(2Z)-2-(furan-2-ylmethylidene)-N-methoxy-N-methyl-3-(oxan-2-yloxy)butanamide | 878494-80-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (2Z)-2-(furan-2-ylmethylidene)-N-methoxy-N-methyl-3-(oxan-2-yloxy)butanamide
• CAS: 878494-80-5
• 化学式: C₁₆H₂₃NO₅
• 分子量: 309.362
• InChiKey: NDFHWDHVTAKQDC-KAMYIIQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  61.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2Z)-2-(furan-2-ylmethylidene)-N-methoxy-N-methyl-3-(oxan-2-yloxy)butanamide 在 lithium aluminium tetrahydride 作用下， 反应 0.17h， 以72%的产率得到(Z)-3-(2-furyl)-2-(1-tetrahydropyranyloxyethyl)-2-propenal
  参考文献：
  名称：

  E- or Z-Selective Knoevenagel Condensation of Acetoacetic Derivatives:  Effect of Acylated Substituent, that is, TEMPO and Amines, as an Auxiliary, and New Accesses to Trisubstituted E- and Z-2-Alkenals and Furans

  摘要：

  Knoevenagel condensation of O-acetoacetylTEMPOs (2,2,6,6-tetramethylpiperidine-1-oxyl) with aldehydes substituted with an electron-withdrawing group such as aromatic and heteroaromatic ones leads preferentially to E-adducts, while acylacetoamides including Weinreb amides produce Z-adducts, exclusively. These E- and Z-adducts are selectively converted to the corresponding (2E)- and (2Z)-2hyroxyalkyl-2-alkenals, respectively, by stepwise reductions of the acyl group with DIBALH and then the carboxylic functions after protection of the hydroxy group. Transformation of the Knoevenagel products by taking advantage of the E-geometry to trisubstituted furans is also developed.

  DOI：

  10.1021/jo051952w
• 作为产物：
  描述：

  N-甲氧基-N-甲基-3-氧代丁酰胺 在 哌啶 、 4-甲基苯磺酸吡啶 、 二异丁基氢化铝 、 溶剂黄146 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 48.25h， 生成 (2Z)-2-(furan-2-ylmethylidene)-N-methoxy-N-methyl-3-(oxan-2-yloxy)butanamide
  参考文献：
  名称：

  E- or Z-Selective Knoevenagel Condensation of Acetoacetic Derivatives:  Effect of Acylated Substituent, that is, TEMPO and Amines, as an Auxiliary, and New Accesses to Trisubstituted E- and Z-2-Alkenals and Furans

  摘要：

  Knoevenagel condensation of O-acetoacetylTEMPOs (2,2,6,6-tetramethylpiperidine-1-oxyl) with aldehydes substituted with an electron-withdrawing group such as aromatic and heteroaromatic ones leads preferentially to E-adducts, while acylacetoamides including Weinreb amides produce Z-adducts, exclusively. These E- and Z-adducts are selectively converted to the corresponding (2E)- and (2Z)-2hyroxyalkyl-2-alkenals, respectively, by stepwise reductions of the acyl group with DIBALH and then the carboxylic functions after protection of the hydroxy group. Transformation of the Knoevenagel products by taking advantage of the E-geometry to trisubstituted furans is also developed.

  DOI：

  10.1021/jo051952w