(E)-ethyl 2-fluoro-3-(4-methoxyphenyl)-2-propenoate | 26927-87-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-ethyl 2-fluoro-3-(4-methoxyphenyl)-2-propenoate
• 英文别名: ethyl (E)-2-fluoro-3-(4-methoxyphenyl)propenoate；(E)-ethyl 2-fluoro-3-(4-methoxyphenyl)acrylate；ethyl (E)-2-fluoro-3-(4-methoxyphenyl)acrylate；cis-α-Fluor-4-methoxy-zimtsaeureethylester；(E)-2-Fluoro-3-(4-methoxyphenyl)-propenoic acid, ethyl ester；ethyl (E)-2-fluoro-3-(4-methoxyphenyl)prop-2-enoate
• CAS: 26927-87-7
• 化学式: C₁₂H₁₃FO₃
• 分子量: 224.232
• InChiKey: HAVOABSXFULZTO-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 2-fluoro-3-(4-methoxyphenyl)-2-propenoate 在 水 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以57%的产率得到(E)-2-fluoro-3-(4-methoxyphenyl)acrylic 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：

  2-氟-2-磷酰基乙酸三乙酯 、 4-甲氧基苯甲醛 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以62%的产率得到(E)-ethyl 2-fluoro-3-(4-methoxyphenyl)-2-propenoate
  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

文献信息

• The One-Pot Wittig Reaction: A Facile Synthesis of α,β-Unsaturated Esters and Nitriles by Using Nanocrystalline Magnesium Oxide
  作者：Boyapati M. Choudary、Koosam Mahendar、M. Lakshmi Kantam、Kalluri V. S. Ranganath、Taimur Athar

  DOI：10.1002/adsc.200606001

  日期：2006.9

  Nanocrystalline magnesium oxide was found to be an effective heterogeneous, solid base catalyst for the one-pot Wittig reaction to afford α,β-unsaturated esters and nitriles in excellent yields with high E-stereoselectivity in the presence of triphenylphosphine under mild conditions.

  发现纳米晶氧化镁是一种有效的非均相，固态碱催化剂，可在一锅Wittig反应中以温和条件在三苯基膦存在下以高收率和高E-立体选择性以优异的产率提供α，β-不饱和酯和腈。
• 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。
• 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。
• Highly regioselective SN2′ reaction of β-fluoroallylic phosphates with organocopper reagents and its application to the synthesis of fluorine-containing carbocycles
  作者：Takashi Nihei、Yusuke Kubo、Takashi Ishihara、Tsutomu Konno

  DOI：10.1016/j.jfluchem.2014.06.012

  日期：2014.11

  Treatment of beta-fluoroallyl phosphates with 2.2 equiv. of organocuprates, prepared readily from 2.2 equiv. each of CuCN and organometallics (organolithium reagents, Grignard reagents, and organozinc reagents), in THF at -40 to 0 degrees C for 0.25 to 24 h gave gamma-products in a highly regioselective manner. Thus obtained gamma-adducts were subjected to the ring-closing metathesis, the corresponding cyclic fluoroalkenes being afforded in good yields. (C) 2014 Elsevier B.V. All rights reserved.
• Enantioselective bioreduction of 2-fluoro-2-alken-1-ols mediated by Saccharomyces cerevisiae
  作者：Fan Luo、Dengfu Lu、Yuefa Gong

  DOI：10.1016/j.molcatb.2011.02.011

  日期：2011.7

  Biocatalytic reduction of 2-fluoro-2-alken-1-ols mediated by Saccharomyces cerevisiae underwent smoothly and yielded (S)-2-fluorinated alkanols with high enantioselectivities. The conversion rate was markedly depending on the configuration of alkene moiety of the substrate, the chain length of alkyl group at beta position of C=C bond, as well as the reaction conditions. (C) 2011 Elsevier B.V. All rights reserved.