3-(4-氯苯基)-1-(吡啶-2-基)丙-2-烯-1-酮 | 16231-98-4

• 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
• 中文名称: 3-(4-氯苯基)-1-(吡啶-2-基)丙-2-烯-1-酮
• 英文名称: (E)-3-(4-chlorophenyl)-1-(pyridin-2-yl)prop-2-en-1-one
• 英文别名: 3-(4-chlorophenyl)-1-(pyridin-2-yl)prop-2-en-1-one；(E)-3-(4-chlorophenyl)-1-pyridin-2-ylprop-2-en-1-one
• CAS: 16231-98-4
• 化学式: C₁₄H₁₀ClNO
• 分子量: 243.692
• InChiKey: CITDASDVSCSOTC-RMKNXTFCSA-N

物化性质

• 熔点：
  103-105 °C(Solv: ethanol (64-17-5))
• 沸点：
  404.8±45.0 °C(Predicted)
• 密度：
  1.249±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-氯苯基)-1-(吡啶-2-基)丙-2-烯-1-酮 在 乙酸铵 、 氢氧化钾 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 5-(4-chlorophenyl)-7-(pyridin-2-yl)-1H-pyrido[2,3-d]pyrimidine-2,4-dithione
  参考文献：
  名称：

  Preparation of Some Fused Pyridopyrimidine and Pyridothienotriazine Derivatives for Biological Evaluation

  摘要：

  Compounds 2 and 9 were formed using 3-(4-chloro-phenyl)-1-pyridin-2-yl propenone (1) and malononitrile or ethyl cyanoacetate, respectively. The pyridine derivative 2 was in turn used as a precursor for the preparation of some pyridopyrimidine and fused pyridopyrimidine derivatives 3-8. On the other hand, the pyridine derivative 9 was used for the preparation of thienopyridine derivatives 11 and 12. Nitrozation of compound 12 afforded pyridothienotriazine derivative 13. Some of the prepared products showed potent antimicrobial activity.

  DOI：

  10.1080/104265090968118
• 作为产物：
  描述：

  2-乙酰基吡啶 、 4-氯苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以94%的产率得到3-(4-氯苯基)-1-(吡啶-2-基)丙-2-烯-1-酮
  参考文献：
  名称：

  水中狄尔斯-阿尔德反应的路易斯酸催化

  摘要：

  在这里，我们报告了由路易斯酸在水中催化的狄尔斯-阿尔德 (DA) 反应的首次详细研究。Co2+、Ni2+、Cu2+ 和 Zn2+ 离子作为路易斯酸催化剂对双齿亲二烯体 3-苯基-1-(2-吡啶基)-2-丙烯-1-酮之间 DA 反应的速率和内-外选择性的影响已经研究了水中的 (1a-e) 和环戊二烯 (2)。相对于乙腈中的未催化反应，水中 0.010 M CU(NO3)(2) 的催化作用可将反应加速 79 300 倍。根据路易斯酸络合的平衡常数分析催化反应的动力学具有 1a-e 和所得配合物与 2 反应的速率常数。水对底物 1 与 2 的未催化 DA 反应的速率增强比催化反应明显得多。对于路易斯酸催化的反应，在未催化过程中由水引起的内-外选择性的增加完全不存在。对催化反应观察到的适度的溶剂和取代基效应表明活化过程中电荷分离的变化不大于未催化反应的相应变化。

  DOI：

  10.1021/ja960318k

文献信息

• [EN] ALLOSTERIC PROTEIN KINASE MODULATORS<br/>[FR] MODULATEURS DE PROTÉINE KINASE ALLOSTÉRIQUE
  申请人：UNIV SAARLAND

  公开号：WO2010043711A1

  公开（公告）日：2010-04-22

  The invention provides specific small molecule compounds that allosterically regulate the activity or modulate protein-protein interactions of AGC protein kinases and the Aurora family of protein kinases, methods for their production, pharmaceutical compositions comprising same, and their use for preparing medicaments for the treatment and prevention of diseases related to abnormal activities of AGC protein kinases or of protein kinases of the Aurora family.

  该发明提供特定的小分子化合物，这些化合物能够变构调节AGC蛋白激酶的活性或调节Aurora家族蛋白激酶的蛋白-蛋白相互作用，提供这些化合物的制备方法，包含这些化合物的药物组合物，以及它们用于制备治疗和预防与AGC蛋白激酶或Aurora家族蛋白激酶异常活动相关疾病的药物的应用。
• ALLOSTERIC PROTEIN KINASE MODULATORS
  申请人：Engel Matthias

  公开号：US20120046307A1

  公开（公告）日：2012-02-23

  The invention provides specific small molecule compounds that allosterically regulate the activity or modulate protein-protein interactions of AGC protein kinases and the Aurora family of protein kinases, methods for their production, pharmaceutical compositions comprising same, and their use for preparing medicaments for the treatment and prevention of diseases related to abnormal activities of AGC protein kinases or of protein kinases of the Aurora family.

  本发明提供了特定的小分子化合物，它们通过变构调节AGC蛋白激酶的活性或调节Aurora家族蛋白激酶的蛋白质-蛋白质相互作用，其生产方法，包含该化合物的药物组合物，以及它们用于制备治疗和预防与AGC蛋白激酶或Aurora家族蛋白激酶异常活动相关疾病的药物的应用。
• Phenyl-substituted 2,2′:6′,2″-terpyridine as a new series of fluorescent compounds—their photophysical properties and fluorescence tuning
  作者：Toshiki Mutai、Jin-Dong Cheon、Shinpei Arita、Koji Araki

  DOI：10.1039/b102685m

  日期：——

  Several phenyl-substituted 2,2′:6′,2″-terpyridines (tpy) were synthesized and it was found that 4′-phenyl tpy (ptp, 3) exhibited the most effective fluorescence, whose quantum yield was up to 0.64 in cyclohexane. For further study on tuning the fluorescence properties of ptp, different substituents were introduced into the p-position of the phenyl group. While Br- 10, Cl- 11, and CH3-ptp 12 showed their absorption and fluorescence in the same region as 3, those of NH2- 14 and Me2N-ptp 15 were observed at much longer wavelengths. In addition, fluorescence maxima of 14 and 15 showed large (>130 nm) solvent dependence. The difference between ground and excited state dipole moment (Δμ) for 15 was estimated to be 15.2 D by the Lippert–Mataga equation, indicating the intramolecular charge transfer (ICT) process. Semi-empirical MO calculation (MOPAC/AM1) demonstrated that the HOMO-1, HOMO and LUMO of 3, 10–12 were mainly localized on the phenyl (πph), tpy (πtpy) and tpy (π*tpy) part, respectively, indicating that the lowest energy absorption band of 3, 10–12 was the local excitation (πtpy–π*tpy). In the case of 14 and 15, which have an electron-donating substituent, πph instead of πtpy became the HOMO. Thus, the lowest energy absorption of 14 and 15 was an ICT transition (πph–π*tpy), and a large red shift of the fluorescence occurred. In these compounds, the energy level of πph is controlled without affecting that of πtpy and π*tpy, suggesting a novel approach for tuning the color of fluorescence.

  合成了几种苯基取代的2,2':6',2''-三联吡啶（tpy），发现4'-苯基tpy（ptp，3）具有最有效的荧光，其在环己烷中的量子产率高达0.64。为了进一步研究调节ptp的荧光性质，将不同的取代基引入苯环的p位。Br-10，Cl-11和CH3-ptp 12显示与3相同的吸收和荧光区域，而NH2-14和Me2N-ptp 15的吸收和荧光则在更长的波长处被观察到。此外，14和15的荧光最大值显示了大于130 nm的溶剂依赖性。根据Lippert-Mataga方程，15的基态和激发态偶极矩差（Δμ）估计为15.2 D，表明存在分子内电荷转移（ICT）过程。半经验MO计算（MOPAC/AM1）表明，3、10-12的HOMO-1、HOMO和LUMO主要分别定域在苯基（πph）、tpy（πtpy）和tpy（π*tpy）部分，表明3、10-12的最低能量吸收带是局部激发（πtpy-π*tpy）。对于具有电子给体取代基的14和15，πph而非πtpy成为HOMO。因此，14和15的最低能量吸收是ICT跃迁（πph-π*tpy），并发生了大幅度的荧光红移。在这些化合物中，πph的能级可以在不影响πtpy和π*tpy能级的情况下进行调控，这为调节荧光颜色提供了一种新方法。
• N-Heterocyclic carbene-catalyzed diastereoselective synthesis of β-lactone-fused cyclopentanes using homoenolate annulation reaction
  作者：Subrata Mukherjee、Santigopal Mondal、Atanu Patra、Rajesh G. Gonnade、Akkattu T. Biju

  DOI：10.1039/c5cc02960k

  日期：——

  NHC-catalyzed annulation of enals with 2-enoylpyridines or 2-enoylpyridine N-oxides leading to the diastereoselective synthesis of [small beta]-lactone-fused cyclopentanes is reported. The reaction proceeds via the generation of homoenolate equivalent intermediates and...

  据报道，NHC用2-烯丙基吡啶或2-烯丙基吡啶N-氧化物环氧化烯类，导致β-内酯小环戊烷的非对映选择性合成。该反应通过生成均烯酸酯等效中间体和...进行。
• Highly Efficient Mechanochemical Reactions of 1,3-Dicarbonyl Compounds with Chalcones and Azachalcones Catalyzed by Potassium Carbonate
  作者：Guan-Wu Wang、Ze Zhang、Ya-Wei Dong、Koichi Komatsu

  DOI：10.1055/s-2003-43350

  日期：——

  Under the high-speed vibration milling conditions, K2CO3 was found to be a very efficient catalyst for the solvent-free Michael reactions of 1,3-dicarbonyl compounds with chalcones and azachalcones. In most cases, conventional side reactions were avoided and thus excellent yields were achieved. The influences of other catalysts and the vibration frequency on the Michael reaction were investigated.

  在高速振动研磨条件下，发现K2CO3是一种非常有效的催化剂，能够无溶剂地促进1,3-二酮化合物与查尔酮和阿扎查尔酮之间的迈克尔反应。在大多数情况下，避免了常规的副反应，从而实现了优异的产率。研究了其他催化剂和振动频率对迈克尔反应的影响。