N,N-diethylhex-4-ynamide | 51578-07-5

• 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-diethylhex-4-ynamide
• CAS: 51578-07-5
• 化学式: C₁₀H₁₇NO
• 分子量: 167.251
• InChiKey: VRBSZCXZFBQRMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N-diethylhex-4-ynamide 在 正丁基锂 、 N-cyclohexyl-2,6-diisopropylaniline 、 zinc(II) chloride 、 bis(η3-allyl-μ-chloropalladium(II)) 、 乙酸烯丙酯 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 5.0h， 以86%的产率得到(E)-N,N-diethylhex-2-en-4-ynamide
  参考文献：
  名称：

  Amide α,β-Dehydrogenation Using Allyl-Palladium Catalysis and a Hindered Monodentate Anilide

  摘要：

  A practical and direct method for the alpha,beta-dehydrogenation of amides is reported using allyl-palladium catalysis. Critical to the success of this process was the synthesis and application of a novel lithium N-cyclohexyl anilide (LiCyan). The reaction conditions tolerate a wide variety of substrates, including those with acidic heteroatom nucleophiles.

  DOI：

  10.1021/jacs.5b12924
• 作为产物：
  描述：

  N,N-二乙基乙酰胺 、 1-溴-2-丁炔 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 12.5h， 以88%的产率得到N,N-diethylhex-4-ynamide
  参考文献：
  名称：

  Amide α,β-Dehydrogenation Using Allyl-Palladium Catalysis and a Hindered Monodentate Anilide

  摘要：

  A practical and direct method for the alpha,beta-dehydrogenation of amides is reported using allyl-palladium catalysis. Critical to the success of this process was the synthesis and application of a novel lithium N-cyclohexyl anilide (LiCyan). The reaction conditions tolerate a wide variety of substrates, including those with acidic heteroatom nucleophiles.

  DOI：

  10.1021/jacs.5b12924

文献信息

• 1,7-substituted heptyne-2-ones
  申请人：MARION MERRELL DOW INC.

  公开号：EP0251126A2

  公开（公告）日：1988-01-07

  1-phenyl-1-hydroxy or fluoro-hept-5-yn-2-ones substituted with a C₁ to C₇ alkyl, C₃ to C₆ cycloalkyl, aryl, heteroaryl or heterocycloalkyl group at the 1-position and an amino, a dialkylamino, piperidyl, a pyrrolidyl or a hexahydroazepinyl group at the 7-position are disclosed. The preferred compounds are, 1-cyclohexyl-1-phenyl-1-­hydroxy-7-dimethylaminohept-5-yn-2-one, 1-cyclohexyl-1-­phenyl-1-hydroxy-7-methylaminohept-5-yn-2-one and 1-­cyclohexyl-1-phenyl-1-hydroxy-7-ethylaminohept-5-yn-2-one. The compounds are highly specific M₁-AChR antago­nists with relatively prolonged duration of activity. They are particularly useful in the treatment of neurogenic blad­der disorders.

  本发明公开了在 1-位上被 C₁ 至 C₇ 烷基、C₃ 至 C₆ 环烷基、芳基、杂芳基或杂环烷基以及在 7-位上被氨基、二烷基氨基、哌啶基、吡咯烷基或六氢氮杂卓基取代的 1-苯基-1-羟基或氟化庚-5-炔-2-酮。优选的化合物有：1-环己基-1-苯基-1-羟基-7-二甲基氨基庚-5-炔-2-酮、1-环己基-1-苯基-1-羟基-7-甲基氨基庚-5-炔-2-酮和 1-环己基-1-苯基-1-羟基-7-乙基氨基庚-5-炔-2-酮。 这些化合物是高度特异性的 M₁-AChR 拮抗剂，活性持续时间相对较长。它们特别适用于治疗神经源性膀胱疾病。
• Amide α,β-Dehydrogenation Using Allyl-Palladium Catalysis and a Hindered Monodentate Anilide
  作者：Yifeng Chen、Aneta Turlik、Timothy R. Newhouse

  DOI：10.1021/jacs.5b12924

  日期：2016.2.3

  A practical and direct method for the alpha,beta-dehydrogenation of amides is reported using allyl-palladium catalysis. Critical to the success of this process was the synthesis and application of a novel lithium N-cyclohexyl anilide (LiCyan). The reaction conditions tolerate a wide variety of substrates, including those with acidic heteroatom nucleophiles.