1-(4-methoxybenzyloxy)-2-(2-propyl)-2-propene | 148675-55-2

• 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: 1-(4-methoxybenzyloxy)-2-(2-propyl)-2-propene
• 英文别名: Benzene, 1-methoxy-4-[(3-methyl-2-methylenebutoxy)methyl]-；1-methoxy-4-[(3-methyl-2-methylidenebutoxy)methyl]benzene
• CAS: 148675-55-2
• 化学式: C₁₄H₂₀O₂
• 分子量: 220.312
• InChiKey: GQMZJZXQBFWQDR-UHFFFAOYSA-N

物化性质

• 沸点：
  296.0±20.0 °C(Predicted)
• 密度：
  0.956±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-methoxybenzyloxy)-2-(2-propyl)-2-propene 在 咪唑 、 sodium hydroxide 、 四氯化锡 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 10.08h， 生成 ethyl (2S)-2-<(t-butyldimethylsilyl)oxy>-4-<(4-methoxybenzyloxy)methyl>-5-methyl-4-hexenoate
  参考文献：
  名称：

  紫杉醇A环系统的新合成。

  摘要：

  光学活性紫杉醇A-环单元3由2-异丙基-2-丙烯醇以11个步骤合成。立体异构中心通过不对称乙醛酸-烯反应和Sharpless不对称环氧化反应引入。

  DOI：

  10.1016/s0040-4020(01)86347-x
• 作为产物：
  描述：

  2-isopropylallyl alcohol 、 4-甲氧基氯苄 在 sodium hydride 作用下， 生成 1-(4-methoxybenzyloxy)-2-(2-propyl)-2-propene
  参考文献：
  名称：

  紫杉醇A环系统的新合成。

  摘要：

  光学活性紫杉醇A-环单元3由2-异丙基-2-丙烯醇以11个步骤合成。立体异构中心通过不对称乙醛酸-烯反应和Sharpless不对称环氧化反应引入。

  DOI：

  10.1016/s0040-4020(01)86347-x

文献信息

• Rearrangement of p-methoxybenzyl-protected allylic alcohols to aldehydes
  作者：Johan Wennerberg、Lars Eklund、Magnus Polla、Torbjörn Frejd

  DOI：10.1039/a608020k

  日期：——

  Allyl p-methoxybenzyl ethers undergo an acid-catalysed 1,4-rearrangement to give p-methoxyphenylbutyraldehyde derivatives, which can be ring-closed to give substituted naphthalene derivatives.

  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。
• 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.
• Siamyl Glyoxylate as an Efficient Enophile in the Lewis Acid Mediated Glyoxylate Ene-Reaction with Allylic Ethers. Application to the Synthesis of a Taxol A-Ring Subunit
  作者：Johan Wennerberg、Magnus Polla、Torbjörn Frejd

  DOI：10.1021/jo971082l

  日期：1997.12.1

  In contrast to other simple alkyl glyoxylates, siamyl glyoxylate (la) proved to be an effective enophile in the glyoxylate ene-reaction with the allylic ether 2a, which we earlier used for the synthesis of the A-ring subunit of taxol.
• 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).
• Zeolite β-Induced Rearrangement of Alkoxybenzyl Allyl Ethers to Aldehydes and Ketones. 5.¹ Variation of the Allylic Moiety
  作者：Johan Wennerberg、Charlotte Olofsson、Torbjörn Frejd

  DOI：10.1021/jo972243o

  日期：1998.5.1

  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.