(E)-methyl 2,4-diphenylbut-3-enoate | 101596-62-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-methyl 2,4-diphenylbut-3-enoate
• 英文别名: methyl (E)-2,4-diphenylbut-3-enoate
• CAS: 101596-62-7
• 化学式: C₁₇H₁₆O₂
• 分子量: 252.313
• InChiKey: WNHJHUMBHUKPRP-OUKQBFOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (E)-methyl 2,4-diphenylbut-3-enoate 在 lithium aluminium tetrahydride 作用下， 生成 (E)-2,4-diphenylbut-3-en-1-ol
  参考文献：
  名称：

  1,3-Diphenyl-1,3-butadiene Dimers¹

  摘要：

  DOI：

  10.1021/jo01105a018
• 作为产物：
  描述：

  苯乙酸甲酯 在 对甲苯磺酰叠氮 、 三(五氟苯基)硼烷 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 12.0h， 生成 (E)-methyl 2,4-diphenylbut-3-enoate
  参考文献：
  名称：

  硼催化烯丙醇的CC功能化

  摘要：

  本文介绍了使用供体-受体碳烯的三（五氟苯基）硼烷催化的芳基烯丙醇的C-C键功能化。发现烯丙基羟基通过邻近基团的参与来协助产物形成，从而提供了对机械理解的线索。该方法也可用于使烯丙醇同化为烯丙基醇。总的来说，这种无金属的转变为碳-碳键的断裂和形成提供了一种新颖的分离策略。

  DOI：

  10.1002/adsc.201801389

文献信息

• Ruthenium-Catalyzed Chemo-Selective Carbene Insertion into C–H Bond of Styrene over Cyclopropanation: C–C Bond Formation
  作者：Arumugam Jayarani、Masilamani Deepa、Hilal Ahmad Khan、Fathima Febin Koothradan、Sekar Yoganandhini、Vinod Sreelakshmi、Chinnappan Sivasankar

  DOI：10.1021/acs.joc.3c01881

  日期：2023.11.17

  synthesis. Heck reaction is known to arylate the terminal carbon of olefins; however, direct alkylation of the terminal carbon of olefin is limited. Herein, we report a novel ruthenium-catalyzed selective cross-coupling reaction of styrene and α-diazoesters to form a new C–C bond over cyclopropanation via the C–H insertion process for the first time. Using this novel methodology, a wide variety of substrates

  C-C键形成反应在有机合成中很重要。已知 Heck 反应可使烯烃末端碳芳基化；然而，烯烃末端碳的直接烷基化受到限制。在此，我们首次报告了一种新型的钌催化苯乙烯和α-重氮酯的选择性交叉偶联反应，通过C-H插入过程在环丙烷化过程中形成新的C-C键。利用这种新颖的方法，可以利用多种底物，并在温和的反应条件下合成出具有良好立体选择性的各种α-乙烯基化苄酯和密集官能化的烯烃。整个反应过程通过卡宾插入苯乙烯中进行，以良好至优异的产率和适当的立体选择性形成所需的产物。选择性C-H插入产物、宽底物范围和优异的官能团耐受性是本工作的最佳特点。
• ——
  作者：Shuangying Liu、Jürgen F. K. Müller、Markus Neuburger、Silvia Schaffner、Margareta Zehnder

  DOI：10.1002/1522-2675(20000607)83:6<1256::aid-hlca1256>3.0.co;2-5

  日期：2000.6.7

  The novel chiral P,N-ligand 2-[2-(diphenylphosphino)phenyl]-5,6-dihydro-4-phenyl-4H-1,3-oxazine (4) was synthesized. The corresponding dihydro[(phosphino-xP)aryl]oxazine-xN} (eta(3)-diphenylallyl)palladium(II) hexafluorophosphate 5 and the analogous [Pd(eta(3)-1,3-dimethylallyl)] complex 6 were investigated by X-ray analysis and 1D- and 2D-NMR spectroscopy. The complex 5 exists as 'exo'-syn-syn isomer in the solid state (Fig. 1). In solution, the same isomer exceeds with 90%. The X-ray crystal structure of 6 reveals that the dihydro(phosphinoaryl)oxazine ligand coordinates in a pseudo-enantiomeric conformation compared with that of 5 (Fig. 3). A syn-anti arrangement of the allyl substituents of 6 is favored in the solid state. H-1-NMR Spectroscopic investigations suggest that the auxiliary 6 adopts two conformations. This conformational instability together with 'exo'/'endo' and syn/anti isomerization leads to the formation of 6 isomers (Fig. 4). The asymmetric allylic substitution reaction of 1,3-diphenylallyl acetate with dimethyl malonate in the presence of 4 proceeds with a selectivity of 99% ee. The ee induced by 4 in the catalytic allylic substitution BE 1-methylbut-2-enyl acetate is moderate (54%).
• Enantiomerically pure 1-(2-methoxy-1-naphthyl) and 1-(2-methylthio-1-naphthyl)isoquinoline: two new axially chiral NO and NS ligands for asymmetric catalysis
  作者：Giorgio Chelucci、Alessia Bacchi、Davide Fabbri、Antonio Saba、Fausta Ulgheri

  DOI：10.1016/s0040-4039(98)02353-3

  日期：1999.1

  The synthesis and resolution of 1-(2-methoxy-1-naphthyl)isoquinoline and 1-(2-methylthio-1-naphthyl)isoquinoline is reported. These ligands were assessed in the enantioselective palladium catalyzed allylic substitution of 1,3-diphenylprop-2-enyl acetate with dimethylmalonate. Enantioselectivity up to 68% was obtained. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
• Chiral Nonracemic Pyridine Thiols and Thioethers Applied in Palladium-Catalyzed Allylic Substitution. An Example of Near-Perfect Enantioselection
  作者：B. Koning、A. Meetsma、R. M. Kellogg

  DOI：10.1021/jo9806299

  日期：1998.8.1

  Pyridine thiols and dithiols have been synthesized by base-induced addition of 2,6-lutidine to thiofenchone. These thiols were converted to their thioether derivatives by alkylation. Application of these compounds in palladium-catalyzed allylic substitution on 1,3-diphenylprop-2-enyl acetate gave nearly absolute enantiomeric excess (98%) and high chemical yield (96%). Isolation of a palladium allylic intermediate gave insight in the origin of chiral recognition for these systems.