4-methyl-2-[(1E,3E)-2-methyl-4-phenylbuta-1,3-dienyl]-3,6-dihydro-2H-pyran-6-ol | 214463-55-5

• 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-2-[(1E,3E)-2-methyl-4-phenylbuta-1,3-dienyl]-3,6-dihydro-2H-pyran-6-ol
• CAS: 214463-55-5
• 化学式: C₁₇H₂₀O₂
• 分子量: 256.345
• InChiKey: YAYPBTLTACRBEA-PEGOPYGQSA-N

物化性质

• 沸点：
  416.7±45.0 °C(Predicted)
• 密度：
  1.130±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-methyl-2-[(1E,3E)-2-methyl-4-phenylbuta-1,3-dienyl]-3,6-dihydro-2H-pyran-6-ol 在 吡啶盐酸盐 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 0.08h， 以88%的产率得到
  参考文献：
  名称：

  Regioselective addition of the prenal potassium dienolate onto α,β-unsaturated aldehydes. A short access to polyenaldehydes

  摘要：

  The potassium dienolate of prenal obtained by treatment of the corresponding dienoxysilane with tBuOK was reacted with enaldehydes. In all cases a gamma-specific reaction occurs. According to the reaction conditions gamma;1,2 or a gamma;1,4 coupled product was selectively obtained with enals. The gamma;1,2 reaction provided an efficient prenylation procedure. A short two-step synthesis of retinal is described. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01544-5
• 作为产物：
  描述：

  (2E,4E)-3-methyl-5-phenylpenta-2,4-dienal 、 (E)-trimethyl((3-methylbuta-1,3-dien-1-yl)oxy)silane 在 potassium tert-butylate 作用下， 生成 4-methyl-2-[(1E,3E)-2-methyl-4-phenylbuta-1,3-dienyl]-3,6-dihydro-2H-pyran-6-ol
  参考文献：
  名称：

  Regioselective addition of the prenal potassium dienolate onto α,β-unsaturated aldehydes. A short access to polyenaldehydes

  摘要：

  The potassium dienolate of prenal obtained by treatment of the corresponding dienoxysilane with tBuOK was reacted with enaldehydes. In all cases a gamma-specific reaction occurs. According to the reaction conditions gamma;1,2 or a gamma;1,4 coupled product was selectively obtained with enals. The gamma;1,2 reaction provided an efficient prenylation procedure. A short two-step synthesis of retinal is described. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01544-5

文献信息

• Prenylation Reaction Performed with Catalytically Generated Potassium Prenal Dienolate
  作者：Dominique Cahard、Lucette Duhamel、Sandrine Lecomte、Jean-Marie Poirier

  DOI：10.1055/s-1998-1955

  日期：1998.12

  A new prenylation method based on the reaction of catalytically generated potassium dienolate of prenal with α,β-unsaturated aldehydes is described. The reaction is highly regioselective, via a γ-1,2-addition, and provides an efficient route to retinal.

  本文介绍了一种新的预炔化方法，该方法基于催化生成的预炔二烯酸钾与δ、δ²-不饱和醛的反应。该反应通过δ-1,2-加成具有高度的区域选择性，并提供了获得视黄醛的有效途径。