ethyl (Z)-2-fluoro-5-phenylpent-2-enoate | 211614-09-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (Z)-2-fluoro-5-phenylpent-2-enoate
• 英文别名: (Z)-ethyl 2-fluoro-5-phenylpent-2-enoate
• CAS: 211614-09-4
• 化学式: C₁₃H₁₅FO₂
• 分子量: 222.259
• InChiKey: LDGOMYAIJKOHEJ-BENRWUELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  6
• 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：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (Z)-2-fluoro-5-phenylpent-2-enoate 在 水 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以97%的产率得到(Z)-2-fluoro-5-phenylpent-2-enoic acid
  参考文献：
  名称：

  Pd和Cu催化的立体和区域控制的脱羧/ C ？杂芳烃的H氟烯基化

  摘要：

  报道了杂芳烃与α-氟丙烯酸的Pd / Cu催化的脱羧/直接CH烯基化反应。该方法可经济，立体地控制宝贵的杂芳基单氟烯烃（Z和E异构体），已知可用于合成氟化生物分子。

  DOI：

  10.1002/chem.201405119
• 作为产物：
  描述：

  triethyl 2-fluoro-3-oxo-5-phenyl-2-phosphonopentanoate 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以76%的产率得到ethyl (Z)-2-fluoro-5-phenylpent-2-enoate
  参考文献：
  名称：

  Tandem reduction–olefination for the stereoselective synthesis of (Z)-α-fluoro-α,β-unsaturated esters

  摘要：

  A tandem stereoselective reduction-olefination reaction of ethyl 2-acyl-2-fluoro-2-diethylphosphonoacetate employing NaBH4 in EtOH was developed. The one-pot reaction gave alpha-fluoro-alpha,beta-unsaturated esters with excellent (Z)-selectivity. A plausible mechanism involving a diastereoselective reduction predicted by the Felkin-Anh model, followed by olefination similar to the Horner-Wadsworth-Emmons reaction, has been proposed. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00778-0

文献信息

• Stereoselective formation of (Z)-2-fluoroalkenoates via Julia–Kocienski reaction of aldehydes with pyrimidinyl-fluorosulfones
  作者：Florent Larnaud、Emmanuel Pfund、Bruno Linclau、Thierry Lequeux

  DOI：10.1016/j.tet.2014.06.081

  日期：2014.9

  This sulfone allowed the preparation of Z-fluoroalkenoates with very high stereoselectivity from both aromatic and aliphatic aldehydes. The nature of the heterocycle on the course of the Julia–Kocienski reaction is discussed.

  从嘧啶基氟砜报道了氟代链烯酸酯的选择性合成。该砜允许由芳族和脂族醛两者制备具有非常高的立体选择性的Z-氟代链烯酸酯。讨论了Julia-Kocienski反应过程中杂环的性质。
• A Facile and Mild Approach for Stereoselective Synthesis of α-Fluoro-α,β-unsaturated Esters from α-Fluoro-β-keto Esters via Deacylation
  作者：Wenbin Yi、Jinlong Qian、Meifang Lv、Chun Cai

  DOI：10.1055/s-0034-1378917

  日期：——

  The highly stereoselective olefination reaction of α-fluoro-β-keto esters for the synthesis of α-fluoro-α,β-unsaturated esters has been developed. The olefination combines nucleophilic addition, intramolecular nucleophilic addition, and elimination in one step, as well as provides a facile synthetic approach to α-fluoro-α,β-unsaturated esters which are important units in many biologically active compounds

  α-氟-β-酮酯的高度立体选择性烯化反应用于合成α-氟-α,β-不饱和酯已经被开发出来。烯化在一个步骤中结合了亲核加成、分子内亲核加成和消除，并为α-氟-α,β-不饱和酯提供了一种简便的合成方法，α-氟-α,β-不饱和酯是许多生物活性化合物中的重要单元和各种有用的前体功能组转换。
• New Reaction Mode of the Horner-Wadsworth-Emmons Reaction for the Preparation of α-Fluoro-α,β-unsaturated Esters
  作者：Shigeki Sano、Tsuyoshi Ando、Kenji Yokoyama、Yoshimitsu Nagao

  DOI：10.1055/s-1998-1780

  日期：1998.7

  E-selectivity was observed in the Horner-Wadsworth-Emmons (HWE) reactions of ethyl 2-fluoro-2-diethylphosphonoacetate 1 with alkyl aryl ketones 2a-f using Sn(OSO2CF3)2 and N-ethylpiperidine. Mg(II)-promoted HWE reactions of 1 with aldehydes 2h,i afforded α-fluoro-α,β-unsaturated esters 3h,i in a Z-selective manner depending on the reaction temperatures.

  在使用 Sn(OSO2CF3)2 和 N-乙基哌啶的 2-氟-2-二乙基膦酰基乙酸乙酯 1 与烷基芳基酮 2a-f 的 Horner-Wadsworth-Emmons (HWE) 反应中观察到了优异的 E 选择性。Mg(II) 促进的 1 与醛 2h,i 的 HWE 反应根据反应温度以 Z 选择性方式提供了 α-氟-α,β-不饱和酯 3h,i。
• <i>Z</i>-Selective or Stereospecific Alkenylation Reaction: A Novel Synthetic Method for α-Fluoro-α,β-unsaturated Esters
  作者：Mitsuhiro Yoshimatsu、Yoshinori Murase、Akinori Itoh、Genzoh Tanabe、Osamu Muraoka

  DOI：10.1246/cl.2005.998

  日期：2005.7

  The Z-selective formation of α-fluoro-α,β-unsaturated esters was achieved using the deselenenic acid of the syn- and/or anti-3-aryl-2-fluoro-3-hydroxy-2-organoselanylacetates 3 and 4 with trifluoro...

  使用顺-和/或反-3-芳基-2-氟-3-羟基-2-有机硒基乙酸酯3和4的脱硒酸实现α-氟-α,β-不饱和酯的Z-选择性形成三氟...
• Efficient Synthesis of Fluoroalkenes via Diethylzinc-Promoted Wittig Reaction
  作者：Philippe Jubault、Xavier Pannecoucke、Ludivine Zoute、Guillaume Dutheuil、Jean-Charles Quirion

  DOI：10.1055/s-2006-950208

  日期：2006.10

  The synthesis of α-fluoroacrylates and α-bromo-α-fluoroalkenes was achieved in very good yields using aldehydes and ketones, triphenylphosphine, diethylzinc as promoter, and ethyl dibromofluoroacetate or dibromofluoromethane, respectively. A change in the addition sequence was critical in order to obtain exclusively α-fluoroacrylates in good yields.

  α-氟丙烯酸酯和α-溴-α-氟烯烃的合成得到了非常好的产率，使用了醛和酮、三苯基磷、二乙基锌作为促进剂，以及乙基二溴氟乙酸酯或二溴氟甲烷。改变添加顺序对独占性获得α-氟丙烯酸酯的高产率至关重要。