(2,2,6,6-tetramethylpiperidin-1-yl) (2Z)-2-[[1-(4-methylphenyl)sulfonylindol-3-yl]methylidene]-3-oxobutanoate | 878494-88-3

• 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: (2,2,6,6-tetramethylpiperidin-1-yl) (2Z)-2-[[1-(4-methylphenyl)sulfonylindol-3-yl]methylidene]-3-oxobutanoate
• CAS: 878494-88-3
• 化学式: C₂₉H₃₄N₂O₅S
• 分子量: 522.665
• InChiKey: PKACMHQMHXNYLO-BWAHOGKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  94.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2,2,6,6-tetramethylpiperidin-1-yl) (2Z)-2-[[1-(4-methylphenyl)sulfonylindol-3-yl]methylidene]-3-oxobutanoate 在 三甲基铝 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (2,2,6,6-tetramethylpiperidin-1-yl) (2E)-2-[[1-(4-methylphenyl)sulfonylindol-3-yl]methylidene]-3-oxobutanoate
  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：

  1-acetoxy-2,2,6,6-tetramethylpiperidine 在 哌啶 、 溶剂黄146 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 5.33h， 生成 (2,2,6,6-tetramethylpiperidin-1-yl) (2Z)-2-[[1-(4-methylphenyl)sulfonylindol-3-yl]methylidene]-3-oxobutanoate
  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