N-(1-(4-cyanophenyl)vinyl)acetamide | 823790-72-3

• 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-(1-(4-cyanophenyl)vinyl)acetamide
• 英文别名: N-[1-(4-Cyanophenyl)ethenyl]acetamide
• CAS: 823790-72-3
• 化学式: C₁₁H₁₀N₂O
• mdl: MFCD09033630
• 分子量: 186.213
• InChiKey: YLILOFLECOVRJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(1-(4-cyanophenyl)vinyl)acetamide 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以51 mg的产率得到对氰基苯乙酮
  参考文献：
  名称：

  Fast and Regioselective Heck Couplings with N-Acyl-N-vinylamine Derivatives

  摘要：

  Highly regioselective Heck couplings of aryl triflates with N-acyl-N-vinylamines lacking an N-alkyl substituent were achieved with reaction times of approximately 1 h in yields ranging from 62 to 98% using 1.5 mol % of Pd-2(dba)(3), 3 mol % of DPPF, and diethylisopropylamine in dioxane. The efficiency of these cross-couplings were studied with several N-vinylamides and an example each of an N-vinylcarbamate and an N-vinylurea. The Heck coupling products easily underwent acidic hydrolysis to the corresponding aryl methyl ketone or in situ hydrogenation in the presence of (Ph3P)(3)RhCl under a hydrogen atmosphere to provide the N-acyl derivatives of pharmaceutically relevant benzylic amines. The coupling of a vinyl triflate and more interestingly a vinyl tosylate to N-vinyl acetamide was also studied affording a 2-acylamino-1,3-butadiene with the same high regioselectivity in preference for the alpha-isomer. This result suggests that Heck couplings of electron-rich alkenes with vinyl tosylates also follow a cationic pathway.

  DOI：

  10.1021/jo050669u
• 作为产物：
  描述：

  对氰基苯乙酮 在 盐酸羟胺 、 sodium acetate 、 铁粉 、 溶剂黄146 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 2.0h， 生成 N-(1-(4-cyanophenyl)vinyl)acetamide
  参考文献：
  名称：

  Rhodium(iii)-catalyzed olefinic C–H alkynylation of enamides at room temperature

  摘要：

  报告了Rh（III）催化的烯酰胺的C-H烯烃炔基化反应，用于立体特异性构建具有合成用途的Z型烯炔酰胺。该方案显示出良好的官能团容忍性和操作简便性，从而为轻松获取特定的1,3-炔烯衍生物提供了另一种合成机会。

  DOI：

  10.1039/c4cc04072d

文献信息

• Synthesis of Functionalized Vinylsilanes via Metal-Free Dehydrogenative Silylation of Enamides
  作者：Xi-Hao Chang、Zi-Lu Wang、Meng Zhao、Chao Yang、Jie-Jun Li、Wei-Wei Ma、Yun-He Xu

  DOI：10.1021/acs.orglett.9b04645

  日期：2020.2.21

  A novel method of metal-free dehydrogenative silylation of enamides has been developed. The desired functionalized vinylsilane products were obtained in moderate to good yield and with high stereoselectivities. This protocol displays good tolerance of various functionalities. Furthermore, the high chemoselectivity of this reaction enables us to introduce different unsaturated C-C moieties to the products

  已开发出一种新型的酰胺类无金属脱氢甲硅烷基化方法。以中等至良好的产率和高的立体选择性获得了所需的官能化乙烯基硅烷产物。该协议显示出对各种功能的良好耐受性。此外，该反应的高化学选择性使我们能够向产物中引入不同的不饱和CC部分。产品进一步衍生为其他有用化合物的难易程度也证明了当前方法的高度合成效用。
• Direct Enamido C(sp²)−H Diphosphorylation Enabled by a PCET‐Triggered Double Radical Relay: Access to<i>gem</i>‐Bisphosphonates
  作者：Hao‐Qiang Cao、Hao‐Nan Liu、Zhe‐Yuan Liu、Bao‐Kun Qiao、Fa‐Guang Zhang、Jun‐An Ma

  DOI：10.1002/chem.202000517

  日期：2020.4.24

  electron-transfer (PCET)-triggered enamido C(sp2 )-H diphosphorylation. This reaction represents a rare example of realizing the challenging double C-P bond formation at a single carbon atom, thus providing facile access to a broad variety of structurally diverse bisphosphonates from simple enamides under silver-mediated conditions. Initial mechanistic studies demonstrated that the diphosphorylation involves

  在这里，我们报告通过质子耦合电子转移（PCET）触发的烯键式C（sp2）-H双磷酸化来构造有价值的gem-BP的新颖而直接的协议。该反应代表了一个难得的例子，该例子实现了在单个碳原子上形成具有挑战性的双CP键，从而在银介导的条件下轻松地从简单的酰胺中获得了多种结构多样的双膦酸酯。初步的机理研究表明，二磷酸化涉及两轮PCET引发的自由基中继过程。
• Rhodium(III)-Catalyzed Direct C–H Arylation of Various Acyclic Enamides with Arylsilanes
  作者：Xiaolan Li、Kai Sun、Wenjuan Shen、Yong Zhang、Ming-Zhu Lu、Xuzhong Luo、Haiqing Luo

  DOI：10.1021/acs.orglett.0c03578

  日期：2021.1.1

  The stereoselective β-C(sp2)–H arylation of various acyclic enamides with arylsilanes via Rh(III)-catalyzed cross-coupling reaction was illustrated. The methodology was characterized by extraordinary efficacy and stereoselectivity, a wide scope of substrates, good functional group tolerance, and the adoption of environmentally friendly arylsilanes. The utility of this present method was evidenced by

  通过Rh（III）催化的交叉偶联反应，说明了各种无环酰胺与芳基硅烷的立体选择性β-C（sp 2）-H芳基化反应。该方法的特点是非凡的功效和立体选择性，广泛的底物范围，良好的官能团耐受性以及采用环保的芳基硅烷。该方法的实用性由克级合成和产物的进一步精制证明。此外，Rh（III）催化的C–H活化被认为是反应机理中的关键步骤。
• Versatile Pyrrole Synthesis through Ruthenium(II)-Catalyzed Alkene C–H Bond Functionalization on Enamines
  作者：Lianhui Wang、Lutz Ackermann

  DOI：10.1021/ol303224e

  日期：2013.1.4

  An efficient ruthenium(II) catalyst enabled broadly applicable oxidative alkyne annulations with electron-rich enamines to provide diversely decorated pyrroles, even in an aerobic fashion with air as the ideal oxidant.

  高效的钌（II）催化剂使带有富电子的烯胺的广泛应用的氧化炔烃环化反应能够提供装饰多样的吡咯，即使是在有氧的情况下，以空气作为理想氧化剂也是如此。
• The ruthenium-catalyzed C–H functionalization of enamides with isocyanates: easy entry to pyrimidin-4-ones
  作者：Pengfei Shi、Song Li、Lu-Min Hu、Cong Wang、Teck-Peng Loh、Xu-Hong Hu

  DOI：10.1039/c9cc03612a

  日期：——

  Ruthenium-catalyzed heteroannulation between enamides and isocyanates has been realized as a complementary approach to conventional strategies for the synthesis of pyrimidin-4-ones. High step- and atom-economy was achieved for the rapid construction of such privileged scaffolds, which are found in a multitude of pharmaceutical compounds. The generality and practicability of this transformation were

  钌催化的酰胺和异氰酸酯之间的异环化反应已作为常规方法合成嘧啶丁4-酮的补充方法而实现。为了快速构建这种特权的支架，实现了高度的步骤和原子经济性，这种特权的支架可在多种药物化合物中找到。这种转化的普遍性和实用性反映在具有各种官能团，大规模合成和后期多样化的底物的广泛范围内。