2-benzoyl-3-(4-fluorophenyl)but-2-enenitrile | 1146188-82-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-benzoyl-3-(4-fluorophenyl)but-2-enenitrile
• CAS: 1146188-82-0
• 化学式: C₁₇H₁₂FNO
• 分子量: 265.287
• InChiKey: IVWUNJSSFZOORZ-UHFFFAOYSA-N

物化性质

• 沸点：
  390.9±42.0 °C(predicted)
• 密度：
  1.186±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.01
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  40.86
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-benzoyl-3-(4-fluorophenyl)but-2-enenitrile 、 3-亚苄基-2,4-戊二酮 在 caesium carbonate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以62%的产率得到6'-acetyl-4''-fluoro-5'-methyl-[1,1':3',1''-terphenyl]-4'-carbonitrile
  参考文献：
  名称：

  碱促进的串联环化，通过CC键构建苯甲腈的合成

  摘要：

  通过碱促进的具有吸电子基团（EWG）的α，β-不饱和烯酮和2酰基丙烯腈的串联促进环化反应，可以轻松合成苯甲腈。这种获取苯甲腈的新合成方法适用于多种底物。在先前的文献和我们自己的研究的基础上，提出了一种合理的反应机理。

  DOI：

  10.1002/adsc.201701329
• 作为产物：
  描述：

  4-氟苯乙酮 、 苯甲酰乙腈 在 四氯化钛 、 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 2-benzoyl-3-(4-fluorophenyl)but-2-enenitrile
  参考文献：
  名称：

  碱促进的串联环化，通过CC键构建苯甲腈的合成

  摘要：

  通过碱促进的具有吸电子基团（EWG）的α，β-不饱和烯酮和2酰基丙烯腈的串联促进环化反应，可以轻松合成苯甲腈。这种获取苯甲腈的新合成方法适用于多种底物。在先前的文献和我们自己的研究的基础上，提出了一种合理的反应机理。

  DOI：

  10.1002/adsc.201701329

文献信息

• Direct Assembly of Polysubstituted Naphthalenes via a Tandem Reaction of Benzynes and α-Cyano-β-methylenones
  作者：Qiang Wang、Yi An、Guangfen Du、Zhi-Hua Cai、Bin Dai、Lin He

  DOI：10.1021/acs.joc.0c01975

  日期：2020.11.6

  A mild and transition-metal-free benzannulation reaction for the construction of the naphthalene skeleton has been described. Benzynes react with α-cyano-β-alkylenones through a tandem nucleophilic addition/cyclization/aromatization process to afford polysubstituted naphthalenes in 50–94% yields.

  已经描述了用于构建萘骨架的温和且无过渡金属的苯环反应。苯甲酮通过串联亲核加成/环化/芳构化过程与α-氰基-β-烷基烯酮反应，以50-94％的产率提供多取代的萘​​。
• Phosphine-Catalyzed Enantioselective [4 + 2] Cycloaddition–Semipinacol-Type-Rearrangement Reaction of Morita–Baylis–Hillman Carbonates
  作者：Yuan Zhong、Xiaoyun Zhao、Lu Gan、Sihua Hong、Xianxing Jiang

  DOI：10.1021/acs.orglett.8b01661

  日期：2018.7.20

  The chiral phosphine-triggered electrophilic ylide intermediate for a Morita–Baylis–Hillman carbonates activation strategy provides a promising method for the design of organocatalytic intermolecular higher-order annulation processes.

  Morita–Baylis–Hillman碳酸盐活化策略的手性膦触发的亲电性叶立德中间体为有机催化分子间高阶环化工艺的设计提供了一种有前途的方法。
• Assembly of unsymmetrical 1,3,5-triarylbenzenes <i>via</i> tandem reaction of β-arylethenesulfonyl fluorides and α-cyano-β-methylenones
  作者：Fang Zhang、Yi An、Jichang Liu、Guangfen Du、Zhihua Cai、Lin He

  DOI：10.1039/d2nj01549h

  日期：——

  A transition-metal-free method has been proposed for the synthesis of unsymmetrical 1,3,5-triarylbenzenes via a tandem Diels–Alder cycloaddition/SuFEx/elimination process.

  一种无过渡金属的方法已被提出，用于通过串联Diels-Alder环加成/SuFEx/消除过程合成不对称的1,3,5-三芳基苯。
• Phosphine-Catalyzed Addition/Cycloaddition Domino Reactions of β′-Acetoxy Allenoate: Highly Stereoselective Access to 2-Oxabicyclo[3.3.1]nonane and Cyclopenta[a]pyrrolizine
  作者：Yiting Gu、Pengfei Hu、Chunjie Ni、Xiaofeng Tong

  DOI：10.1021/jacs.5b03273

  日期：2015.5.20

  Two classes of phosphine-catalyzed addition/cycloaddition domino reactions of beta'-acetoxy allenoate 1 have been developed. The reaction of 1 with 2-acyl-3-methyl-acrylonitrile 2 readily occurs to give 2-oxabicyclo[3.3.1]nonane 3, furnishing the beta'-addition/[4 + 4] cycloaddition domino sequence. In this sequence, beta'C of allenoate 1 is an electrophilic center, and its beta'C and gamma C serve as a 1,4-dipole. When the other reaction partner is switched to 2-acyl-3-(2-pyrrole)-acrylonitrile 8, a gamma-addition/[3 + 2] cycloaddition domino reaction is instead observed, in which allenoate 1 exhibits dual electrophilic reactivity of gamma C and 1,3-dipole chemical behavior of beta C and beta'C. Furthermore, both of these two asymmetric variants have also been achieved with up to 93% ee. The domino reactions presented in this report are valuable for highly stereoselective construction of complex structures under mild reaction conditions.
• Allosteric Modulators of the Adenosine A₁ Receptor: Synthesis and Pharmacological Evaluation of 4-Substituted 2-Amino-3-benzoylthiophenes
  作者：Luigi Aurelio、Celine Valant、Bernard L. Flynn、Patrick M. Sexton、Arthur Christopoulos、Peter J. Scammells

  DOI：10.1021/jm9002582

  日期：2009.7.23

  A series of 4-substituted 2-amino-3-benzoylthiophenes was screened using a functional assay of A A(1)AR-mediated phosphorylation of ERK 1/2 in intact CHO cells to identify both potential agonistic effects as well the ability to allosterically modulate the activity of the orthosteric agonist, R-PIA. More detailed concentration-response experiments were subsequently performed on two compounds (9a and 9o) utilizing both the ERK 1/2 assay as well as a second assay of [S-35]GTP gamma S binding to activated G proteins.