ethyl (E)-5-(4-chlorophenyl)pent-4-enoate | 38379-83-8

• 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)-5-(4-chlorophenyl)pent-4-enoate
• 英文别名: 1t-(4-chloro-phenyl)-penten-(1)-oic acid-(5)-ethyl ester；1t-(4-Chlor-phenyl)-penten-(1)-saeure-(5)-aethylester
• CAS: 38379-83-8
• 化学式: C₁₃H₁₅ClO₂
• 分子量: 238.714
• InChiKey: XYVXPIMKVZQLDQ-HWKANZROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 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：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  ethyl (E)-5-(4-chlorophenyl)pent-4-enoate 生成 (E)-5-(4-chlorophenyl)pent-4-enoic acid
  参考文献：
  名称：

  Reagent‐Controlled Asymmetric Iodolactonization Using Cinchona Alkaloids as Chiral Sources

  摘要：

  A novel method for reagent-controlled asymmetric iodolactonization of 5-aryl-4-pentenoic acids is reported. This work uses carboxylate ion pairs combined with cinchona alkaloids as chiral sources of carboxylate anion for the first time leading to a mixture of two regio-isomeric iodolactones with moderate enantioselectivity (exo- 18.5% ee, endo-35.0% ee) under mild reaction conditions.

  DOI：

  10.1081/scc-120028633
• 作为产物：
  描述：

  原乙酸三乙酯 、 生成 ethyl (E)-5-(4-chlorophenyl)pent-4-enoate
  参考文献：
  名称：

  Reagent‐Controlled Asymmetric Iodolactonization Using Cinchona Alkaloids as Chiral Sources

  摘要：

  A novel method for reagent-controlled asymmetric iodolactonization of 5-aryl-4-pentenoic acids is reported. This work uses carboxylate ion pairs combined with cinchona alkaloids as chiral sources of carboxylate anion for the first time leading to a mixture of two regio-isomeric iodolactones with moderate enantioselectivity (exo- 18.5% ee, endo-35.0% ee) under mild reaction conditions.

  DOI：

  10.1081/scc-120028633

文献信息

• Lewis Base Catalyzed, Sulfenium Ion Initiated Enantioselective, Spiroketalization Cascade
  作者：Kimberly M. Hilby、Scott E. Denmark

  DOI：10.1021/acs.joc.1c02271

  日期：2021.11.5

  A Lewis base catalyzed, enantioselective sulfenocyclization of alkenes to afford [6,6]spiroketals has been developed. The method uses a chiral Lewis base catalyst with an electrophilic sulfur source to generate enantioenriched thiiranium ion with alkenes. Upon formation, the thiiranium ion is subsequently captured in a cascade-type reaction, wherein a ketone oxygen serves as the nucleophile to open

  已经开发了一种路易斯碱催化的烯烃对映选择性磺基环化以提供 [6,6] 螺缩酮。该方法使用具有亲电子硫源的手性路易斯碱催化剂与烯烃生成对映体富集的硫鎓离子。形成后，硫鎓离子随后在级联反应中被捕获，其中酮氧作为亲核试剂打开硫鎓离子，醇提供二次环化以形成生物相关的螺缩酮。各种富电子和电子中性E-取代的苯乙烯以良好的产率形成所需的螺缩酮，具有优异的对映选择性和非对映选择性。烷基取代和末端烯烃参与级联反应，但与苯乙烯基底物相比范围有限。该方法允许以良好的收率和优异的对映选择性快速形成高度取代的螺缩酮。
• Rhodium-catalyzed asymmetric hydroboration of γ,δ-unsaturated amide derivatives: δ-borylated amides
  作者：G. L. Hoang、S. Zhang、J. M. Takacs

  DOI：10.1039/c8cc01563e

  日期：——

  γ,δ-Unsaturated amides in which the alkene moiety bears an aryl or heteroaryl substituent undergo regioselective rhodium-catalyzed δ-borylation by pinacolborane to afford chiral secondary benzylic boronic esters. The results contrast the γ-borylation of γ,δ-unsaturated amides in which the disubstituted alkene moiety bears only alkyl substituents; the reversal in regiochemistry is coupled with a reversal

  γ，δ-不饱和酰胺（其中烯基部分带有芳基或杂芳基取代基）通过频哪醇硼烷进行区域选择性铑催化的δ-硼化，从而获得手性仲苄基硼酸酯。结果对比了γ，δ-不饱和酰胺的γ-硼化，其中双取代的烯烃部分仅带有烷基取代基。区域化学的逆转与π-面部选择性意义上的逆转相结合。
• Reformatsky Condensations Involving Vinylogs of Haloacetic Esters
  作者：Reynold C. Fuson、R. T. Arnold、H. G. Cooke

  DOI：10.1021/ja01276a068

  日期：1938.9