ethyl (E)-4-phenyl-3-pentenoate | 87567-66-6

• 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: ethyl (E)-4-phenyl-3-pentenoate
• 英文别名: 4-phenyl-pent-3-enoic acid ethyl ester；4-Phenyl-pent-3-ensaeure-aethylester；ethyl (E)-4-phenylpent-3-enoate
• CAS: 87567-66-6
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: BCBPRQKFRTUBSE-PKNBQFBNSA-N

物化性质

• 沸点：
  299.1±20.0 °C(predicted)
• 密度：
  1.004±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl (E)-4-phenyl-3-pentenoate 在 dirhodium tetraacetate 、 4-乙酰氨基苯磺酰叠氮 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 (E)-2-(Dimethyl-phenyl-silanyl)-4-phenyl-pent-3-enoic acid ethyl ester
  参考文献：
  名称：

  铑（II）-乙烯基类胡萝卜素插入SiH键中。烯丙基硅烷的立体定向合成的新方法

  摘要：

  在有机硅烷的存在下，Rh 2（OAc）4催化的乙烯基重氮羰基化合物的分解立体定向地以良好的收率生成了相应的烯丙基硅烷。还考虑了不对称方法，以及将方法扩展到其他烯丙基系统的合成。

  DOI：

  10.1016/0040-4039(94)88508-7
• 作为产物：
  描述：

  丙烯醛缩二乙醇 在 正丁基锂 、 双氧水 、 对甲苯磺酸 作用下， 以 乙醇 、 正己烷 为溶剂， 反应 63.17h， 生成 ethyl (E)-4-phenyl-3-pentenoate
  参考文献：
  名称：

  Stereoselective Syntheses of β,γ-Unsaturated Esters and γ-Lactones:  1-(Benzotriazol-1-yl)-3-(diphenylphosphoryl)-1-ethoxy-1-propene, a Protected CCH₂CO₂Et Synthon Equivalent

  摘要：

  1-(Benzotriazol-1-yl)-3-(diphenylphosphoryl)-1-ethoxy-1-propene (3), prepared from N-(alpha-ethoxy-allyl)benzotriazole (1), underwent selective Horner reactions with aldehydes to give substituted dienes. Subsequent hydrolysis of these intermediates readily produced beta,gamma-unsaturated esters 2a-c in good yields. Similar reactions with ketones followed by hydrolysis of 10 produced, depending on the conditions, either the corresponding gamma,gamma-disubstituted beta,gamma-unsaturated esters 11a-d or gamma-lactones 9a-c and 13. A double lithiation process provided beta,gamma,gamma-trisubstituted beta,gamma-unsaturated esters 15, 18, and beta,gamma,gamma-trisubstituted gamma-lactone 14.

  DOI：

  10.1021/jo9701647

文献信息

• Palladium-catalyzed addition of organoboronic acids to allenes
  作者：Chang Ho Oh、Tae Won Ahn、Raghava Reddy V.

  DOI：10.1039/b309258e

  日期：——

  The palladium-catalyzed addition reaction of alkenyl- or aryl-boronic acids into various allenes is described, which allows C-C bond formation in a highly regioselective manner under very mild conditions.

  描述了链烯基-或芳基-硼酸在钯催化下的加成反应，形成各种烯基，这使得在非常温和的条件下以高度区域选择性的方式形成CC键。
• Radical Alkenylation of α-Halo Carbonyl Compounds with Alkenylindiums
  作者：Kazuaki Takami、Hideki Yorimitsu、Koichiro Oshima

  DOI：10.1021/ol048070o

  日期：2004.11.1

  Alkenylation reaction of alpha-halo carbonyl compounds with alkenylindiums proceeded via a radical process in the presence of triethylborane. Unactivated alkene moieties as well as a styryl group could be introduced by this method. The geometry of the carbon-carbon double bonds of the alkenylindiums was retained. Preparation of an alkenylindium via a hydroinclation of 1-alkyne followed by radical alkenylation established an efficient one-pot strategy.
• A Stereospecific Access to Allylic Systems Using Rhodium(II)−Vinyl Carbenoid Insertion into Si−H, O−H, and N−H Bonds
  作者：Priyadarshanie Bulugahapitiya、Yannick Landais、Liliana Parra-Rapado、Denis Planchenault、Valéry Weber

  DOI：10.1021/jo961952j

  日期：1997.3.1

  Rhodium-catalyzed decomposition of alpha-vinyldiazoesters in the presence of silanes, alcohols, ethers, amines, and thiols have been shown to produce the corresponding alpha-silyl, alpha-hydroxy, alpha-alkoxy, alpha-amino, and alpha-thioalkoxy esters in generally good yield with a complete retention of the stereochemistry of the double bond of the diazo precursor. An extension of the process in homochiral series has also been devised using either a chiral auxiliary attached to the ester function or achiral alpha-vinyldiazoesters and Doyle's chiral catalyst Rh-2(MEPY)(4). In the former approach, pantolactone as chiral auxiliary gave diastereoselectivities of up to 70%, while the second approach produced the desired allylsilane with ee as high as 72%. On the other hand, Rh-2(MEPY)(4)-catalyzed insertion into the O-H bond of water led to poor or no enantioselectivity in good agreement with recent literature reports.
• ——
  作者：N. N. Romanova、A. G. Gravis、P. V. Kudan、I. F. Leshcheva、N. V. Zyk

  DOI：10.1023/a:1026065414176

  日期：——

  The reactions of 2-phenylpropanal with ethyl hydrogen malonate and benzylamine (or benzylammonium acetate) and of ethyl 4-phenyl-2-pentenoate with benzylamine take different pathways, depending on the conditions.
• Rhodium(II)-vinylcarbenoid insertion into the SiH bond. A new stereospecific synthesis of allylsilanes
  作者：Yannick Landais、Denis Planchenault、Valéry Weber

  DOI：10.1016/0040-4039(94)88508-7

  日期：1994.12

  catalysed decomposition of vinyldiazocarbonyl compounds in the presence of organosilanes led stereospecifically to the corresponding allylsilanes in good yields. An asymmetric approach has also been considered as well as the extension of the methodology to the synthesis of other allylic systems.

  在有机硅烷的存在下，Rh 2（OAc）4催化的乙烯基重氮羰基化合物的分解立体定向地以良好的收率生成了相应的烯丙基硅烷。还考虑了不对称方法，以及将方法扩展到其他烯丙基系统的合成。