1Z,3E-1-(4-methoxybenzyloxy)-4-methoxybuta-1,3-diene | 478554-61-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1Z,3E-1-(4-methoxybenzyloxy)-4-methoxybuta-1,3-diene
• 英文别名: 1-methoxy-4-[[(1Z,3E)-4-methoxybuta-1,3-dienoxy]methyl]benzene
• CAS: 478554-61-9
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: YYOUWZBYVTZFPR-DCFDNNIBSA-N

物化性质

• 沸点：
  348.4±32.0 °C(Predicted)
• 密度：
  1.037±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1Z,3E-1-(4-methoxybenzyloxy)-4-methoxybuta-1,3-diene 在 吡啶 、 咪唑 、 四氧化锇 、 对苯二酚 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 20.0~50.0 ℃ 、1200.02 MPa 条件下， 反应 76.0h， 生成
  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
• 作为产物：
  描述：

  E-4-bromobut-2-enal dimethyl acetal 在 叔丁基锂 、 potassium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 1Z,3E-1-(4-methoxybenzyloxy)-4-methoxybuta-1,3-diene
  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.