5,6-Dihydro-4-methyl-6-(2-phenylethenyl)-2H-pyran-2-one | 134641-64-8

• 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: 5,6-Dihydro-4-methyl-6-(2-phenylethenyl)-2H-pyran-2-one
• 英文别名: 4-methyl-6-[(E)-2-phenylethenyl]-5,6-dihydro-2H-pyran-2-one；4-methyl-2-[(E)-2-phenylethenyl]-2,3-dihydropyran-6-one
• CAS: 134641-64-8
• 化学式: C₁₄H₁₄O₂
• 分子量: 214.264
• InChiKey: HGRFQOOMXRJTQM-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  5,6-Dihydro-4-methyl-6-(2-phenylethenyl)-2H-pyran-2-one 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以75%的产率得到3-methyl-7t-phenyl-hepta-2c,4t,6-trienoic 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：

  (E)-4-methyl-6-styryl-5,6-dihydro-2H-pyran-2-ol 在 chromium(VI) oxide 、 硫酸 作用下， 以 水 、 丙酮 为溶剂， 以90%的产率得到5,6-Dihydro-4-methyl-6-(2-phenylethenyl)-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

• [3 + n] Annulation Reactions by Means of 3-Trimethylstannyl-2-[(trimethylstannyl)methyl]propene, an Isobutene Dianion Synthetic Equivalent
  作者：Alessandro Degl'Innocenti、Pasquale Dembech、Alessandro Mordini、Alfredo Ricci、Giancarlo Seconi

  DOI：10.1055/s-1991-26441

  日期：——

  Stepwise functionalization of the two carbon-tin bonds in 3-trimethylstannyl-2-[(trimethylstannyl)methyl]propene with electrophiles (diacyl dichlorides or aldehydes and carbon dioxide, provides a promising route for [3 + n] annulation reactions.

  3- 三甲基锡-2-[(三甲基锡)甲基]丙烯中的两个碳-锡键与亲电体（二酰二氯或醛和二氧化碳）的逐步官能化为 [3 + n] 环化反应提供了一条很有前景的途径。
• α,β-Unsaturated β-Methyl-δ-lactones in Nitrile Oxide Cycloaddition Reactions. Synthesis of Saturated Lactones and Lactams
  作者：I. V. Mineyeva

  DOI：10.1134/s1070428022060033

  日期：2022.6

  Abstract New isoxazoline derivatives have been synthesized in high yields by cycloaddition of acetonitrile oxide to α,β-unsaturated β-methyl-δ-lactones. These unsaturated lactones have been used to obtain β-methyl branched saturated lactones and lactams, as well as lactones with an inversed configuration of hydroxy group, following the divergent approach.

  摘要 通过将氧化乙腈环加成到 α,β-不饱和 β-甲基-δ-内酯上，以高收率合成了新的异恶唑啉衍生物。这些不饱和内酯已被用于获得β-甲基支链饱和内酯和内酰胺，以及具有反相羟基构型的内酯，遵循发散的方法。
• 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.