(Z)-2-fluoro-3-(4-methoxyphenyl)-1-phenyl-2-propen-1-one | 126912-57-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (Z)-2-fluoro-3-(4-methoxyphenyl)-1-phenyl-2-propen-1-one
• 英文别名: (Z)-2-fluoro-3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one
• CAS: 126912-57-0
• 化学式: C₁₆H₁₃FO₂
• 分子量: 256.276
• InChiKey: NYOAIXIRSRZXJO-PTNGSMBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E/Z)-1-chloro-1,2-difluoro-2-phenylethene 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成 (Z)-2-fluoro-3-(4-methoxyphenyl)-1-phenyl-2-propen-1-one
  参考文献：
  名称：

  Yarmolenko, S. N.; Fialkov, Yu. A.; Yagupol'skii, L. M., Journal of Organic Chemistry USSR (English Translation), 1989, vol. 25, # 9.2, p. 1767 - 1774

  摘要：

  DOI：

文献信息

• Synthesis of α-fluoroketones and α-fluoroenones in aqueous media
  作者：Yan He、Xinying Zhang、Nana Shen、Xuesen Fan

  DOI：10.1016/j.jfluchem.2013.08.006

  日期：2013.12

  An efficient synthesis of α-fluoroketones via the nucleophilic fluorination of α-bromoketones in water with TBAF·3H2O as the fluorinating agent was developed in this paper. In addition, a simple and efficient synthesis of α-fluoroenones through the condensation of α-fluoroketones with aldehydes promoted by sodium hydroxide in water was also discovered.

  α-氟酮的高效合成经由α-溴酮在水中的亲核氟化用TBAF·3H 2 O作为氟化剂是在本文开发的。此外，通过α-氟酮与由氢氧化钠在水中促进醛的缩合简单和α-fluoroenones的有效合成还发现。
• An efficient synthesis of (Z)-α-fluorochalcones via the palladium-catalyzed cross-coupling reaction of (Z)-α-fluorocinnamoyl chloride with boronic acids
  作者：Said Eddarir、Mohammed Kajjout、Christian Rolando

  DOI：10.1016/j.tet.2012.12.025

  日期：2013.2

  An efficient synthesis of α-fluorochalcones (1,3-diphenyl-2-fluoroprop-2-en-1-one) based on the Suzuki–Miyaura palladium-catalyzed cross-coupling reaction of arylboronic acids with α-fluorocinnamoyl chlorides in the presence of Cs2CO3 in toluene is described. This approach allows the synthesis of fluorinated analogues of functionalized natural chalcones.

  在存在的情况下，基于铃木-宫浦钯催化的芳基硼酸与α-氟肉桂酰氯的交叉偶联反应，可高效合成α-氟代查耳酮（1,3-二苯基-2-氟代丙-2-烯-1-酮）描述了甲苯中Cs 2 CO 3的含量。这种方法可以合成功能化天然查耳酮的氟化类似物。
• Copper and Palladium Cocatalyzed Defluorinative Coupling of <i>gem</i>-Difluoroalkenes and Acyl Chloride
  作者：Xinyu Liu、Juanjuan Wu、Chun Zhang

  DOI：10.1021/acs.orglett.3c00347

  日期：2023.3.10

  A novel copper and palladium cocatalyzed defluorinative coupling of gem-difluoroalkenes and acyl chlorides has been developed. It is a practical method to prepare α-fluorochalcones, which are a kind of important unit in a variety of bioactive compounds. Under mild reaction conditions, a series of substrates with various functional groups could afford desired products smoothly. Further synthetic studies

  开发了一种新型的铜和钯助催化的偕二氟烯烃和酰氯的脱氟偶联反应。α-氟查耳酮是多种生物活性化合物中的重要单元，是制备α-氟查耳酮的实用方法。在温和的反应条件下，一系列具有不同官能团的底物可以顺利地得到所需的产物。进一步的合成研究表明，这种化学产物可以用作多功能前体来获得复杂的化合物。此外，基于控制实验提出了反应机理。
• α-Fluorovinyl Weinreb Amides and α-Fluoroenones from a Common Fluorinated Building Block
  作者：Arun K. Ghosh、Shaibal Banerjee、Saikat Sinha、Soon Bang Kang、Barbara Zajc

  DOI：10.1021/jo802784w

  日期：2009.5.15

  Synthesis and reactivity of N-methoxy-N-methyl-(1,3-benzothiazol-2-ylsulfonyl)fluoroacetamide, a building block for Julia olefination, is reported. This reagent undergoes condensation reactions with aldehydes and cyclic ketones to give alpha-fluorovinyl Weinreb amides. Olefination reactions proceed under mild, DBU-mediated conditions, or in the presence of NaH. DBU-mediated condensations proceed with either E- or Z-selectivity, depending upon reaction conditions, whereas NaH-mediated reactions are >= 98% Z-stereoselective. Conversion of the Weinreb amide moiety in N-methoxy-N-methyl-(1,3-benzothiazol-2-ylsulfanyl)fluoroacetamide to ketones, followed by oxidation, resulted in another set of olefination reagents, namely (1,3-benzothiazol-2-ylsulfonyl)fluoromethyl phenyl and propyl ketones. In the presence of DBU, these compounds react with aldehydes tested to give alpha-fluoroenones with high Z-selectivity. The use of N-methoxy-N-methyl-(1,3-benzothiazol-2-ylsulfanyl)fluoroacetamide as a common fluorinated intermediate in the synthesis of alpha-fluorovinyl Weinreb amides and alpha-fluoroenones has been demonstrated. Application of the Weinreb amide to alpha-flu-fluoro allyl amine synthesis is also shown.
• YARMOLENKO, S. N.;FIALKOV, YU. A.;YAGUPOLSKIJ, L. M., ZH. ORGAN. XIMII, 25,(1989) N, S. 1955-1962
  作者：YARMOLENKO, S. N.、FIALKOV, YU. A.、YAGUPOLSKIJ, L. M.

  DOI：——

  日期：——