methyl 2-butyl-7,7-dimethyl-5-oxo-3,4,5,6,7,8-hexahydro-2H-chromene-3-carboxylate | 1075686-36-0

• 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: methyl 2-butyl-7,7-dimethyl-5-oxo-3,4,5,6,7,8-hexahydro-2H-chromene-3-carboxylate
• 英文别名: (2R,3S)-methyl 2-butyl-7,7-dimethyl-5-oxo-3,4,5,6,7,8-hexahydro-2H-chromene-3-carboxylate；methyl (2R,3S)-2-butyl-7,7-dimethyl-5-oxo-3,4,6,8-tetrahydro-2H-chromene-3-carboxylate
• CAS: 1075686-36-0
• 化学式: C₁₇H₂₆O₄
• 分子量: 294.391
• InChiKey: VTYBFPBOYORAJU-GXTWGEPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 、 Methyl 3-acetyloxy-2-methylideneheptanoate 在 三乙胺 作用下， 反应 4.5h， 以21%的产率得到methyl 2-butyl-7,7-dimethyl-5-oxo-3,4,5,6,7,8-hexahydro-2H-chromene-3-carboxylate
  参考文献：
  名称：

  An efficient synthesis of 3-arylmethyl-7,8-dihydro-6H-chromene-2,5-diones from Baylis–Hillman adduct acetates under solvent-free conditions

  摘要：

  A simple, efficient synthesis of 3-arylmethyl-7,8-dihydro-6H-chromene-2,5-dione 4 from Baylis-Hillman adduct acetates derived from aromatic aldehydes and cyclohexane-1,3-diones under solvent-free conditions is described. Interestingly, when Baylis-Hillman adducts derived from aliphatic aldehydes were tested under the similar conditions, the unexpected stereoisomers 5 and 6 were obtained in moderate yields. A plausible mechanism for the formation of 4-6 is proposed. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.04.003