2-[1-Furan-2-yl-meth-(E)-ylidene]-4-methyl-3-oxo-pentanoic acid 2,2,6,6-tetramethyl-piperidin-1-yl ester | 878494-69-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 2-[1-Furan-2-yl-meth-(E)-ylidene]-4-methyl-3-oxo-pentanoic acid 2,2,6,6-tetramethyl-piperidin-1-yl ester
• 英文别名: (2,2,6,6-tetramethylpiperidin-1-yl) (2E)-2-(furan-2-ylmethylidene)-4-methyl-3-oxopentanoate
• CAS: 878494-69-0
• 化学式: C₂₀H₂₉NO₄
• 分子量: 347.455
• InChiKey: FTVGWENVCWBLEE-DTQAZKPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  59.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[1-Furan-2-yl-meth-(E)-ylidene]-4-methyl-3-oxo-pentanoic acid 2,2,6,6-tetramethyl-piperidin-1-yl ester 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 0.25h， 以72%的产率得到2-[1-Furan-2-yl-meth-(E)-ylidene]-3-hydroxy-4-methyl-pentanoic acid 2,2,6,6-tetramethyl-piperidin-1-yl ester
  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：

  3-Hydroxy-4-methyl-pentanoic acid 2,2,6,6-tetramethyl-piperidin-1-yl ester 在 哌啶 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 0.33h， 生成 2-[1-Furan-2-yl-meth-(E)-ylidene]-4-methyl-3-oxo-pentanoic acid 2,2,6,6-tetramethyl-piperidin-1-yl ester
  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

文献信息

• <i>E</i>- or <i>Z</i>-Selective Knoevenagel Condensation of Acetoacetic Derivatives:  Effect of Acylated Substituent, that is, TEMPO and Amines, as an Auxiliary, and New Accesses to Trisubstituted <i>E</i>- and <i>Z</i>-2-Alkenals and Furans
  作者：Tsutomu Inokuchi、Hiroyuki Kawafuchi

  DOI：10.1021/jo051952w

  日期：2006.2.1

  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.