E-4-(4-methoxybenzyloxy)-3-methylbut-2-enal dimethyl acetal

• 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: E-4-(4-methoxybenzyloxy)-3-methylbut-2-enal dimethyl acetal
• 英文别名: 1-[[(E)-4,4-dimethoxy-2-methylbut-2-enoxy]methyl]-4-methoxybenzene
• 化学式: C₁₅H₂₂O₄
• 分子量: 266.337
• InChiKey: WOBZCTVJQHYVBN-FMIVXFBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  cis-1,2-cyclopentanediol 、 E-4-(4-methoxybenzyloxy)-3-methylbut-2-enal dimethyl acetal 在 camphor-10-sulfonic acid 、 2,2-二甲氧基丙烷 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以64%的产率得到2-[3-(4-methoxybenzyloxy)-2-methylprop-1-enyl]tetrahydrocyclopenta[1,3]dioxolane
  参考文献：
  名称：

  Synthesis of α,β-unsaturated dioxanes, dioxolanes and dioxepanes by trans-acetalisation of dimethylacetals with meso or C2-symmetrical 1,2-, 1,3- and 1,4-diols

  摘要：

  Several o-dibenzylic diols were prepared reacting organometallics with o-phthalaldehyde at room temperature in ether. The identity of the meso and C-2-symmetrical (D,L) isomers as well as their ratio were determined by chiral gas chromatography. The meso and C-2 (racemic) stereoisomeric diols were easily separated by flash chromatography on silica gel. A set of 18 alpha,beta-unsaturated acetals were then prepared reacting those, as well as commercially available 1,2, 1,3 and 1,4 diols, with the corresponding methylacetals in acidic medium. A trans-acetalisation procedure adapted to the cases of fragile allylic alcohols or unfavorable 1,6 diols-derived dioxonanes based on a Dean-Stark trapping of methanol was also employed. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.11.009
• 作为产物：
  描述：

  (E/Z)-4-bromo-1,1-dimethoxy-3-methylbut-2-ene 、 4-甲氧基苄醇 在 potassium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 Z-4-(4-methoxybenzyloxy)-3-methylbut-2-enal dimethyl acetal 、 E-4-(4-methoxybenzyloxy)-3-methylbut-2-enal dimethyl acetal
  参考文献：
  名称：

  Thermal/Hyperbaric Heterocycloaddition of 1,4-Dialkoxy-1,3-dienes:  The de novo (E,Z) Way to Sugars

  摘要：

  1-(Z)-Alkoxy-4-(E)-methoxybutadiene derivatives have been reacted with ethylgyoxylate and diethyl ketomalonate under thermal or hyperbaric conditions. They provide, with a total regioselectivity and fair to total endoselectivities, the expected dihydropyranic cycloadducts. Three of those pseudoglycals have been converted in a few classical steps (deprotection, reduction, and dihydroxylation) into (racemic) allose, mannose, and gullose derivatives. The order of these three steps has a direct influence on the efficiency of the transformation and determines the stereochemistry of the final sugar.

  DOI：

  10.1021/jo0204193

文献信息

• Thermal/Hyperbaric Heterocycloaddition of 1,4-Dialkoxy-1,3-dienes:  The <i>de novo</i> (<i>E</i>,<i>Z</i>) Way to Sugars
  作者：Carole Bataille、Gautier Bégin、Anne Guillam、Loïc Lemiègre、Caroline Lys、Jacques Maddaluno、Loïc Toupet

  DOI：10.1021/jo0204193

  日期：2002.11.1

  1-(Z)-Alkoxy-4-(E)-methoxybutadiene derivatives have been reacted with ethylgyoxylate and diethyl ketomalonate under thermal or hyperbaric conditions. They provide, with a total regioselectivity and fair to total endoselectivities, the expected dihydropyranic cycloadducts. Three of those pseudoglycals have been converted in a few classical steps (deprotection, reduction, and dihydroxylation) into (racemic) allose, mannose, and gullose derivatives. The order of these three steps has a direct influence on the efficiency of the transformation and determines the stereochemistry of the final sugar.
• Synthesis of α,β-unsaturated dioxanes, dioxolanes and dioxepanes by trans-acetalisation of dimethylacetals with meso or C2-symmetrical 1,2-, 1,3- and 1,4-diols
  作者：Loı̈c Lemiègre、Fleur Lesetre、Jean-Claude Combret、Jacques Maddaluno

  DOI：10.1016/j.tet.2003.11.009

  日期：2004.1

  Several o-dibenzylic diols were prepared reacting organometallics with o-phthalaldehyde at room temperature in ether. The identity of the meso and C-2-symmetrical (D,L) isomers as well as their ratio were determined by chiral gas chromatography. The meso and C-2 (racemic) stereoisomeric diols were easily separated by flash chromatography on silica gel. A set of 18 alpha,beta-unsaturated acetals were then prepared reacting those, as well as commercially available 1,2, 1,3 and 1,4 diols, with the corresponding methylacetals in acidic medium. A trans-acetalisation procedure adapted to the cases of fragile allylic alcohols or unfavorable 1,6 diols-derived dioxonanes based on a Dean-Stark trapping of methanol was also employed. (C) 2003 Elsevier Ltd. All rights reserved.