3,4-dihydro-2-methoxy-5,6-dimethyl-2H-pyran | 176376-24-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-dihydro-2-methoxy-5,6-dimethyl-2H-pyran
• 英文别名: 2-methoxy-5,6-dimethyl-3,4-dihydro-2H-pyran
• CAS: 176376-24-2
• 化学式: C₈H₁₄O₂
• 分子量: 142.198
• InChiKey: FXURVMARHRMNOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  异氰酸苯磺酰酯 、 3,4-dihydro-2-methoxy-5,6-dimethyl-2H-pyran 以 氘代氯仿 为溶剂， 以65%的产率得到(3S,6R)-3-acetyl-1-(benzenesulfonyl)-6-methoxy-3-methylpiperidin-2-one
  参考文献：
  名称：

  Addition−Rearrangement of Aryl- and Alkoxysulfonyl Isocyanates with 5-Methyl-Substituted 3,4-Dihydro-2-methoxy-2H-pyrans. Selective Synthesis of Functionalized 2-Piperidones¹

  摘要：

  3,4-Dihydro-2-methoxy-5-methyl-2H-pyran and 3,4-dihydro-2-methoxy-5,6-dimethyl-2H-pyran undergo addition-rearrangement reactions with arylsulfonyl isocyanates to generate the corresponding 3-formyl- and 3-acetyl-6-methoxy-3-methyl-1-(arylsulfonyl)-2-piperidones. For example, 3,4-dihydro-2-methoxy-5-methyl-2H-pyran and phenylsulfonyl isocyanate afforded 3-formyl-6-methoxy-3-methyl-1-(phenylsulfonyl)-2-piperidone as a separable trans/cis mixture in high yield. The more reactive phenoxysulfonyl and alkoxysulfonyl isocyanates provided analogous results.

  DOI：

  10.1021/jo951868o
• 作为产物：
  描述：

  2-甲基-1-丁烯-3-酮 、 乙烯基甲醚 在 对苯二酚 、 zinc(II) chloride 作用下， 以57%的产率得到3,4-dihydro-2-methoxy-5,6-dimethyl-2H-pyran
  参考文献：
  名称：

  Addition−Rearrangement of Aryl- and Alkoxysulfonyl Isocyanates with 5-Methyl-Substituted 3,4-Dihydro-2-methoxy-2H-pyrans. Selective Synthesis of Functionalized 2-Piperidones¹

  摘要：

  3,4-Dihydro-2-methoxy-5-methyl-2H-pyran and 3,4-dihydro-2-methoxy-5,6-dimethyl-2H-pyran undergo addition-rearrangement reactions with arylsulfonyl isocyanates to generate the corresponding 3-formyl- and 3-acetyl-6-methoxy-3-methyl-1-(arylsulfonyl)-2-piperidones. For example, 3,4-dihydro-2-methoxy-5-methyl-2H-pyran and phenylsulfonyl isocyanate afforded 3-formyl-6-methoxy-3-methyl-1-(phenylsulfonyl)-2-piperidone as a separable trans/cis mixture in high yield. The more reactive phenoxysulfonyl and alkoxysulfonyl isocyanates provided analogous results.

  DOI：

  10.1021/jo951868o

文献信息

• Addition−Rearrangement of Aryl- and Alkoxysulfonyl Isocyanates with 5-Methyl-Substituted 3,4-Dihydro-2-methoxy-<i>2H</i>-pyrans. Selective Synthesis of Functionalized 2-Piperidones¹
  作者：Edwin Jao、Paul B. Slifer、Roger Lalancette、Stan S. Hall

  DOI：10.1021/jo951868o

  日期：1996.1.1

  3,4-Dihydro-2-methoxy-5-methyl-2H-pyran and 3,4-dihydro-2-methoxy-5,6-dimethyl-2H-pyran undergo addition-rearrangement reactions with arylsulfonyl isocyanates to generate the corresponding 3-formyl- and 3-acetyl-6-methoxy-3-methyl-1-(arylsulfonyl)-2-piperidones. For example, 3,4-dihydro-2-methoxy-5-methyl-2H-pyran and phenylsulfonyl isocyanate afforded 3-formyl-6-methoxy-3-methyl-1-(phenylsulfonyl)-2-piperidone as a separable trans/cis mixture in high yield. The more reactive phenoxysulfonyl and alkoxysulfonyl isocyanates provided analogous results.