3-(4-cyanophenyl)-1-(4-methylphenyl)-2-propen-1-one | 62584-58-1

• 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: 3-(4-cyanophenyl)-1-(4-methylphenyl)-2-propen-1-one
• 英文别名: 4-[3-(4-Methylphenyl)-3-oxoprop-1-enyl]benzonitrile
• CAS: 62584-58-1
• 化学式: C₁₇H₁₃NO
• 分子量: 247.296
• InChiKey: KDFIDEMXURYTFD-UHFFFAOYSA-N

物化性质

• 熔点：
  179-182 °C(Solv: ethanol (64-17-5))
• 沸点：
  447.7±45.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-cyanophenyl)-1-(4-methylphenyl)-2-propen-1-one 在 溶剂黄146 、 锌 作用下， 以 丙酮 为溶剂， 生成 4-(3-oxo-3-p-tolylpropyl)benzonitrile
  参考文献：
  名称：

  Wagner; Voigt, Pharmazie, 1976, vol. 31, # 8, p. 528 - 532

  摘要：

  DOI：
• 作为产物：
  描述：

  对甲基苯乙酮 、 4-氰基苯甲醛 在 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 0.5h， 以49%的产率得到3-(4-cyanophenyl)-1-(4-methylphenyl)-2-propen-1-one
  参考文献：
  名称：

  完全和不同丙烯酸化吡啶的三步合成

  摘要：

  在空气中存在FeCl 3的情况下，β-（2-吡啶基）烯胺和α，β-不饱和酮的缩合得到高度取代的吡啶。因此，仅通过三个步骤就可以通过简单的实验操作从市售试剂中合成不同取代的五芳基吡啶。

  DOI：

  10.1002/ejoc.201901663

文献信息

• [EN] 2,3,5 TRISUBSTITUTED PYRROLE DERIVATIVES AS TOPOISOMERASE INHIBITORS AND THERAPEUTIC USES THEREOF<br/>[FR] DÉRIVÉS TRISUBSTITUÉS 2, 3, 5 DE PYRROLE EN TANT QU'INHIBITEURS DE TOPOISOMÉRASE ET LEURS UTILISATIONS THÉRAPEUTIQUES
  申请人：UNIV OF MYSORE

  公开号：WO2017029684A1

  公开（公告）日：2017-02-23

  The compounds of Formula (1) having topoisomerase inhibitory effect includes [Formula should be inserted here] wherein, R1 is selected from a group consisting of H, OR5, optionally substituted C1-C12 alkyl, haloalkyl, C2-C12alkenyl, C2-C12alkynyl, C1-C12alkyloxy, C1-C12haloalkyloxy, C2-C10 heteroalkyl, C3- C12 cycloalkyl, C3-C12cycloalkenyl, C2- C12heterocycloalkyl, C2-C2 heterocycloalkenyl, C6-C18aryl, and C1-C18heteroaryl; R2, R3 and R4 are independently selected from a group consisting of H, halogen, CN, - NO2, SH, CF3, OH, CO2H, CONH2, OCF3, optionally substituted C1-C12alkyl, optionally substituted C1-C12haloalkyl optionally substituted C2-C12alkenyl, optionally substituted C2- C12alkynyl, optionally substituted C1-C12alkyloxy, optionally substituted C1- C12haloalkyloxy, optionally substituted C2-C12heteroalkyl, optionally substituted C3- C12cycloalkyl, optionally substituted C3-C12 cycloalkenyl, optionally substituted C2-C12 heterocycloalkyl, optionally substituted C2-C12 heterocycloalkenyl, optionally substituted C6- C18aryl, and optionally substituted C1-C18heteroaryl; R5 is selected H, optionally substituted C1-C12alkyl, optionally substituted C2- C12alkenyl, optionally substituted optionally substituted C1-C12 haloalkyl, optionally substituted C3-C12cycloalkyl, optionally substituted C6- C18aryl, and optionally substituted C1- Ci18heteroaryl; or a pharmaceutically acceptable salt, N-oxide, or prodrug thereof.

  具有拓扑异构酶抑制作用的Formula（1）化合物包括[在此插入公式]其中，R1从以下组中选择：H，OR5，可选择取代的C1-C12烷基，卤代烷基，C2-C12烯基，C2-C12炔基，C1-C12烷氧基，C1-C12卤代烷氧基，C2-C10杂基烷基，C3-C12环烷基，C3-C12环烯基，C2-C12杂环烷基，C2-C2杂环烯基，C6-C18芳基和C1-C18杂芳基；R2、R3和R4分别从以下组中选择：H，卤素，CN，-NO2，SH，CF3，OH，CO2H，CONH2，OCF3，可选择取代的C1-C12烷基，可选择取代的C1-C12卤代烷基，可选择取代的C2-C12烯基，可选择取代的C2-C12炔基，可选择取代的C1-C12烷氧基，可选择取代的C1-C12卤代烷氧基，可选择取代的C2-C12杂基烷基，可选择取代的C3-C12环烷基，可选择取代的C3-C12环烯基，可选择取代的C2-C12杂环烷基，可选择取代的C2-C12杂环烯基，可选择取代的C6-C18芳基，可选择取代的C1-C18杂芳基；R5选择为H，可选择取代的C1-C12烷基，可选择取代的C2-C12烯基，可选择取代的可选择取代的C1-C12卤代烷基，可选择取代的C3-C12环烷基，可选择取代的C6-C18芳基，可选择取代的C1-Ci18杂芳基；或其药学上可接受的盐、N-氧化物或前药。
• Three Step Synthesis of Fully and Differently Arylated Pyridines
  作者：Mao Arita、Soichi Yokoyama、Haruyasu Asahara、Nagatoshi Nishiwaki

  DOI：10.1002/ejoc.201901663

  日期：2020.1.31

  Condensation of β‐(2‐pyridyl)enamine and α,β‐unsaturated ketone in the presence of FeCl3 under air afforded highly substituted pyridines. Synthesis of differently substituted pentaarylpyridines was consequently achieved via only three steps from commercially available reagents with simple experimental manipulations.

  在空气中存在FeCl 3的情况下，β-（2-吡啶基）烯胺和α，β-不饱和酮的缩合得到高度取代的吡啶。因此，仅通过三个步骤就可以通过简单的实验操作从市售试剂中合成不同取代的五芳基吡啶。
• Monofunctionalized 1,3,5,7-TetraarylazaBODIPYs and Their Application in the Synthesis of AzaBODIPY Based Conjugates
  作者：Angira Koch、Mangalampalli Ravikanth

  DOI：10.1021/acs.joc.9b01311

  日期：2019.9.6

  A series of monofunctionalized 1,3,5,7-tetraarylazaBODIPYs containing functional groups such as p-hydroxymethyl phenyl, p-hydroxy-phenyl, p-cyanophenyl, p-nitrophenyl, and p-formylphenyl groups at the 1-position of the azaBODIPY core were synthesized by mixed condensation of two different nitrochalcones in n-butanol in the presence of CH3COONH4 at reflux followed by complexation with BF3 center dot OEt2. The mixed condensation of nitrochalcones resulted in the formation of three different dipyrromethenes, which was treated with BF3 center dot OEt2 to afford the desired monofunctionalized tetraarylazaBODIPYs in 30-36% yields. To demonstrate the application of monofunctionalized tetraarylazaBODIPYs, we reacted monoformyl functionalized tetraarylazaBODIPY with excess pyrrole to afford mono-dipyrromethanyl-substituted tetraarylazaBODIPY, which was used as a key precursor to prepare novel covalently linked azaBODIPY-based conjugates. The mono-dipyrromethanyl azaBODIPY was in situ oxidized with 2,3-dichloro-5,6-dicyanobenzoquinone and either reacted with BF3 center dot OEt2 to afford azaBODIPY-BODIPY conjugates or reacted with metal salt such as Pd(acac) 2 to afford azaBODIPY-Pd(II)dipyrrin conjugates. Alternately, dipyrromethanyl- substituted azaBODIPY was condensed with dipyrromethane dicarbinol or 16-oxatripyrrane under mild acid catalyzed conditions followed by oxidation and chromatographic purification to afford azaBODIPY-porphyrin or azaBODIPY-oxasmaragdyrin conjugates, respectively. The photophysical studies on conjugates revealed that azaBODIPY is a good energy acceptor and invoked the possibility of energy transfer from the donor to acceptor in covalently linked conjugates.
• Wagner; Voigt, Pharmazie, 1976, vol. 31, # 8, p. 528 - 532
  作者：Wagner、Voigt

  DOI：——

  日期：——
• Synthesis of Chalcones and Pyrazolines Using NB-Fe3O4@SiO2@CPTMO@DEA-SO3H as an Efficient and Reusable Nanocatalyst
  作者：P. Ghorbani、M. Nasr-Esfahani、B. Eftekhari Far

  DOI：10.1134/s1070428022120107

  日期：2022.12