3-chloro-3,4-dihydro-2,4-diphenyl-2H-1-benzopyran-2-ol | 133379-92-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 3-chloro-3,4-dihydro-2,4-diphenyl-2H-1-benzopyran-2-ol
• 英文别名: 3-chloro-2,4-diphenyl-3,4-dihydrochromen-2-ol
• CAS: 133379-92-7
• 化学式: C₂₁H₁₇ClO₂
• 分子量: 336.818
• InChiKey: XCSXUQABSMYGKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.66
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  3-氯香豆素 、 phenylmagnesium bromide 、 水 以20%的产率得到
  参考文献：
  名称：

  ALBEROLA, ANGEL;CALVO, BLANCA;ORTEGA, ALFONSO GONZALEZ;VICENTE, MARTINA;G+, J. CHEM. SOC. PERKIN TRANS. PT 1,(1991) N, C. 203-210

  摘要：

  DOI：

文献信息

• Reaction of 3-halogeno-2H-1-benzopyran-2-ones with organometallic compounds. Synthesis of 4-Alkyl-2H-1-benzopyran-2-ones. X-Ray molecular structure of 3-bromo-3,4-dihydro-4-isopropylcoumarin
  作者：Angel Alberola、Blanca Calvo、Alfonso Gonzalez Ortega、Martina Vicente、Santiago G. Granda、Juan F. Van der Maelen

  DOI：10.1039/p19910000203

  日期：——

  3-Halogeno-2H-1-benzopyran-2-ones react with magnesium, lithium, aluminium and copper derivatives to give 3,4-dihydrocoumarins and 3-(o-hydroxyphenyl)propenols as major products. The nature and the ratio of the products in the final mixture depend on the solvent and on the organometallic reagent. Grignard derivatives yield 1,4-monoalkylation compounds in tetrahydrofuran (THF) or 1,2-dialkylation derivatives in toluene. In some cases the dehalogenation competes with the 1,2-alkylation process in the reactions with alkyllithiums. The presence of the halogen at C-3 increases the reductive ability of organoaluminiums. In general, the reaction with lithium dialkylcuprates leads to complex mixtures of products. The 4-alkyl-3-halogeno-3,4-dihydrocoumarins obtained undergo dehydrohalogenation easily, and lead to 4-alkylcoumarins in good yields. The tandem alkylation-dehydrohalogenation of 3-halogeno-2H-1-benzopyran-2-ones constitutes a versatile synthesis of 4-alkylcoumarins.
• ALBEROLA, ANGEL;CALVO, BLANCA;ORTEGA, ALFONSO GONZALEZ;VICENTE, MARTINA;G+, J. CHEM. SOC. PERKIN TRANS. PT 1,(1991) N, C. 203-210
  作者：ALBEROLA, ANGEL、CALVO, BLANCA、ORTEGA, ALFONSO GONZALEZ、VICENTE, MARTINA、G+

  DOI：——

  日期：——