[[4,6-dimethylbenzo[d]furan-3(5H)-on-κO-2-ylidene]phenylmethyl]tetracarbonylmanganese
  参考文献：
  名称：

  Preparation of cyclomanganated chalcones and their reactions with methyl acrylate and other α, β-unsaturated carbonyl compounds

  摘要：

  Chalcones [(E)-1,3-diarylprop-2-en-1-ones] react with benzyltetracarbonylmanganese under reflux in petroleum spirit to give two types of cyclomanganation products. The first, involving metallation at the alkenyl beta-carbon of the enone, are derivatives of [[1-phenyl-2-phenylcarbonyl-kappa O]ethenyl-kappa C-1]tetracarbonylmanganese, while the second type, manganated at the aryl ring ortho-carbon, are derivatives of [2-[3-phenylprop-2-en-1-onyl-kappa O]phenyl-kappa C-1]tetracarbonylmangane In general, more ''alkene-manganated'' than ''ring-manganated'' product is formed, with the ratio influenced significantly by certain substituents, e.g. a 4-CF3 substituent on the phenyl ring at C3 of the enone strongly promotes ''alkene-manganation''. in some cases there are minor by-products derived from coupling of two chalcone molecules after initial cyclomanganation. The crystal structures are reported for two such products, [2-((1S*,2R*,3S*)-1-hydroxy-1-((E)-2-(2-trifluoromethylphenyl)ethenyl)-3-(2-trifluoromethylphenyl)-6-methoxy-2-indanylcarbonyl- kappa O)-6-methoxyphenyl-kappa C-1]tetracarbonylmanganese and (1S*,4S*,5R*)-5-(4-bromobenzoyl)-1-(4-bromophenyl)-3,4-di-(4-trifluoromethylphenyl)cyclopent-2-en-1-ol.In acetonitrile under reflux, alkene-manganated chalcones react with methyl acrylate (methyl propenoate) to form derivatives of methyl (E)-4,6-diphenyl-6-oxohex-2-enoate and of 5-(2-methoxycarbonylethyl)-3,5-diphenylfuran-2-(5H)-one. The latter butenolides are not formed when the reactions are carried out in carbon tetrachloride, only the former alpha,beta-unsaturated esters. By contrast, in a few reactions studied, acrolein (propenal) and methyl vinyl ketone (but-3-en-2-one) give only the butenolide products when treated with alkene-manganated chalcones in refluxing acetonitrile. An exception is the reaction of methyl vinyl ketone with [[1 -(3,4,5-trimethoxyphenyl)-2-(4-chlorophenylcarbonyl-kappa O)]ethenyl-kappa C-1]tetracarbonylmanganese to form the cyclized product 5-acetyl-1-(4-chlorophenyl)3-(3,4,5-trimethoxyphenyl)cyclopent-2-en-1-ol.

  DOI：

  10.1016/0022-328x(95)05488-b
• 作为产物：
  描述：

  苯甲醛 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydroxide 作用下， 生成 (Z)-Benzyliden-4,7-dimethylbenzofuran-3(2H)-on
  参考文献：
  名称：

  v. Auwers, Chemische Berichte, 1916, vol. 49, p. 825

  摘要：

  DOI：

表征谱图