6-(4-Chloro-phenyl)-4-methyl-5,6-dihydro-pyran-2-one | 286372-79-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 6-(4-Chloro-phenyl)-4-methyl-5,6-dihydro-pyran-2-one
• 英文别名: 2-(4-Chlorophenyl)-4-methyl-2,3-dihydropyran-6-one
• CAS: 286372-79-0
• 化学式: C₁₂H₁₁ClO₂
• 分子量: 222.671
• InChiKey: CPKCIDHCUMVLFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  1
• 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：

  6-(4-Chloro-phenyl)-4-methyl-5,6-dihydro-pyran-2-one 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以59%的产率得到2-cis-4-trans-3-Methyl-5-(4-chlor-phenyl)-pentadien-2,4-saeure
  参考文献：
  名称：

  A general synthesis of (2Z)-terpenoic acids

  摘要：

  A three-step synthesis of (2Z), (4E)-polyenic acids 6 is described. Condensation of aldehydes 1 with potassium prenal enolate led to dihydropyranols 3 which were oxidized into dihydropyrones 5, precursors of (2Z), (4E)-polyenic acids 6. The procedure was applied to a synthesis of 13-cis-retinoic acids from beta-ionylidene acetaldehydes. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00457-3
• 作为产物：
  描述：

  6-(4-chlorophenyl)-4-methyl-5,6-dihydro-2H-pyran-2-ol 在 chromium(VI) oxide 、 硫酸 作用下， 以 水 、 丙酮 为溶剂， 以94%的产率得到6-(4-Chloro-phenyl)-4-methyl-5,6-dihydro-pyran-2-one
  参考文献：
  名称：

  A general synthesis of (2Z)-terpenoic acids

  摘要：

  A three-step synthesis of (2Z), (4E)-polyenic acids 6 is described. Condensation of aldehydes 1 with potassium prenal enolate led to dihydropyranols 3 which were oxidized into dihydropyrones 5, precursors of (2Z), (4E)-polyenic acids 6. The procedure was applied to a synthesis of 13-cis-retinoic acids from beta-ionylidene acetaldehydes. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00457-3

文献信息

• A general synthesis of (2Z)-terpenoic acids
  作者：Dominique Cahard、Malika Mammeri、Jean-Marie Poirier、Lucette Duhamel

  DOI：10.1016/s0040-4039(00)00457-3

  日期：2000.5

  A three-step synthesis of (2Z), (4E)-polyenic acids 6 is described. Condensation of aldehydes 1 with potassium prenal enolate led to dihydropyranols 3 which were oxidized into dihydropyrones 5, precursors of (2Z), (4E)-polyenic acids 6. The procedure was applied to a synthesis of 13-cis-retinoic acids from beta-ionylidene acetaldehydes. (C) 2000 Elsevier Science Ltd. All rights reserved.