2,2-dibutyl-2H-1-benzopyran

• 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: 2,2-dibutyl-2H-1-benzopyran
• 英文别名: 2,2-dibutyl-2H-chromene；2,2-Dibutyl-2H-chromen；2,2-dibutylchromene
• 化学式: C₁₇H₂₄O
• 分子量: 244.377
• InChiKey: PPIPDMPEHMAPOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.21
• 重原子数：
  18.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  3-溴-2H-苯并吡喃-2-酮 以 甲苯 为溶剂， 反应 0.5h， 生成 2,2-dibutyl-2H-1-benzopyran
  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

• Maitte, Annales de Chimie (Cachan, France), 1954, vol. <12> 9, p. 431,363
  作者：Maitte

  DOI：——

  日期：——
• The Chemistry of Vitamin E. XXII. The Reaction between Grignard Reagents and Coumarins and Hydrocoumarins¹
  作者：Lee Irvin Smith、P. M. Ruoff

  DOI：10.1021/ja01858a040

  日期：1940.1
• THE ACTION OF ALKYLMAGNESIUM HALIDES ON COUMARIN AND RELATED COMPOUNDS. SYNTHESIS OF 2,2-DIALKYL-1,2-BENZOPYRANS
  作者：R. L. SHRINER、A. G. SHARP

  DOI：10.1021/jo01217a007

  日期：1939.11
• 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.