4-methyl-6-(4-nitrophenyl)-5,6-dihydro-2H-pyran-2-one | 1042165-46-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-methyl-6-(4-nitrophenyl)-5,6-dihydro-2H-pyran-2-one
• 英文别名: 4-Methyl-2-(4-nitrophenyl)-2,3-dihydropyran-6-one
• CAS: 1042165-46-7
• 化学式: C₁₂H₁₁NO₄
• 分子量: 233.224
• InChiKey: ILJFQVYFPIYWOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 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：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methyl-6-(4-nitrophenyl)-5,6-dihydro-2H-pyran-2-one 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以65%的产率得到(2Z,4E)-3-Methyl-5-(2-nitro-phenyl)-penta-2,4-dienoic acid
  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：

  4-Methyl-6-(2-nitro-phenyl)-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4-methyl-6-(4-nitrophenyl)-5,6-dihydro-2H-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

• Exploiting the Anders–Gaßner variant on the Wittig reaction: new methodology for the synthesis of 3,3-dimethylacroyl enol esters
  作者：Brett D. Schwartz、Craig M. Williams、Ernst Anders、Paul V. Bernhardt

  DOI：10.1016/j.tet.2008.04.068

  日期：2008.6

  A one pot synthesis of the 3,3-dimethylacroyl enol ester function found in the vibsane type diterpenes has been developed based on the Anders-Gassner variant of the Wittig reaction (AGW reaction). This method uses easily accessible acyloxyalkylidene phosphoranes and a variety of aldehydes. (c) 2008 Elsevier Ltd. All rights reserved.