(E)-ethyl 3-[2-(N,N-dimethylcarbamoyl)phenyl]acrylate | 1373338-23-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-ethyl 3-[2-(N,N-dimethylcarbamoyl)phenyl]acrylate
• 英文别名: N,N-dimethyl-2-[(E)-(ethoxycarbonyl)ethenyl]benzamide；ethyl (E)-3-(2-(dimethylcarbamoyl)phenyl)acrylate；ethyl (E)-3-[2-(dimethylcarbamoyl)phenyl]acrylate；ethyl (E)-3-[2-(dimethylcarbamoyl)phenyl]prop-2-enoate
• CAS: 1373338-23-8
• 化学式: C₁₄H₁₇NO₃
• 分子量: 247.294
• InChiKey: OGDYOOSVBSEJKI-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  丙烯酸乙酯 、 N,N-二甲基苯甲酰胺 在 silver hexafluoroantimonate 、 tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 作用下， 以 氯苯 为溶剂， 以65%的产率得到(E)-ethyl 3-[2-(N,N-dimethylcarbamoyl)phenyl]acrylate
  参考文献：
  名称：

  铑和光氧还原催化结合用于C ？芳烃的H功能化：可见光的氧化Heck反应

  摘要：

  芳烃的直接，氧化金属催化的CH官能化在合成有机化学中很重要。通常，在这些反应中必须使用（化学计量）过量的有机或无机氧化剂。铑和光氧化还原催化与可见光的结合可以使芳烃直接进行CH烯化反应。少量（1摩尔％）的光氧化还原催化剂可在温和的条件下有效地对多种底物进行有效的CH功能化。

  DOI：

  10.1002/anie.201400560

文献信息

• Synthesis of Phthalides through Tandem Rhodium-Catalyzed C-H Olefination and Annulation of Benzamides
  作者：Neeraj Kumar Mishra、Jihye Park、Miji Choi、Satyasheel Sharma、Hyeim Jo、Taejoo Jeong、Sangil Han、Saegun Kim、In Su Kim

  DOI：10.1002/ejoc.201600368

  日期：2016.6

  The rhodium(III)-catalyzed tandem C–H olefination and cyclization of benzamides with various alkenes is described. This protocol provides direct access to highly substituted phthalides, which are known as crucial frameworks of biologically active compounds. In particular, the amide directing group containing a benzimidazole group facilitates the activation of aromatic ortho-C–H bonds leading to olefination

  描述了铑 (III) 催化的串联 C-H 烯化和苯甲酰胺与各种烯烃的环化。该协议提供了对被称为生物活性化合物的关键框架的高度取代的苯酞的直接访问。特别是，含有苯并咪唑基团的酰胺导向基团促进芳族邻-C-H键的活化，导致烯化中间体，并迅速转化为酸部分，可以进一步进行分子内环化过程。
• Ru/Ag-Catalyzed Oxidative Alkenylation of Benzamides and Phenylazoles through Regioselective C–H Bond Cleavage
  作者：Yuto Hashimoto、Timon Ortloff、Koji Hirano、Tetsuya Satoh、Carsten Bolm、Masahiro Miura

  DOI：10.1246/cl.2012.151

  日期：2012.2.5

  Oxidative alkenylation of N,N-disubstituted benzamides with alkenes accompanied by regioselective C–H bond cleavage proceeds efficiently in the presence of a Ru/Ag catalyst system together with a copper oxidant. The procedure is also applicable to phenylazoles.

  在 Ru/Ag 催化剂体系和铜氧化剂的作用下，N,N-二取代苯甲酰胺与烯的氧化烯化反应以及区域选择性 C-H 键裂解反应得以高效进行。该过程也适用于苯基唑。
• Combining Rhodium and Photoredox Catalysis for CH Functionalizations of Arenes: Oxidative Heck Reactions with Visible Light
  作者：David C. Fabry、Jochen Zoller、Sadiya Raja、Magnus Rueping

  DOI：10.1002/anie.201400560

  日期：2014.9.15

  Direct, oxidative metal‐catalyzed CH functionalizations of arenes are important in synthetic organic chemistry. Often, (over‐)stoichoimetric amounts of organic or inorganic oxidants have to be used in these reactions. The combination of rhodium and photoredox catalysis with visible light allows the direct CH olefination of arenes. Small amounts (1 mol %) of a photoredox catalyst resulted in the efficient

  芳烃的直接，氧化金属催化的CH官能化在合成有机化学中很重要。通常，在这些反应中必须使用（化学计量）过量的有机或无机氧化剂。铑和光氧化还原催化与可见光的结合可以使芳烃直接进行CH烯化反应。少量（1摩尔％）的光氧化还原催化剂可在温和的条件下有效地对多种底物进行有效的CH功能化。
• Complete Switch of Selectivity in the C–H Alkenylation and Hydroarylation Catalyzed by Iridium: The Role of Directing Groups
  作者：Jiyu Kim、Sung-Woo Park、Mu-Hyun Baik、Sukbok Chang

  DOI：10.1021/jacs.5b09824

  日期：2015.10.28

  A complete switch in the Cp*Ir(III)-catalyzed paths between C-H olefination and hydroarylation was found to be crucially dependent on the type of directing groups. This dichotomy in product distribution was correlated to the efficiency in attaining syn-coplanarity of olefin-inserted 7-membered iridacycles. Theoretical studies support our hypothesis that the degree of flexibility of this key intermediate modulates the beta-H elimination, which ultimately affords the observed chemoselectivity.