3-chloro-2H-1-benzopyran-2-ol | 133380-02-6

• 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-chloro-2H-1-benzopyran-2-ol
• 英文别名: 3-chloro-2H-chromen-2-ol
• CAS: 133380-02-6
• 化学式: C₉H₇ClO₂
• 分子量: 182.606
• InChiKey: BLJXQMQKZROBAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.98
• 重原子数：
  12.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 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 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 30.0h， 以7%的产率得到(E)-2-chloro-3-(o-hydroxyphenyl)prop-2-en-1-ol
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1039/p19910000203

文献信息

• 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：——
• 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.