N-benzyl-4-phenyl-2,3-pentadienamide | 827302-78-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-benzyl-4-phenyl-2,3-pentadienamide
• 英文别名: N-benzyl-4-phenylpenta-2,3-dienamide
• CAS: 827302-78-3
• 化学式: C₁₈H₁₇NO
• 分子量: 263.339
• InChiKey: UYBGMYUWQOMNCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.56
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  羰基硫 、 N-benzyl-4-phenyl-2,3-pentadienamide 在 C₁₅H₁₈N₂OS 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以98%的产率得到
  参考文献：
  名称：

  Access to 1,3-oxazine-2,4-diones/1,3-thiazine-2,4-diones via organocatalytic CO₂/COS incorporation into allenamides

  摘要：

  Lewis碱-CO₂/COS加合物首次被研究作为有机催化剂，用于CO₂/COS与亚砜烯酰胺的[4 + 2]环化反应，选择性合成1,3-噁唑-2,4-二酮/1,3-噻唑-2,4-二酮。

  DOI：

  10.1039/c9ob02398d
• 作为产物：
  描述：

  1-溴-3-苯基-1,2-丁二烯 、 一氧化碳 、 苄胺 在 四(三苯基膦)钯 三乙胺 作用下， 以 四氢呋喃 为溶剂， 20.0 ℃ 、1.82 MPa 条件下， 反应 1.5h， 以71%的产率得到N-benzyl-4-phenyl-2,3-pentadienamide
  参考文献：
  名称：

  Study on halolactamization-γ-hydroxylation or haloiminolactonization of 2,3-alkadienamides

  摘要：

  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.

  DOI：

  10.1016/j.tet.2004.10.050

文献信息

• 一种有机催化剂催化羰基硫转化合成噻嗪二 酮杂环化合物的方法
  申请人：大连理工大学

  公开号：CN109180607B

  公开（公告）日：2021-04-16

  本发明提供一种有机催化剂催化羰基硫转化合成噻嗪二酮杂环化合物的方法，属于有机合成、农药及医药化工合成技术领域。该方法是在高压釜中加入联烯酰胺类化合物原料和溶剂，加入氮杂环卡宾、氮杂极性烯烃或其与羰基硫的加合物作为有机催化剂，通入羰基硫气体，在60～100摄氏度条件下搅拌12小时，反应结束后冷却至室温，缓慢释放未反应的羰基硫气体，抽干溶剂得粗产品，经柱层析纯化得到1,3‑噻嗪‑2,4‑二酮类化合物。本发明使用羰基硫代替传统硫源，该反应具有清洁，反应条件温和，高官能团耐受性，高转化率和立体选择性特点，在有机合成、农药及医药中具有广泛用途。
• 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 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.
• Access to 1,3-oxazine-2,4-diones/1,3-thiazine-2,4-diones <i>via</i> organocatalytic CO₂/COS incorporation into allenamides
  作者：Hui Zhou、Rui Wang、Hui Zhang、Wei Chen、Xiao-Bing Lu

  DOI：10.1039/c9ob02398d

  日期：——

  Lewis base-CO₂/COS adducts were firstly studied as organocatalysts for [4 + 2] annulation of CO₂/COS with allenamides to selectively synthesize 1,3-oxazine-2,4-diones/1,3-thiazine-2,4-diones.

  Lewis碱-CO₂/COS加合物首次被研究作为有机催化剂，用于CO₂/COS与亚砜烯酰胺的[4 + 2]环化反应，选择性合成1,3-噁唑-2,4-二酮/1,3-噻唑-2,4-二酮。
• 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.