N-benzyl-N-(cyclohexen-1-yl)-2-methylprop-2-enamide | 143818-17-1

• 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-N-(cyclohexen-1-yl)-2-methylprop-2-enamide
• CAS: 143818-17-1
• 化学式: C₁₇H₂₁NO
• 分子量: 255.36
• InChiKey: PFSLTSSAQWZHCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 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-benzyl-N-(cyclohexen-1-yl)-2-methylprop-2-enamide 、 丙二酸二甲酯 在 四丁基醋酸铵 作用下， 以 乙腈 为溶剂， 以54 %的产率得到dimethyl 2-((1-benzyl-3-methyl-2-oxo-2,3,4,5,6,7-hexahydro-1H-indol-3-yl)methyl)malonate
  参考文献：
  名称：

  通过电化学诱导 3-氮杂-1,5-二烯和 1,3-二羰基化合物脱氢区域选择性环化合成多种 4-吡咯啉-2-酮

  摘要：

  提出了一种无催化剂、无金属、无氧化剂的电化学脱氢区域选择性环化，用于从 3-氮杂-1,5-二烯和 1,3-二羰基化合物合成 4-吡咯啉-2-酮。该方法提供了广泛的底物兼容性，并且可以轻松扩展到克级。

  DOI：

  10.1002/ejoc.202301246
• 作为产物：
  描述：

  环己酮 、 alkaline earth salt of/the/ methylsulfuric acid 在 三乙胺 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 4.0h， 生成 N-benzyl-N-(cyclohexen-1-yl)-2-methylprop-2-enamide
  参考文献：
  名称：

  Formation of 1,2,3,4-tetrahydro-2-pyridones by aza-annulation of imines with acrylate derivatives

  摘要：

  The aza-annulation of imines with activated acrylate derivatives was studied as a means of preparing the corresponding 1,2,3,4-tetrahydro-2-pyridones. Through the use of reagents known to facilitate the formation of amide bonds from carboxylic acids, several methods of activating the acrylate species were compared. The acrylate derivatives studied were acryloyl chloride and acrylic anhydride as well as acrylic acid activated by reaction with EtO2CCl, (PhO)2P(O)N3, or MCPI. Optimum annulation was obtained with imines derived from cyclohexanone to produce octahydro-2-quinolone products. The N-isobutylimine prepared from cyclopentanone also produced selective ring annulation to efficiently produce the corresponding bicyclic product, but the reaction with the imine of n-butanal produced lower yields of cyclic product. Ring formation was relatively unaffected by substituents at the a-position of the acrylate derivative, demonstrated by the use of methacrylate, but beta-substituents hindered the annulation process and, in turn, increased the amounts of byproduct resulting from only N-acylation of the imine. Increasing the steric bulk of the imine alkyl substituent produced the opposite effect; the relative amount of N-acylation compared to complete aza-annulation was diminished as the size of the substituent was increased. Mechanistic features of the reaction are discussed in terms of product distribution and competition experiments.

  DOI：

  10.1021/jo00046a011

文献信息

• Photoinduced Regioselective Perfluoroalkylation/Cyclization Cascade of 3‐Aza‐1,5‐Dienes: Access to Pentasubstituted 3‐Perfluoroalkyl‐1,3‐Dihydropyrrol‐2‐Ones
  作者：Ruihan Yang、Danna Chen、Shiyi Lin、Xuege Yang、Lou Shi、Qiaowen Chang、Deqiang Liang

  DOI：10.1002/ejoc.202300528

  日期：2023.8.14

  A visible light‐induced perfluoroalkylative cyclization of 3‐aza‐1,5‐dienes leading to pentasubstituted 1,3‐dihydropyrrole‐2‐ones is presented. The reaction is regiospecific, for the radical adds across the acrylamido moiety, whereas the enaminic double bond functions as a built‐in radical trap. It could be carried out on a 2‐gram scale, and the sunlight is a usable light source. Other virtues of the protocol include a short reaction time, a low catalyst loading, mild conditions and a broad substrate scope.

  摘要 介绍了一种可见光诱导的 3-氮杂-1,5-二烯全氟化烷基环化反应，从而生成五取代的 1,3-二氢吡咯-2-酮。该反应具有区域特异性，因为自由基会穿过丙烯酰胺基，而烯酰胺双键则起着内置自由基陷阱的作用。该反应可以在 2 克的规模上进行，而且阳光是一种可用的光源。该方案的其他优点还包括反应时间短、催化剂负载量低、条件温和以及底物范围广。
• Photoredox/nickel dual-catalysis-enabled synthesis of N-heterocycles from alkyl chlorides and alkenes
  作者：Xuege Yang、Lou Shi、Ruoyu Qin、Minglin Tao、Qin Feng、Xiao-Yong Chang、Qiaowen Chang、Deqiang Liang

  DOI：10.1016/j.mcat.2023.113806

  日期：2024.1

  A photoredox/nickel dual catalysis is presented for the construction of several kinds of useful nitrogen-containing heterocycles. This protocol is regioselective and features a broad substrate scope. It provides a direct access to nitrogen-containing heterocycles by reacting alkyl chlorides with readily available activated and unactivated alkenes. Moreover, this protocol can be easily scalable to a

  提出了光氧化还原/镍双重催化用于构建几种有用的含氮杂环。该协议具有区域选择性，并具有广泛的底物范围。它通过使烷基氯与容易获得的活化和未活化的烯烃反应，提供了直接获得含氮杂环的方法。此外，该协议可以轻松扩展到克级，并且使用太阳光作为光源是可行的。机理研究表明能量转移途径参与催化过程。
• Formation of 1,2,3,4-tetrahydro-2-pyridones by aza-annulation of imines with acrylate derivatives
  作者：K. Paulvannan、John R. Stille

  DOI：10.1021/jo00046a011

  日期：1992.9

  The aza-annulation of imines with activated acrylate derivatives was studied as a means of preparing the corresponding 1,2,3,4-tetrahydro-2-pyridones. Through the use of reagents known to facilitate the formation of amide bonds from carboxylic acids, several methods of activating the acrylate species were compared. The acrylate derivatives studied were acryloyl chloride and acrylic anhydride as well as acrylic acid activated by reaction with EtO2CCl, (PhO)2P(O)N3, or MCPI. Optimum annulation was obtained with imines derived from cyclohexanone to produce octahydro-2-quinolone products. The N-isobutylimine prepared from cyclopentanone also produced selective ring annulation to efficiently produce the corresponding bicyclic product, but the reaction with the imine of n-butanal produced lower yields of cyclic product. Ring formation was relatively unaffected by substituents at the a-position of the acrylate derivative, demonstrated by the use of methacrylate, but beta-substituents hindered the annulation process and, in turn, increased the amounts of byproduct resulting from only N-acylation of the imine. Increasing the steric bulk of the imine alkyl substituent produced the opposite effect; the relative amount of N-acylation compared to complete aza-annulation was diminished as the size of the substituent was increased. Mechanistic features of the reaction are discussed in terms of product distribution and competition experiments.
• Synthesis of Diverse 4‐Pyrrolin‐2‐ones by Electrochemically Induced Dehydrogenative Regioselective Cyclization of 3‐Aza‐1,5‐dienes and 1,3‐Dicarbonyl Compounds
  作者：Xing Ji、Run He、Lou Shi、Shaoguang Sun、Deqiang Liang

  DOI：10.1002/ejoc.202301246

  日期：2024.3.18

  A catalyst-free, metal-free, and oxidizing-agent-free electrochemical dehydrogenative regioselective cyclization for the synthesis of 4-pyrrolin-2-ones from 3-aza-1,5-dienes and 1,3-dicarbonyl compounds is presented. This method offers a wide range of substrate compatibility and can be readily scaled up to the gram scale.

  提出了一种无催化剂、无金属、无氧化剂的电化学脱氢区域选择性环化，用于从 3-氮杂-1,5-二烯和 1,3-二羰基化合物合成 4-吡咯啉-2-酮。该方法提供了广泛的底物兼容性，并且可以轻松扩展到克级。