2,3,7-trimethylchromone | 106949-32-0

• 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: 2,3,7-trimethylchromone
• 英文别名: 2,3,7-trimethyl-chromen-4-one；2,3,7-Trimethyl-chromen-4-on；2,3,7-Trimethyl-4H-1-benzopyran-4-one；2,3,7-trimethylchromen-4-one
• CAS: 106949-32-0
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: ZUFWUUODOHMEON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  2,3,7-trimethylchromone 在 potassium tert-butylate 作用下， 以 苯 为溶剂， 反应 14.0h， 生成 cis-1,2,2a,8a-tetrahydro-2a,5,8a-trimethyl-8-methylenebenzocyclobutapyran
  参考文献：
  名称：

  Rapid, high-yield synthesis of the marine sesquiterpenes debromoaplysin and aplysin via the acid-catalyzed rearrangement of a cyclobutachromanol

  摘要：

  A short, stereocontrolled, high-yield synthesis of debromoaplysin (1) and aplysin (2) from the chromone 13 is described. The cycloaddition of ethylene to 13, followed by the addition of methylmagnesium iodide to the cycloadduct, furnished the cyclobutachromanol 15. Treatment of 15 in benzene with BF3.Et2O furnished a mixture of the alkenes 16 and 17, which can be visualized as arising by way of the initial 1,2-migration of the external and internal bonds, respectively, of the cyclobutane ring of 15. Similar rearrangement of 18, an ethyl analogue of 15, yielded 19 and 20. Rearrangement of 15 on treatment with sulfuric acid in petroleum ether at -78-degrees-C furnished, almost exclusively, 17. In contrast, when performed in nitroethane at -78-degrees-C, the same reaction afforded 16 exclusively. Thus, the solvent exerted a remarkable effect on the outcome of the rearrangement. Since alkene 16 had previously been converted to 1 and 2, this work represents an improved synthesis of the two sesquiterpenes.

  DOI：

  10.1021/jo00031a026
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氢碘酸 作用下， 生成 2,3,7-trimethylchromone
  参考文献：
  名称：

  116. 3-烷基色酮的制备。取代对色酮中2-甲基反应性的影响

  摘要：

  DOI：

  10.1039/jr9430000434

文献信息

• Sabui, Subir Kumar; Mondal, Pranab; Venkateswaran, Ramanathapuram V., Journal of Chemical Research - Part S, 2002, # 9, p. 428 - 429
  作者：Sabui, Subir Kumar、Mondal, Pranab、Venkateswaran, Ramanathapuram V.

  DOI：——

  日期：——
• 222. Lichen acids. Part III. The constitution of barbatic acid and the syntheses of isorhizonic acid and methyl barbatate
  作者：Alexander Robertson、Richard John Stephenson

  DOI：10.1039/jr9320001675

  日期：——
• 116. Preparation of 3-alkylchromones. Effect of substitution on the reactivity of the 2-methyl group in chromones
  作者：Ahmad Zaki、Raymond C. Azzam

  DOI：10.1039/jr9430000434

  日期：——
• Rapid, high-yield synthesis of the marine sesquiterpenes debromoaplysin and aplysin via the acid-catalyzed rearrangement of a cyclobutachromanol
  作者：Asok Nath、Arun Ghosh、Ramanathapuram V. Venkateswaran

  DOI：10.1021/jo00031a026

  日期：1992.2

  A short, stereocontrolled, high-yield synthesis of debromoaplysin (1) and aplysin (2) from the chromone 13 is described. The cycloaddition of ethylene to 13, followed by the addition of methylmagnesium iodide to the cycloadduct, furnished the cyclobutachromanol 15. Treatment of 15 in benzene with BF3.Et2O furnished a mixture of the alkenes 16 and 17, which can be visualized as arising by way of the initial 1,2-migration of the external and internal bonds, respectively, of the cyclobutane ring of 15. Similar rearrangement of 18, an ethyl analogue of 15, yielded 19 and 20. Rearrangement of 15 on treatment with sulfuric acid in petroleum ether at -78-degrees-C furnished, almost exclusively, 17. In contrast, when performed in nitroethane at -78-degrees-C, the same reaction afforded 16 exclusively. Thus, the solvent exerted a remarkable effect on the outcome of the rearrangement. Since alkene 16 had previously been converted to 1 and 2, this work represents an improved synthesis of the two sesquiterpenes.