ethyl (E)-3,4-diphenyl-3-butenoate | 130240-34-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: ethyl (E)-3,4-diphenyl-3-butenoate
• 英文别名: ethyl (E)-3,4-diphenylbut-3-enoate；3,4-diphenyl-but-3-enoic acid ethyl ester；3,4-Diphenyl-but-3-ensaeure-aethylester
• CAS: 130240-34-5
• 化学式: C₁₈H₁₈O₂
• 分子量: 266.34
• InChiKey: KOCGHIBMZXHPNK-GHRIWEEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  ethyl (E)-3,4-diphenyl-3-butenoate 在 sodium hydroxide 作用下， 生成 3,4-diphenyl-but-3-enoic acid
  参考文献：
  名称：

  Phalnikar; Nargund, Journal of the University of Bombay, Science: Physical Sciences, Mathematics, Biological Sciences and Medicine, 1939, vol. 8/, p. 184,187

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 乙酸酐 作用下， 生成 ethyl (E)-3,4-diphenyl-3-butenoate
  参考文献：
  名称：

  291. 2-苯基萘的合成

  摘要：

  DOI：

  10.1039/jr9340001332

文献信息

• Regio- and Stereoselective Nickel-Catalyzed Coupling of Boronic Acids with Allenoates
  作者：Marco Bandini、Yang Liu、Mario Daka

  DOI：10.1055/s-0037-1610023

  日期：2018.8

  The Ni(II)-catalyzed cross-coupling of arylboronic acids with allenoates is documented. The high regio- and stereoselectivity of the process enables a wide range of β-aryl β,γ-unsaturated esters to be prepared in good to excellent yields (up to 95%) and high E/Z-selectivity. Additionally, [3+2]-cascade sequence was observed when 2-formylphenylboronic acid was employed. The Ni(II)-catalyzed cross-coupling

  作为专题“现代耦合方法及其在综合中的战略应用”的一部分发布 抽象的 Ni（II）催化的芳基硼酸与脲基甲酸酯的交叉偶联。该方法的高区域选择性和立体选择性使得能够以高至优异的产率（高达95％）和高的E / Z选择性来制备各种各样的β-芳基β，γ-不饱和酯。另外，当使用2-甲酰基苯基硼酸时，观察到[3 + 2]级联序列。 Ni（II）催化的芳基硼酸与脲基甲酸酯的交叉偶联。该方法的高区域选择性和立体选择性使得能够以高至优异的产率（高达95％）和高的E / Z选择性来制备各种各样的β-芳基β，γ-不饱和酯。另外，当使用2-甲酰基苯基硼酸时，观察到[3 + 2]级联序列。
• Copper-catalyzed 1,1-arylalkylation of terminal alkynes with diazo esters and organoboronic acids
  作者：Yunhe Lv、Weiya Pu、Xueru Liu、Jinye Sun、Mengxing Cui

  DOI：10.1039/c9cc07461a

  日期：——

  A novel copper-catalyzed 1,1-arylalkylation of terminal alkynes with diazo esters and organoboronic acids is described. With this methodology, (E)-β-aryl-β,γ-unsaturated esters can be easily constructed in good to excellent yields directly from readily available and inexpensive traditional coupling reagents.

  描述了一种新型的铜催化的末端炔烃与重氮酯和有机硼酸的1,1-芳基烷基化反应。利用这种方法，可以直接从容易获得和廉价的传统偶联剂中容易地以高至优异的产率构建（E）-β-芳基-β，γ-不饱和酯。
• Reactions of Arylazoxy Aryl Sulfones with α,β-Unsaturated Esters and Nitriles in the Presence of a Palladium(0) Catalyst
  作者：Nobumasa Kamigata、Mayumi Satoh、Takamasa Fukushima

  DOI：10.1246/bcsj.63.2118

  日期：1990.7

  The reactions of arylazoxy aryl sulfones (1) with α,β-unsaturated esters and nitriles in the presence of a palladium(0) catalyst were found to give aryl-substituted esters and nitriles in good yield.

  发现芳基偶氮芳基砜 (1) 与 α,β-不饱和酯和腈在钯 (0) 催化剂存在下的反应以良好的收率得到芳基取代的酯和腈。
• Bergmann; Hoffmann; Meyer, Journal fur praktische Chemie (Leipzig 1954), 1932, vol. <2> 135, p. 245,252
  作者：Bergmann、Hoffmann、Meyer

  DOI：——

  日期：——
• Structure-activity studies on benzhydrol-containing nipecotic acid and guvacine derivatives as potent, orally-active inhibitors of GABA uptake
  作者：Michael R. Pavia、Sandra J. Lobbestael、David Nugiel、Daniel R. Mayhugh、Vlad E. Gregor、Charles P. Taylor、Roy D. Schwarz、Laura Brahce、Mark G. Vartanian

  DOI：10.1021/jm00100a032

  日期：1992.10

  The introduction of lipophilic groups onto the ring nitrogen of nipecotic acid and guvacine, two known GABA uptake inhibitors, afforded potent, orally-active anticonvulsant drugs. A series of compounds is reported which explores the structure-activity relationships (SAR) in this series. Among the areas explored: side-chain SAR (aromatic-, heterocyclic-, and tricyclic-containing side chains) and modifications to the tetrahydropyridine ring. The benzhydrol ether-containing side chains afforded the most potent compounds with several exhibiting in vitro IC50 values for GABA uptake of <1 muM (including 5, Table 1; 37, 43, Table IV; and 44, Table V). Compound 44 was selected for extensive evaluation and subsequently progressed to Phase 1 clinical trials with severe adverse effects seen after single dose administration to humans.