ethyl (Z)-3-(2-fluorophenyl)acrylate | 89760-43-0

• 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: ethyl (Z)-3-(2-fluorophenyl)acrylate
• 英文别名: ethyl (Z)-3-(2-fluorophenyl)prop-2-enoate
• CAS: 89760-43-0
• 化学式: C₁₁H₁₁FO₂
• 分子量: 194.206
• InChiKey: YOIVHDQJCFLRRB-FPLPWBNLSA-N

物化性质

• 沸点：
  269.0±15.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 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)-3-(2-fluorophenyl)acrylate 在 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以77%的产率得到(Z)-3-(2-fluorophenyl)acrylic acid
  参考文献：
  名称：

  Substituent effects of cis-cinnamic acid analogues as plant growh inhibitors

  摘要：

  1-O-cis-Cinnamoyl-beta-D-glucopyranose is one of the most potent allelochemicals that has been isolated from Spiraea thunbergii Sieb by Hiradate et al. It derives its strong inhibitory activity from cis-cinnamic acid (cis-CA), which is crucial for phytotoxicity. By preparing and assaying a series of cis-CA analogues, it was previously found that the key features of cis-CA for lettuce root growth inhibition are a phenyl ring, cis-configuration of the alkene moiety, and carboxylic acid. On the basis of a structure-activity relationship study, the substituent effects on the aromatic ring of cis-CA were examined by systematic synthesis and the lettuce root growth inhibition assay of a series of cis-CA analogues having substituents on the aromatic ring. While ortho- and para-substituted analogues exhibited low potency in most cases, meta-substitution was not critical for potency, and analogues having a hydrophobic and sterically small substituent were more likely to be potent. Finally, several cis-CA analogues were found to be more potent root growth inhibitors than cis-CA. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2013.08.013
• 作为产物：
  描述：

  乙基3-(2-氟苯基)丙-2-炔酸酯 在 三丁基膦 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 以58.333%的产率得到
  参考文献：
  名称：

  Z-选择性膦在水的存在下促进 ynoates 和 propynic amides 的 1,4-还原

  摘要：

  在水存在下，膦介导的取代丙炔酸酯和酰胺的还原产生了具有高Z选择性的部分还原的 α,β-不饱和酯和酰胺。在某些情况下，产物的竞争性原位 Z对E异构化降低了分离的 α,β-不饱和羰基产物的Z对E比。反应时间和反应混合物中的磷化氢和水的量是通过防止或降低Z - 至E -产物异构化速率来控制选择性的关键实验因素。密切的反应监测可以隔离Z-具有高选择性的烯烃。计算结果表明，由于EP -羟基正膦中间体的立体选择性形成，反应可能是高度Z选择性的。

  DOI：

  10.1039/d1ob00909e

文献信息

• Rh(III)-Catalyzed Enaminone-Directed C–H Coupling with α-Diazo-α-phosphonoacetate for Reactivity Discovery: Fluoride-Mediated Dephosphonation for C–C Coupling Reactions
  作者：Chao Song、Chen Yang、Hua Zeng、Wenjing Zhang、Shan Guo、Jin Zhu

  DOI：10.1021/acs.orglett.8b01406

  日期：2018.7.6

  Rh(III)-catalyzed enaminone-directed C–H coupling with α-diazo-α-phosphonoacetate has been used for the identification of fluoride-mediated dephosphonation C–C coupling reactivity for the synthesis of 4-hydroxy-1-naphthoates. Intermolecular C–C coupling of α-phosphonoacetate and benzaldehyde for (E)-selective α,β-unsaturated ester synthesis has also been achieved.

  Rh（III）催化的与α-重氮-α-膦酰基乙酸酯结合的烯胺酮定向的C–H偶联已用于鉴定氟化物介导的膦酰基化的C–C偶联反应，用于合成4-羟基-1-萘甲酸酯。还实现了α-膦酰基乙酸酯和苯甲醛的分子间CC偶联，用于（E）-选择性α，β-不饱和酯的合成。
• Reactions of coordinated ligands
  作者：Roy P. Houghton、Martyn Voyle、Raymond Price

  DOI：10.1016/0022-328x(83)87162-9

  日期：1983.12

  treated with potassium t-butoxide in dimethyl sulphoxide the chromium tricarbonyl complex of 3-(2-fluorophenyl)propan-1-ol underwent a rapid intramolecular nucleophilic substitution to give the corresponding complex of chroman, from which the heterocycle was obtained by oxidation with iodine. With metal alkoxides the chromium tricarbonyl complex of 2-(2-fluorophenyl)ethanol gave either mixtures (from which

  当在二甲亚砜中用叔丁醇钾处理时，3-（2-氟苯基）丙-1-醇的三羰基铬三价铬化合物经分子内快速亲核取代，得到相应的苯并二氢吡喃基配合物，然后通过氧化得到杂环。碘。用金属醇盐，2-（2-氟苯基）乙醇的三羰基铬铬络合物得到混合物（分子内亲核取代的产物没有分离出来）或分子间亲核取代的产物。
• Merging Grubbs second-generation catalyst with photocatalysis enables<i>Z</i>-selective metathesis of olefins: scope, limitations, and mechanism
  作者：Saïf Eddine Chérif、Avisek Ghosh、Saloua Chelli、Isabelle M. Dixon、Jamil Kraiem、Sami Lakhdar

  DOI：10.1039/d2sc03961c

  日期：——

  Olefin cross-metathesis is a cornerstone reaction in organic synthesis where stereoselectivity is typically governed by the structure of the catalyst. In this work, we show that merging Grubbs second generation catalyst, a classical E-selective catalyst, with a readily available photocatalyst, enables the exclusive formation of the contra-thermodynamic Z-isomer. The scope and limitations of this unprecedented

  烯烃交叉复分解是有机合成中的基石反应，其中立体选择性通常由催化剂的结构决定。在这项工作中，我们展示了将 Grubbs 第二代催化剂（一种经典的E选择性催化剂）与现成的光催化剂合并，能够独家形成反热力学Z异构体。基于计算和实验机制数据讨论了这种前所未有的方法的范围和局限性。
• Substituent effects of cis-cinnamic acid analogues as plant growh inhibitors
  作者：Keisuke Nishikawa、Hiroshi Fukuda、Masato Abe、Kazunari Nakanishi、Tomoya Taniguchi、Takashi Nomura、Chihiro Yamaguchi、Syuntaro Hiradate、Yoshiharu Fujii、Katsuhiro Okuda、Mitsuru Shindo

  DOI：10.1016/j.phytochem.2013.08.013

  日期：2013.12

  1-O-cis-Cinnamoyl-beta-D-glucopyranose is one of the most potent allelochemicals that has been isolated from Spiraea thunbergii Sieb by Hiradate et al. It derives its strong inhibitory activity from cis-cinnamic acid (cis-CA), which is crucial for phytotoxicity. By preparing and assaying a series of cis-CA analogues, it was previously found that the key features of cis-CA for lettuce root growth inhibition are a phenyl ring, cis-configuration of the alkene moiety, and carboxylic acid. On the basis of a structure-activity relationship study, the substituent effects on the aromatic ring of cis-CA were examined by systematic synthesis and the lettuce root growth inhibition assay of a series of cis-CA analogues having substituents on the aromatic ring. While ortho- and para-substituted analogues exhibited low potency in most cases, meta-substitution was not critical for potency, and analogues having a hydrophobic and sterically small substituent were more likely to be potent. Finally, several cis-CA analogues were found to be more potent root growth inhibitors than cis-CA. (C) 2013 Elsevier Ltd. All rights reserved.
• <i>Z</i>-Selective phosphine promoted 1,4-reduction of ynoates and propynoic amides in the presence of water
  作者：Fabian Seifert、Denis Drikermann、Johannes Steinmetzer、You Zi、Stephan Kupfer、Ivan Vilotijevic

  DOI：10.1039/d1ob00909e

  日期：——

  the selectivity by preventing or reducing the rates of Z- to E-product isomerization. Close reaction monitoring enables isolation of the Z-alkenes with high selectivities. The computational results suggest that the reactions could be highly Z-selective owing to the stereoselective formation of the E-P-hydroxyphosphorane intermediate.

  在水存在下，膦介导的取代丙炔酸酯和酰胺的还原产生了具有高Z选择性的部分还原的 α,β-不饱和酯和酰胺。在某些情况下，产物的竞争性原位 Z对E异构化降低了分离的 α,β-不饱和羰基产物的Z对E比。反应时间和反应混合物中的磷化氢和水的量是通过防止或降低Z - 至E -产物异构化速率来控制选择性的关键实验因素。密切的反应监测可以隔离Z-具有高选择性的烯烃。计算结果表明，由于EP -羟基正膦中间体的立体选择性形成，反应可能是高度Z选择性的。