N-benzyl 2,4-dimethylpenta-2,3-dienamide | 463930-77-0

• 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-benzyl 2,4-dimethylpenta-2,3-dienamide
• 英文别名: N-benzyl-2,4-dimethylpenta-2,3-dienamide
• CAS: 463930-77-0
• 化学式: C₁₄H₁₇NO
• 分子量: 215.295
• InChiKey: BWVXKWWPMYPRRM-UHFFFAOYSA-N

物化性质

• 沸点：
  411.3±28.0 °C(Predicted)
• 密度：
  0.982±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.81
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  29.1
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  N-benzyl 2,4-dimethylpenta-2,3-dienamide 在 potassium carbonate 、 sodium iodide 、 palladium dichloride 作用下， 以 异丁酰胺 为溶剂， 反应 14.0h， 以88%的产率得到2,2'-bis(benzylimino)-3,5,5,3',5',5'-hexamethyl-2,5,2',5'-tetrahydro[4,4']bifuranyl
  参考文献：
  名称：

  Homodimeric coupling–cyclization reaction of 2,3-allenamides

  摘要：

  The PdCl2/Nal/K2CO3-catalyzed highly stereoselective homodimeric coupling-cyclization reaction of 2,3-allenamides afforded Z-bis(furanimine) derivatives. The addition of K2CO3 is crucial for this reaction and a possible mechanism is proposed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.03.083
• 作为产物：
  描述：

  2,4-dimethyl-2,3-pentadienoic acid 、 苄胺 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以45%的产率得到N-benzyl 2,4-dimethylpenta-2,3-dienamide
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jo025967v

文献信息

• Amide-Controlled Highly Selective Catalytic Borylcupration of Allenes
  作者：Weiming Yuan、Xue Zhang、Yihua Yu、Shengming Ma

  DOI：10.1002/chem.201202835

  日期：2013.5.27

  A novel copper‐catalyzed, highly regio‐ and stereoselective borylcupration of substituted 2,3‐allenamides with bis(pinacolato)diboron producing Z‐β‐borylated β,γ‐unsaturated enoamides has been demonstrated. Due to the unique effect of the amide‐group, perfect regio‐ and stereoselectivity and good to excellent yields have been achieved, which were rationalized by a DFT study.

  已经证明了一种新型的铜催化的，取代的2,3-丙二酰胺与双（频哪醇）二硼生成Z -β硼化的β，γ-不饱和烯酰胺的铜催化的，高区域和立体选择性的硼取代。由于酰胺基团的独特作用，已实现了完美的区域选择性和立体选择性以及良好至优异的收率，这通过DFT研究得以合理化。
• A facile synthesis of β-allenyl furanimines via Pd-catalyzed cyclization of 2,3-allenamides with propargylic carbonates
  作者：Guofei Chen、Ya Zhang、Chunling Fu、Shengming Ma

  DOI：10.1016/j.tet.2011.01.041

  日期：2011.3

  The Pd(OAc)(2)/TFP-catalyzed cyclization reaction of 2,3-allenamides in the presence of propargylic carbonates provides an efficient route to beta-allenyl furanimine derivatives. Preliminary mechanistic study showed that this reaction was probably initiated by Pd(0) species. (C) 2011 Elsevier Ltd. All rights reserved.
• 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.
• Study on halolactamization-γ-hydroxylation or haloiminolactonization of 2,3-alkadienamides
  作者：Shengming Ma、Hexin Xie

  DOI：10.1016/j.tet.2004.10.050

  日期：2005.1

  The reactions of 4-mono- or 4-unsubstituted 2,3-alkadienamides with CuX2 afforded 5-hydroxypyrTol-2(5H)-ones via the sequential lactamization and gamma-hydroxylation process in aqueous THF while those of 4,4-disubstituted 2,3-alkadienamides with CuX2 in THF afforded iminolactones in high yields. Iodoiminolactonization and iodolactamization/gamma-hydroxylation were achieved by the corresponding reaction with I-2 in THF at rt. The structures of the products depend on the steric hindrance at the 4-position of the starting allenamides. Relatively electron-rich allenes afforded the corresponding products in much higher yields under milder reaction conditions implying the intramolecular electrophilic nature of the cyclization reaction. (C) 2004 Elsevier Ltd. All rights reserved.
• 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.