diethyl 4-cyano-3-oxopentane-1,1-dicarboxylate

• 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: diethyl 4-cyano-3-oxopentane-1,1-dicarboxylate
• 英文别名: Diethyl 2-(3-cyano-2-oxobutyl)propanedioate
• 化学式: C₁₂H₁₇NO₅
• 分子量: 255.271
• InChiKey: IOPRKUNSJBWLOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  93.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-丁炔-2-酮 、 diethyl 4-cyano-3-oxopentane-1,1-dicarboxylate 在 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 0.17h， 以46%的产率得到diethyl (2R*,3R*)-3-cyano-3-methyl-2-(2-oxopropyl)-4-cyclopentanone-1,1-dicarboxylate
  参考文献：
  名称：

  [n + 1] Annulation Route to Highly Substituted Cyclic Ketones with Pendant Ketone, Nitrile, and Ester Functionality

  摘要：

  Two carbon acids connected by a tether containing a ketone undergo two Michael reactions to 3-butyn-2-one to afford highly substituted and functionalized cyclic ketones with pendant ketone, nitrile, and ester functionality. The stereochemical courses of the double Michael reactions vary remarkably with the structure of the starting material. Double Michael adducts with equatorially disposed cyano groups can be hydrogenated to afford trans-fused bicyclic amines.

  DOI：

  10.1021/jo9907787
• 作为产物：
  描述：

  1,1,2-乙烷三羧酸三乙酯 、 丙腈 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以61%的产率得到diethyl 4-cyano-3-oxopentane-1,1-dicarboxylate
  参考文献：
  名称：

  [n + 1] Annulation Route to Highly Substituted Cyclic Ketones with Pendant Ketone, Nitrile, and Ester Functionality

  摘要：

  Two carbon acids connected by a tether containing a ketone undergo two Michael reactions to 3-butyn-2-one to afford highly substituted and functionalized cyclic ketones with pendant ketone, nitrile, and ester functionality. The stereochemical courses of the double Michael reactions vary remarkably with the structure of the starting material. Double Michael adducts with equatorially disposed cyano groups can be hydrogenated to afford trans-fused bicyclic amines.

  DOI：

  10.1021/jo9907787

文献信息

• [<i>n</i> + 1] Annulation Route to Highly Substituted Cyclic Ketones with Pendant Ketone, Nitrile, and Ester Functionality
  作者：Robert B. Grossman、Dhananjay S. Pendharkar、Brian O. Patrick

  DOI：10.1021/jo9907787

  日期：1999.9.1

  Two carbon acids connected by a tether containing a ketone undergo two Michael reactions to 3-butyn-2-one to afford highly substituted and functionalized cyclic ketones with pendant ketone, nitrile, and ester functionality. The stereochemical courses of the double Michael reactions vary remarkably with the structure of the starting material. Double Michael adducts with equatorially disposed cyano groups can be hydrogenated to afford trans-fused bicyclic amines.