methyl (E)-3-(2-benzoylphenyl)acrylate | 1373824-12-4

• 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: methyl (E)-3-(2-benzoylphenyl)acrylate
• 英文别名: methyl (E)-3-(2′-benzoylphenyl)acrylate；methyl trans-3-(2-benzoylphenyl)-2-propenoate；Methyl trans-3-(2-benzoylphenyl)propenoate；methyl (E)-3-(2-benzoylphenyl)prop-2-enoate
• CAS: 1373824-12-4
• 化学式: C₁₇H₁₄O₃
• 分子量: 266.296
• InChiKey: HPYWZDLGTYQIPC-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (E)-3-(2-benzoylphenyl)acrylate 在 肼 作用下， 以 水 、 乙二醇 为溶剂， 反应 0.5h， 以20%的产率得到
  参考文献：
  名称：

  Dual Role of Acetanilides: Traceless Removal of a Directing Group through Deacetylation/Diazotation and Palladium-Catalyzed C–C-Coupling Reactions

  摘要：

  The acetamide group enables regioselective oxidative ortho-C-H activation reactions, such as Pd-catalyzed acylation. The synthetic utility of these transformations can be significantly enhanced by using the acetamide as a quasi-leaving group in a subsequent conventional Pd-catalyzed coupling or cross-coupling reaction. The concept is illustrated herein for the synthesis of o-alkenyl- and o-arylphenones, which have potential for the synthesis of arylated aromatic heterocycles.

  DOI：

  10.1021/acs.joc.5b00272
• 作为产物：
  描述：

  N-乙酰苯胺 在 叔丁基过氧化氢 、 三氟化硼甲醇络合物 、 palladium diacetate 、 sodium dodecyl sulfate 、 三氟乙酸 作用下， 以 甲醇 、 水 为溶剂， 反应 54.0h， 生成 methyl (E)-3-(2-benzoylphenyl)acrylate
  参考文献：
  名称：

  Dual Role of Acetanilides: Traceless Removal of a Directing Group through Deacetylation/Diazotation and Palladium-Catalyzed C–C-Coupling Reactions

  摘要：

  The acetamide group enables regioselective oxidative ortho-C-H activation reactions, such as Pd-catalyzed acylation. The synthetic utility of these transformations can be significantly enhanced by using the acetamide as a quasi-leaving group in a subsequent conventional Pd-catalyzed coupling or cross-coupling reaction. The concept is illustrated herein for the synthesis of o-alkenyl- and o-arylphenones, which have potential for the synthesis of arylated aromatic heterocycles.

  DOI：

  10.1021/acs.joc.5b00272

文献信息

• Multibond Forming Tandem Reactions of Anilines via Stable Aryl Diazonium Salts: One-Pot Synthesis of 3,4-Dihydroquinolin-2-ones
  作者：Réka J. Faggyas、Megan Grace、Lewis Williams、Andrew Sutherland

  DOI：10.1021/acs.joc.8b01910

  日期：2018.10.19

  A fast and effective one-pot tandem process that generates Heck coupled products from readily available anilines via stable aryl diazonium tosylate salts was developed. The mild and simple procedure involves rapid formation of aryl diazonium salts using a polymer-supported nitrite reagent and p-tosic acid, followed by a base-free Heck–Matsuda coupling with acrylates and styrenes. Using 2-nitroanilines

  开发了一种快速有效的一锅串联方法，该方法可通过稳定的芳基重氮甲苯磺酸盐从易于获得的苯胺生成Heck偶联产物。温和而简单的步骤涉及使用聚合物负载的亚硝酸盐试剂和对羟基苯甲酸酯快速形成芳基重氮盐-甲苯磺酸，然后与丙烯酸酯和苯乙烯进行无碱Heck-Matsuda偶联。使用2-硝基苯胺作为底物，将一锅串联方法扩展到直接合成3,4-二氢喹啉-2-酮。在这种情况下，经过重氮化和Heck-Matsuda偶联生成肉桂酸甲酯，添加氢气并再利用钯催化剂还原硝基和烯烃氢化，可有效形成3,4-二氢喹啉-2-酮。 。一锅四步法的合成效用通过基于喹啉酮的钠离子通道调节剂的五锅法合成得到了证明。
• Heck-type reaction of aryldiazonium silica sulfates
  作者：Azadeh Pirisedigh、Amin Zarei、Hojjat Seyedjamali、Leila Khazdooz、Abdol R. Hajipour

  DOI：10.1007/s00706-011-0632-1

  日期：2012.5

  Aryldiazonium silica sulfates were employed as new and efficient reagents for Heck-type arylation reactions with styrene and methyl acrylate. The reactions were carried out in an organic solvent, in the presence of Pd(OAc)(2) as precatalyst without use of base and free ligand. The trans isomers of desired products, methyl cinnamates and stilbenes, were obtained with full conversion. Use of a catalytic amount of Pd(OAc)(2) produced the corresponding products in short reaction times and excellent yields.
• ENDOTHELIN RECEPTOR ANTAGONISTS
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP0723449A1

  公开（公告）日：1996-07-31
• EP0723449A4
  申请人：——

  公开号：EP0723449A4

  公开（公告）日：1996-09-11
• US5817653A
  申请人：——

  公开号：US5817653A

  公开（公告）日：1998-10-06