(E)-5-(allyloxy)-4,4-bis(allyloxymethyl)pent-2-enal | 960149-62-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-5-(allyloxy)-4,4-bis(allyloxymethyl)pent-2-enal
• 英文别名: (E)-5-prop-2-enoxy-4,4-bis(prop-2-enoxymethyl)pent-2-enal
• CAS: 960149-62-6
• 化学式: C₁₆H₂₄O₄
• 分子量: 280.364
• InChiKey: HFVKDIHUVWTXIP-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-5-(allyloxy)-4,4-bis(allyloxymethyl)pent-2-enal 、 苄胺 在 triazolium salt 咪唑 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以90%的产率得到5-(allyloxy)-4,4-bis(allyloxymethyl)-N-benzylpentanamide
  参考文献：
  名称：

  N-Heterocyclic Carbene-Catalyzed Redox Amidations of α-Functionalized Aldehydes with Amines

  摘要：

  A catalytic method for the direct synthesis of carboxylic acid amides from amines and alpha-functionalized aldehydes is possible through the synergistic role of a N-heterocyclic carbene catalyst and imidazole, affording amides via activated carboxylates catalytically generated via an internal redox reaction of the aldehyde substrates. The use of imidazole or other N-heterocycles as an additive is essential to overcoming imine formation and serves as a uniquely reactive substrate for the generation of an acyl imidazolium intermediate that is converted to the final amide product.

  DOI：

  10.1021/ja0768136
• 作为产物：
  描述：

  (E)-5-allyloxy-4,4-bis(allyloxymethyl)pent-2-en-1-ol 在 四丙基高钌酸铵 、 4 A molecular sieve 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以60%的产率得到(E)-5-(allyloxy)-4,4-bis(allyloxymethyl)pent-2-enal
  参考文献：
  名称：

  从enals催化生成活化的羧酸盐：决定碱的产物的作用。

  摘要：

  由咪唑鎓或三唑鎓盐和碱原位生成的N-杂环碳氧烷与烯醛反应，导致催化生成均烯酸酯。这些中间体的命运取决于催化碱：强碱（如（t）BuOK）会导致碳-碳键的形成，而较弱的碱则会使均烯酸酯质子化并随后生成活化的羧酸酯。这一发现，再加上新型三唑鎓预催化剂的设计，使烯类能够进行催化，原子经济的氧化还原酯化反应。[反应：看文字]

  DOI：

  10.1021/ol051269w

文献信息

• N-Heterocyclic Carbene-Catalyzed Redox Amidations of α-Functionalized Aldehydes with Amines
  作者：Jeffrey W. Bode、Stephanie S. Sohn

  DOI：10.1021/ja0768136

  日期：2007.11.1

  A catalytic method for the direct synthesis of carboxylic acid amides from amines and alpha-functionalized aldehydes is possible through the synergistic role of a N-heterocyclic carbene catalyst and imidazole, affording amides via activated carboxylates catalytically generated via an internal redox reaction of the aldehyde substrates. The use of imidazole or other N-heterocycles as an additive is essential to overcoming imine formation and serves as a uniquely reactive substrate for the generation of an acyl imidazolium intermediate that is converted to the final amide product.
• Catalytic Generation of Activated Carboxylates from Enals:  A Product-Determining Role for the Base
  作者：Stephanie S. Sohn、Jeffrey W. Bode

  DOI：10.1021/ol051269w

  日期：2005.9.1

  from imidazolium or triazolium salts and bases react with enals, leading to the catalytic generation of homoenolates. The fate of these intermediates is determined by the catalytic base: strong bases such as (t)BuOK lead to carbon-carbon bond formation, while weaker bases allow protonation of the homoenolate and subsequent generation of activated carboxylates. This discovery, along with the design of a

  由咪唑鎓或三唑鎓盐和碱原位生成的N-杂环碳氧烷与烯醛反应，导致催化生成均烯酸酯。这些中间体的命运取决于催化碱：强碱（如（t）BuOK）会导致碳-碳键的形成，而较弱的碱则会使均烯酸酯质子化并随后生成活化的羧酸酯。这一发现，再加上新型三唑鎓预催化剂的设计，使烯类能够进行催化，原子经济的氧化还原酯化反应。[反应：看文字]