4-(4-methoxyphenyl)-2-(2-propyl)butanal | 189366-70-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(4-methoxyphenyl)-2-(2-propyl)butanal
• 英文别名: 2-[2-(4-Methoxyphenyl)ethyl]-3-methylbutanal
• CAS: 189366-70-9
• 化学式: C₁₄H₂₀O₂
• 分子量: 220.312
• InChiKey: QREXXQFZQWQLDF-UHFFFAOYSA-N

物化性质

• 沸点：
  325.5±25.0 °C(Predicted)
• 密度：
  0.971±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  4-(4-methoxyphenyl)-2-(2-propyl)butanal 在 PPA 作用下， 以75%的产率得到2-Isopropyl-7-methoxy-naphthalene
  参考文献：
  名称：

  Rearrangement of p-methoxybenzyl-protected allylic alcohols to aldehydes

  摘要：

  对甲氧基苄基烯丙基醚在酸催化下进行 1，4-重排，生成对甲氧基苯基丁醛衍生物，这些衍生物可以环闭，生成取代的萘衍生物。

  DOI：

  10.1039/a608020k
• 作为产物：
  描述：

  2-isopropylallyl alcohol 在 Zeolite β 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.5h， 生成 4-(4-methoxyphenyl)-2-(2-propyl)butanal
  参考文献：
  名称：

  Zeolite β-Induced Rearrangement of Alkoxybenzyl Allyl Ethers to Aldehydes and Ketones. 5.¹ Variation of the Allylic Moiety

  摘要：

  Allylic PMB ethers rearranged in the presence of zeolite beta to form 4-arylbutanals or 5-arylpentanones depending on the substituent pattern of the allylic moiety. Best results were obtained with substrates carrying simple substituents in the allylic 2-position, but a couple of substrates lacking a 2-substituent also rearranged. More functionalized substituents in this position were not tolerated. A propargyl PMB ether and a homoallylic PMB ether rearranged as well, but the products were mixtures of isomeric olefins. The 4-arylbutanals 2c and 2e and the 5-arylpentanone 2j were cyclized in PPA to give naphthalene and dihydronaphthalene derivatives, respectively.

  DOI：

  10.1021/jo972243o

文献信息

• Mechanistic Aspects of the Zeolite beta Induced Rearrangement of Alkoxybenzyl Allyl Ethers to Aldehydes and Ketones.
  作者：Johan Wennerberg、Torbjörn Frejd、Anny Jutand、Larry L. Miller、Giovanni V. Sebastiani、George W. Francis、József Szúnyog、Bengt Långström

  DOI：10.3891/acta.chem.scand.52-0095

  日期：——

  The mechanism for the novel zeolite beta catalyzed rearrangement of alkoxybenzyl allyl ethers to aldehydes and ketones has been investigated by use of cross reactions and deuterium labeling. The reaction is mainly intramolecular and may be described as a nucleophilic attack of the double bond on the electrophilic benzylic carbon of the ether-Lewis acid complex, followed by a 1,2-hydride (or alkyl) migration.
• Zeolite beta Induced Rearrangement of Alkoxybenzyl Allyl Ethers to Aldehydes and Ketones. Part IV. Investigation of the Reaction Conditions.
  作者：Johan Wennerberg、Charlotte Olofsson、Torbjörn Frejd、William R. Salaneck、Reijo Sillanpää、Gábor Bernáth、József Szúnyog、Bengt Långström

  DOI：10.3891/acta.chem.scand.52-0232

  日期：——

  The reaction conditions for the rearrangement of p-methoxybenzyl allyl ether 1 have been investigated with respect to catalysts and solvents. Zeolite beta was the best catalyst but zeolite Y and mordenite were also effective. The Lewis acids BF3 . OEt2, (iPrO)(2)TiCl2, and AlMe2Cl induced the rearrangment but were considerably less efficient than the solid catalysts. Protic acids were not very useful owing to the formation of too many products. Among the solvents tested dichloromethane and 1,1,2-trichloroethane were the most useful even though the rearrangement took place in several other solvents. Interestingly, 1 rearranged spontaneously on dissolution in 1,1,1,3,3,3-hexafluoropropan-2-ol (HFP).