(E)-2-bromo-1-(o-hydroxyphenyl)hept-1-en-3-ol | 133380-28-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (E)-2-bromo-1-(o-hydroxyphenyl)hept-1-en-3-ol
• 英文别名: 2-[(E)-2-bromo-3-hydroxyhept-1-enyl]phenol
• CAS: 133380-28-6
• 化学式: C₁₃H₁₇BrO₂
• 分子量: 285.181
• InChiKey: QFHLNKDFQJTTBS-PKNBQFBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.68
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (E)-2-bromo-1-(o-hydroxyphenyl)hept-1-en-3-ol 在 silica gel 作用下， 以 xylene 为溶剂， 反应 3.0h， 以42%的产率得到3-bromo-2-butyl-2H-chromene
  参考文献：
  名称：

  Alberola, Angel; Calvo, Blanca; Gonzalez-Ortega, Alfonso, Heterocycles, 1994, vol. 38, # 4, p. 819 - 832

  摘要：

  DOI：
• 作为产物：
  描述：

  3-溴-2H-苯并吡喃-2-酮 、 三异丁基铝 以 甲苯 为溶剂， 反应 10.0h， 以15%的产率得到(E)-2-bromo-1-(o-hydroxyphenyl)hept-1-en-3-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; Gonzalez-Ortega, Alfonso, Heterocycles, 1994, vol. 38, # 4, p. 819 - 832
  作者：Alberola, Angel、Calvo, Blanca、Gonzalez-Ortega, Alfonso、Lopez, Cristina、Villafane, Fernando

  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.