N,N-dimethyl-3-oxohept-6-enamide | 419567-33-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N,N-dimethyl-3-oxohept-6-enamide
• CAS: 419567-33-2
• 化学式: C₉H₁₅NO₂
• 分子量: 169.224
• InChiKey: YGJCJFTVFNQQPO-UHFFFAOYSA-N

物化性质

• 沸点：
  270.2±23.0 °C(Predicted)
• 密度：
  0.974±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl-3-oxohept-6-enamide 在 双(乙腈)氯化钯(II) poly(ethylene glycol) 400 、 copper dichloride 作用下， 反应 25.0h， 以94%的产率得到2-氧代环己烷羧酸二甲酰胺
  参考文献：
  名称：

  Efficient and Reusable PdCl₂(MeCN)₂/CuCl₂/PEG-400 System for Cyclization of Alkenyl β-Keto Esters and Amides

  摘要：

  PEG-400 [poly(ethylene glycol-400)] was found as an effective medium for the PdCl(2)(MeCN)(2)-catalyzed hydroalkylation cyclization of alkenyl beta-keto esters and amides. In PEG-400, no additives such as Me(3)SiCl and Ln(OTf)(3) were required for the complete conversion of alkenyl beta-keto esters. The results also showed that CuCl(2) could promote the reaction. In the presence of PdCl(2)(MeCN)(2), CuCl(2), and PEG-400, various alkenyl beta-keto esters and amides underwent a selective cyclization reaction to give good to excellent yields of the desired six-membered-ring carbocycles. Furthermore, the PdCl(2)(MeCN)(2)/CuCl(2)/PEG-400 system could be recycled and reused five times without any loss of catalytic activity.

  DOI：

  10.1021/jo0506635
• 作为产物：
  描述：

  N,N-二甲基乙酰基乙酰胺 、 3-溴丙烯 在 六甲基磷酰三胺 、 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.0h， 以82%的产率得到N,N-dimethyl-3-oxohept-6-enamide
  参考文献：
  名称：

  路易斯酸促进了苯基硒烯基转移串联自由基的环化反应。

  摘要：

  [反应：见正文]开发了一种新的路易斯酸促进的苯硒基转移串联自由基自由基化方法。在路易斯酸（例如Yb（OTf）3或Mg（ClO4）2）的存在下，在低温（-45摄氏度）的光解条件下，各种不饱和α-苯基硒基β-酮酰胺进行自由基环化反应以生成单环或高效，区域选择性和立体选择性的双环产物。

  DOI：

  10.1021/ol025750n

文献信息

• Enantio- and Diastereoselective Intermolecular Stetter Reaction of Glyoxamide and Alkylidene Ketoamides
  作者：Qin Liu、Tomislav Rovis

  DOI：10.1021/ol901081a

  日期：2009.7.2

  A triazolinylidene carbene catalyzed intermolecular Stetter reaction of glyoxamide and alkylidene ketoamides has been developed. 1,4-Dicarbonyl products are afforded in good to excellent yields, enantioselectivities, and diastereoselectivities. Further derivatization of the products affords useful intermediates for organic synthesis.
• Lanthanide Triflate-Promoted Palladium-Catalyzed Cyclization of Alkenyl β-Keto Esters and Amides
  作者：Dan Yang、Jin-Heng Li、Qiang Gao、Yi-Long Yan

  DOI：10.1021/ol0349110

  日期：2003.8.1

  graphicsLanthanide triflates were found to promote the palladium-catalyzed cyclization of alkenyl beta-keto esters and amides. In the presence of catalytic amounts of PdCl2(MeCN)(2) and Ln(OTf)(3), various alkenyl beta-keto esters and amides underwent regioselective cyclization reactions to give six-, seven-, or eight-membered-ring carbocycles in moderate to excellent yields.
• Lewis Acid Promoted Phenylseleno Group Transfer Tandem Radical Cyclization Reactions
  作者：Dan Yang、Qiang Gao、On-Yi Lee

  DOI：10.1021/ol025750n

  日期：2002.4.1

  [reaction: see text] A new Lewis acid promoted phenylseleno group transfer tandem radical cyclization method was developed. In the presence of Lewis acids such as Yb(OTf)3 or Mg(ClO4)2, under photolysis condition at low temperature (-45 degrees C), various unsaturated alpha-phenylseleno beta-keto amides underwent radical cyclization reactions to give monocyclic or bicyclic products in a highly efficient

  [反应：见正文]开发了一种新的路易斯酸促进的苯硒基转移串联自由基自由基化方法。在路易斯酸（例如Yb（OTf）3或Mg（ClO4）2）的存在下，在低温（-45摄氏度）的光解条件下，各种不饱和α-苯基硒基β-酮酰胺进行自由基环化反应以生成单环或高效，区域选择性和立体选择性的双环产物。
• Efficient and Reusable PdCl₂(MeCN)₂/CuCl₂/PEG-400 System for Cyclization of Alkenyl <i>β</i>-Keto Esters and Amides
  作者：Jin-Heng Li、Qi-Ming Zhu、Yun Liang、Dan Yang

  DOI：10.1021/jo0506635

  日期：2005.6.1

  PEG-400 [poly(ethylene glycol-400)] was found as an effective medium for the PdCl(2)(MeCN)(2)-catalyzed hydroalkylation cyclization of alkenyl beta-keto esters and amides. In PEG-400, no additives such as Me(3)SiCl and Ln(OTf)(3) were required for the complete conversion of alkenyl beta-keto esters. The results also showed that CuCl(2) could promote the reaction. In the presence of PdCl(2)(MeCN)(2), CuCl(2), and PEG-400, various alkenyl beta-keto esters and amides underwent a selective cyclization reaction to give good to excellent yields of the desired six-membered-ring carbocycles. Furthermore, the PdCl(2)(MeCN)(2)/CuCl(2)/PEG-400 system could be recycled and reused five times without any loss of catalytic activity.