(E)-1-(4-iodophenyl)-3-phenylprop-2-en-1-one | 7466-60-6

• 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: (E)-1-(4-iodophenyl)-3-phenylprop-2-en-1-one
• 英文别名: 2-Propen-1-one, 1-(4-iodophenyl)-3-phenyl-
• CAS: 7466-60-6
• 化学式: C₁₅H₁₁IO
• 分子量: 334.156
• InChiKey: CEPMBXDQWOVRER-IZZDOVSWSA-N

物化性质

• 熔点：
  115 °C
• 沸点：
  417.8±45.0 °C(Predicted)
• 密度：
  1.576±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 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：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-1-(4-iodophenyl)-3-phenylprop-2-en-1-one 在 三氟化硼乙醚 、 ammonium acetate 、 三乙胺 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 正丁醇 为溶剂， 反应 84.0h， 生成 5,5-difluoro-3,7-bis(4-iodophenyl)-1,9-diphenyl-5H-5l4-dipyrrolo[1,2-c:2',1'-f][1,3,5,2]triazaborinin-4-ium
  参考文献：
  名称：

  Highly near-infrared photoluminescence from aza-borondipyrromethene-based conjugated polymers

  摘要：

  AbstractNear‐infrared (NIR) emissive conjugated polymers were prepared by palladium‐catalyzed Sonogashira polymerization of diiodobenzene‐functionalized aza‐borondipyrromethene (Aza‐BODIPY) monomers, which were substituted at 3 and 5 or 1 and 7 positions on the Aza‐BODIPY core, with 1,4‐diethynyl‐2,5‐dihexadecyloxybenzene or 3,3′‐didodecyl‐2,2′‐diethynyl‐5,5′‐bithiophene. The structures of the polymers were confirmed by 1H NMR, 13C NMR, 11B NMR, Fourier transform infrared (FT‐IR) spectroscopies, and size exclusion chromatography (SEC). The optical properties were then characterized by UV–vis absorption and photoluminescence (PL) spectroscopies, and theoretical calculation using density‐functional theory (DFT) method. The polymers were fusible and soluble in common organic solvents including tetrahydrofuran (THF), o‐xylene, toluene, CHCl3, and CH2Cl2, etc. The UV–vis absorption and PL spectra of the polymers shifted to long wavelength region in comparison with simple Aza‐BODIPY as the counterpart because of extended π‐conjugation of the polymers. The polymers efficiently emitted NIR light with narrow emission bands at 713∼777 nm on excitation at each absorption maximum. Especially, the polymer attached 1,4‐diethynyl‐2,5‐dihexadecyloxybenzene to 3,5‐position on the core revealed intense quantum yields (ϕF = 24%) in this NIR region (753 nm). © 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2010

  DOI：

  10.1002/pola.24335
• 作为产物：
  描述：

  4-碘代苯乙酮 、 苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以63 %的产率得到(E)-1-(4-iodophenyl)-3-phenylprop-2-en-1-one
  参考文献：
  名称：

  镍催化芳基/烯基卤化物与烷基异氰化物的氰化反应

  摘要：

  我们在此描述了芳基/烯基卤化物与烷基异氰化物的镍催化氰化反应。发现芳基/烯基碘和溴化物都是与烷基异氰化物反应的有效亲电子试剂，以中等至良好的产率提供腈化合物。包括卤素以及羟基、甲酰基和乙酰氨基在内的一系列官能团与镍催化相当兼容。该协议具有广泛的官能团耐受性、简单的反应条件和克级合成。

  DOI：

  10.1039/d2ob01240e

文献信息

• Iron-Facilitated Oxidative Radical Decarboxylative Cross-Coupling between α-Oxocarboxylic Acids and Acrylic Acids: An Approach to α,β-Unsaturated Carbonyls
  作者：Qing Jiang、Jing Jia、Bin Xu、An Zhao、Can-Cheng Guo

  DOI：10.1021/acs.joc.5b00267

  日期：2015.4.3

  The first Fe-facilitated decarboxylative cross-coupling reaction between α-oxocarboxylic acids and acrylic acids in aqueous solution has been developed. This transformation is characterized by its wide substrate scope and good functional group compatibility utilizing inexpensive and easily accessible reagents, thus providing an efficient and expeditious approach to an important class of α,β-unsaturated

  已经开发出水溶液中α-氧代羧酸与丙烯酸之间的第一个铁促进的脱羧交叉偶联反应。该转化的特征在于其底物范围宽和使用廉价且易于获得的试剂的良好官能团相容性，从而为生物活性化合物中常见的重要一类α，β-不饱和羰基化合物提供了一种有效而快捷的方法。在随后的官能化反应中也证明了偶联产物的合成潜力。初步的机理研究表明，该过程涉及自由基途径：
• Ruthenium-Catalyzed Conjugate Hydrogenation of α,β-Enones by in situ Generated Dihydrogen from Paraformaldehyde and Water
  作者：Wanfang Li、Xiao-Feng Wu

  DOI：10.1002/ejoc.201403359

  日期：2015.1

  Notwithstanding that the highly selective hydrogenation of α,β-enones to allylic alcohols can be realized by using Noyori's Ru bifunctional system, the selective reduction of the C=C bonds in α,β-enones without touching the C=O bonds still lacks a general, simple, and efficient procedure. Ruthenium-catalyzed conjugate hydrogenation of various α,β-enones to saturated ketones with high selectivity was investigated

  尽管使用 Noyori 的 Ru 双功能系统可以实现 α,β-烯酮向烯丙醇的高度选择性氢化，但在不接触 C=O 键的情况下选择性还原 α,β-烯酮中的 C=C 键仍然缺乏通用、简单、高效的程序。研究了钌催化的各种α,β-烯酮以高选择性共轭氢化成饱和酮。该程序最重要的特点是由多聚甲醛（或福尔马林）和水原位产生的氢气用作还原剂。
• [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。
• Solvent-free synthesis, spectral correlations and antimicrobial activities of some aryl E 2-propen-1-ones
  作者：K. Sathiyamoorthi、V. Mala、S.P. Sakthinathan、D. Kamalakkannan、R. Suresh、G. Vanangamudi、G. Thirunarayanan

  DOI：10.1016/j.saa.2013.04.048

  日期：2013.8

  Totally 38 aryl E 2-propen-1-ones including nine substituted styryl 4-iodophenyl ketones have been synthesised using solvent-free SiO2-H3PO4 catalyzed Aldol condensation between respective methyl ketones and substituted benzaldehydes under microwave irradiation. The yields of the ketones are more than 80%. The synthesised chalcones were characterized by their analytical, physical and spectroscopic

  在微波辐射下，使用无溶剂的SiO2-H3PO4催化的Aldol缩合反应，合成了38个芳基E 2-丙-1-酮，其中包括9个取代的苯乙烯基4-碘苯基酮。酮的产率超过80％。合成的查耳酮以其分析，物理和光谱数据为特征。使用单线性回归分析，已合成的取代苯乙烯基4-碘苯基酮的光谱频率已与哈米特取代基常数，F和R参数相关联。使用Bauer-Kirby方法研究了4-碘苯基查耳酮的抗菌活性。