4-methylpenta-2,3-dienamide | 54129-73-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-methylpenta-2,3-dienamide
• CAS: 54129-73-6
• 化学式: C₆H₉NO
• 分子量: 111.144
• InChiKey: HEONAPQZZCSEMP-UHFFFAOYSA-N

物化性质

• 熔点：
  122 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  264.5±13.0 °C(Predicted)
• 密度：
  0.922±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.59
• 重原子数：
  8.0
• 可旋转键数：
  1.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.09
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  4-methylpenta-2,3-dienamide 在 溶剂黄146 、 sodium iodide 作用下， 反应 4.0h， 以87%的产率得到3-Iodo-4-methyl-3-pentenamide
  参考文献：
  名称：

  Ma; Xie; Wang, Synthesis, 2001, # 5, p. 713 - 730

  摘要：

  DOI：
• 作为产物：
  描述：

  4-methyl-2,3-pentadienenitrile 在 sodium hydroxide 、 双氧水 作用下， 以 乙醇 为溶剂， 生成 4-methylpenta-2,3-dienamide
  参考文献：
  名称：

  Synthesis and reactions of allenic amides

  摘要：

  DOI：

  10.1016/s0040-4020(01)97258-8

文献信息

• Sur une voie d'acces commode aux aldehydes, cetones et amides α-alleniques.
  作者：M Bertrand、G Gil、J Viala

  DOI：10.1016/s0040-4039(01)93601-9

  日期：1979.1

  α-allenic aldehydes, ketones or amides are easily prepared from 1,1-bisubstituted α-allenic alcohols by nickel peroxide oxidation.

  α-烯醛，酮或酰胺很容易通过过氧化镍氧化反应由1,1-双取代的α-烯醇制得。
• Steric Hindrance-Controlled Pd(0)-Catalyzed Coupling−Cyclization of 2,3-Allenamides and Organic Iodides. An Efficient Synthesis of Iminolactones and γ-Hydroxy-γ-lactams
  作者：Shengming Ma、Hexin Xie

  DOI：10.1021/jo025967v

  日期：2002.9.1

  Under the catalysis of 1 mol % Pd(PPh3)(4), the reaction of 4,4-disubstituted 2,3-allenamides and organic iodides in toluene afforded iminolactones stereospecifically in >90% yields using K2CO3 (2 equiv)-5 mol % TBAB as the base. A similar reaction with 4-monosubstituted 2,3-allenamides afforded gamma-hydroxy-gamma-lactams in relatively lower yields. The N/O-attack selectivity may be determined by the steric effect at the 4-position of 2,3-allenamides.
• A Novel Synthesis of 1,3-Oxazine-2,4-diones via a Simple and Efficient Reaction of CO₂ with 2,3-Allenamides
  作者：Guofei Chen、Chunling Fu、Shengming Ma

  DOI：10.1021/ol9009046

  日期：2009.7.2

  A simple and efficient reaction of CO2 with 2,3-allenamides under mild conditions (CO2 balloon without any metal catalyst in the presence of K2CO3 or Cs2CO3) leads to an efficient synthesis of 1,3-oxazine-2,4-diones. The high reactivity of the allene moiety is crucial for the success of this transformation since the corresponding reaction of alpha,beta-unsaturated alkenamides or alkynamides does not occur.
• Pd(CH₃CN)₂Cl₂-Catalyzed Oxidative Heterodimerization Reaction of 2,3-Allenamides and 1,2-Allenyl Ketones:  An Efficient Synthesis of 4-(Furan-3‘-yl)-2(5<i>H</i>)-furanimines
  作者：Shengming Ma、Zhenhua Gu、Zhanqian Yu

  DOI：10.1021/jo0507441

  日期：2005.8.1

  The Pd(II)-catalyzed oxidative heterodimerization reaction of 2,3-allenamides and 1,2-allenyl ketones was studied. It provides an efficient route for the synthesis of the polysubstituted 4-(furan-3'-yl)2(5H)-furanimines, which are not readily available from the known methods. Due to the application of benzoquinone, the loadings of both the palladium catalyst and ketone have been greatly reduced for the oxidative heterodimerization of 2,3-allenamides and 1,2-allenyl ketones in acetic acid.
• BERTRAND M.; GIL G.; VIALA J., TETRAHEDRON LETT., 1979, NO 18, 1595-1598
  作者：BERTRAND M.、 GIL G.、 VIALA J.

  DOI：——

  日期：——