3-methyl-2-butenal-bis(para-methoxy)benzyl acetal | 1438427-63-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-methyl-2-butenal-bis(para-methoxy)benzyl acetal
• 英文别名: 1-Methoxy-4-[[1-[(4-methoxyphenyl)methoxy]-3-methylbut-2-enoxy]methyl]benzene；1-methoxy-4-[[1-[(4-methoxyphenyl)methoxy]-3-methylbut-2-enoxy]methyl]benzene
• CAS: 1438427-63-4
• 化学式: C₂₁H₂₆O₄
• 分子量: 342.435
• InChiKey: WHXANDDPAXRHOF-UHFFFAOYSA-N

物化性质

• 沸点：
  453.7±40.0 °C(Predicted)
• 密度：
  1.070±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-methyl-2-butenal-bis(para-methoxy)benzyl acetal 在 叔丁基锂 作用下， 以 正戊烷 为溶剂， 反应 2.0h， 以76%的产率得到p-methoxybenzyl 3-methylbuta-1,3-dienyl ether
  参考文献：
  名称：

  A Mild PPTS-Catalyzed Acetalization of α,β-Unsaturated Aldehydes: The First Single-Step Protocol towards Benzylic Acetals

  摘要：

  A mild and convenient procedure for the synthesis of highly sensitive benzylic acetals from alpha,beta-unsaturated aldehydes and the corresponding benzylic alcohols is reported. The new method provides a single-step access to these compounds for the first time. The applications of pyridinium p-toluenesulfonate (PPTS) as a very mild Bronsted acid catalyst and 5 angstrom molecular sieves (MS) as the dehydrating agent were found to be essential. Furthermore, an application of the acetals in the synthesis of 1-functionalized dienes is exemplified.

  DOI：

  10.1055/s-0032-1318169
• 作为产物：
  描述：

  3-甲基-2-丁烯醛 、 4-甲氧基苄醇 在 4-甲基苯磺酸吡啶 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以87%的产率得到3-methyl-2-butenal-bis(para-methoxy)benzyl acetal
  参考文献：
  名称：

  A Mild PPTS-Catalyzed Acetalization of α,β-Unsaturated Aldehydes: The First Single-Step Protocol towards Benzylic Acetals

  摘要：

  A mild and convenient procedure for the synthesis of highly sensitive benzylic acetals from alpha,beta-unsaturated aldehydes and the corresponding benzylic alcohols is reported. The new method provides a single-step access to these compounds for the first time. The applications of pyridinium p-toluenesulfonate (PPTS) as a very mild Bronsted acid catalyst and 5 angstrom molecular sieves (MS) as the dehydrating agent were found to be essential. Furthermore, an application of the acetals in the synthesis of 1-functionalized dienes is exemplified.

  DOI：

  10.1055/s-0032-1318169

文献信息

• A Mild PPTS-Catalyzed Acetalization of α,β-Unsaturated Aldehydes: The First Single-Step Protocol towards Benzylic Acetals
  作者：Jörg Pietruszka、Dietrich Böse、Marvin Lübcke

  DOI：10.1055/s-0032-1318169

  日期：——

  A mild and convenient procedure for the synthesis of highly sensitive benzylic acetals from alpha,beta-unsaturated aldehydes and the corresponding benzylic alcohols is reported. The new method provides a single-step access to these compounds for the first time. The applications of pyridinium p-toluenesulfonate (PPTS) as a very mild Bronsted acid catalyst and 5 angstrom molecular sieves (MS) as the dehydrating agent were found to be essential. Furthermore, an application of the acetals in the synthesis of 1-functionalized dienes is exemplified.