2-(4-iodophenyl)-5-phenyl-1,3,4-oxadiazole | 92151-21-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4-iodophenyl)-5-phenyl-1,3,4-oxadiazole
• CAS: 92151-21-8
• 化学式: C₁₄H₉IN₂O
• 分子量: 348.143
• InChiKey: IQLYNDORPHDZMV-UHFFFAOYSA-N

物化性质

• 熔点：
  158-158.5 °C
• 沸点：
  434.0±47.0 °C(Predicted)
• 密度：
  1.647±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-iodophenyl)-5-phenyl-1,3,4-oxadiazole 在 palladium diacetate 、 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基乙酰胺 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  1,3,4-Oxadiazole-Containing Histone Deacetylase Inhibitors: Anticancer Activities in Cancer Cells

  摘要：

  We describe 1,3,4-oxadiazole-containing hydroxamates (2) and 2-aminoanilides (3) as histone deacetylase inhibitors. Among them, 2t, 2x, and 3i were the most potent and selective against HDAC1. In U937 leukemia cells, 2t was more potent than SAHA in inducing apoptosis, and 3i displayed cell differentiation with a potency similar to MS-275. In several acute myeloid leukemia (AML) cell lines, as well as in U937 cells in combination with doxorubicin, 3i showed higher antiproliferative effects than SAHA.

  DOI：

  10.1021/jm500303u
• 作为产物：
  描述：

  Benzoic acid [1-(4-iodo-phenyl)-meth-(E)-ylidene]-hydrazide 在 potassium permanganate 作用下， 以 水 、 丙酮 为溶剂， 反应 0.17h， 以95%的产率得到2-(4-iodophenyl)-5-phenyl-1,3,4-oxadiazole
  参考文献：
  名称：

  微波辅助合成2,5-二取代1,3,4-恶二唑

  摘要：

  通过在固体矿物载体的表面上以及在丙酮和水的混合物中于微波辐射下用高锰酸钾氧化1-芳基-2-亚芳基肼来合成2,5-二取代的1,3,4-恶二唑。

  DOI：

  10.1016/j.tetlet.2004.09.095

文献信息

• ¹⁷ O NMR studies of substituted 1,3,4-oxadiazoles
  作者：Błażej Gierczyk、Maciej Zalas、Marcin Kaźmierczak、Jakub Grajewski、Radosław Pankiewicz、Bożena Wyrzykiewicz

  DOI：10.1002/mrc.2804

  日期：2011.10

  Three series of substituted 1,3,4-oxadiazoles were studied by (17)O NMR spectroscopy. Chemical shifts values were correlated with empirical Hammett parameters as well as calculated bond lengths and chemical shielding values.

  通过（17）O NMR光谱研究了三个系列的取代的1,3,4-恶二唑。化学位移值与经验的哈米特参数以及计算的键长和化学屏蔽值相关。
• Organic Semiconductor Material and Light-Emitting Element, Light-Emitting Device, Lighting System, and Electronic Device Using the Same
  申请人：Seo Satoshi

  公开号：US20100060155A1

  公开（公告）日：2010-03-11

  Disclosed is a novel organic semiconductor material which has a twisted quaterphenylene skeleton as a central unit and simultaneously possesses a skeleton having an electron-transporting property and a skeleton having a hole-transporting property at the terminals of the quaterphenylene skeleton. Specifically, the organic semiconductor material has a [1,1′:2′,1″:2″,1′″]quaterphenyl-4-4′″-diyl group, and one of the terminals of the [1,1′:2′,1″:2″,1′″]quaterphenyl-4-4′″-diyl group is bonded to a skeleton having an electron-transporting property such as a benzoxazole group or an oxadiazole group. A skeleton having a hole-transporting property such as diarylamino group is introduced at the other terminal. This structure allows the formation of a compound having a bipolar property, a high molecular weight, an excellent thermal stability, a large band gap, and high triplet excitation energy.

  揭示了一种新颖的有机半导体材料，其具有扭曲的四苯乙烯骨架作为中心单元，并同时在四苯乙烯骨架的末端具有具有电子传输性能的骨架和具有孔传输性能的骨架。具体而言，该有机半导体材料具有[1,1′:2′,1″:2″,1′″]四苯基-4-4′″-二基基团，其中[1,1′:2′,1″:2″,1′″]四苯基-4-4′″-二基基团的一个末端与具有电子传输性能的骨架（如苯并噁唑基团或噁二唑基团）结合。另一个末端引入了具有孔传输性能的骨架，如二芳胺基团。这种结构允许形成具有双极性、高分子量、优异热稳定性、大带隙和高三重激发能量的化合物。
• Highly efficient blue electrophosphorescent devices with a new series of host materials: polyphenylene-dendronized oxadiazole derivatives
  作者：Shiyan Chen、Xinjun Xu、Yunqi Liu、Wenfeng Qiu、Gui Yu、Xiaobo Sun、Hengjun Zhang、Ting Qi、Kun Lu、Xike Gao、Ying Liu、Daoben Zhu

  DOI：10.1039/b705515c

  日期：——

  A new series of oxadiazole derivatives TPO, PPO, MTPO, MPPO, BTPO, and BPPO have been designed and synthesized in high yields by a convenient synthetic procedure. A single crystal structure of TPO exhibited that this polyphenylene-dendronized material has a sterically crowded structure which efficiently prevents π–π stacking and endows it with good thermal stability. The photophysical properties of the materials show strong emission between 376 and 390 nm in the films. In addition, good reversible reductive waves in the cyclic voltammograms implied that these materials might have good electron transport properties. Blue electrophosphorescent devices fabricated using these materials as the host materials and iridium(III)bis[4,6-di-fluorophenyl-pyridinato-N,C2′]picolinate as the blue phosphorescent dopant emitter show very high efficiencies. A maximum luminance of 4484 cd m−2 and an external quantum efficiency of 6.20% were achieved under ambient conditions.

  一系列新的氧杂二唑衍生物TPO、PPO、MTPO、MPPO、BTPO和BPPO已经通过一种方便的合成方法设计并合成，且产率很高。TPO的单晶结构显示出该聚苯甲烯树枝状材料具有立体拥挤的结构，这有效地阻止了π–π堆积，并赋予其良好的热稳定性。材料的光物理性质显示，在薄膜中在376到390 nm之间有强烈的发射。此外，循环伏安图中良好的可逆还原波表明这些材料可能具有良好的电子传输性能。使用这些材料作为主材料，铱(III)双[4,6-二氟苯基-吡啶-N,C2']皮克林酸盐作为蓝色磷光掺杂发射体制造的蓝色电致磷光器件表现出非常高的效率。在环境条件下，达到了4484 cd m−2的最高亮度和6.20%的外量子效率。
• OXADIAZOLE DERIVATIVE, LIGHT-EMITTING ELEMENT, DISPLAY DEVICE, LIGHTING DEVICE, AND ELECTRONIC DEVICE
  申请人：NOMURA Hiroko

  公开号：US20100244669A1

  公开（公告）日：2010-09-30

  Provided is a bipolar substance having high excitation energy, in particular, high triplet-excitation energy. An oxadiazole derivative represented by General Formula (G1) below is provided In the formula, Ar represents a substituted or unsubstituted aryl group having 6 to 10 carbon atoms in a ring. R 1 represents an alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms in a ring. R 2 represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms in a ring.

  提供的是一种具有高激发能量，特别是高三重激发能量的双极性物质。下面是通用公式（G1）表示的噁二唑衍生物。在公式中，Ar代表一个具有6到10个碳原子的环中的取代或未取代芳基。R1代表一个具有1到4个碳原子的烷基或一个具有6到10个碳原子的环中的取代或未取代芳基。R2代表氢，一个具有1到4个碳原子的烷基，或一个具有6到10个碳原子的环中的取代或未取代芳基。
• [EN] FLUORENE DERIVATIVE, LIGHT-EMITTING ELEMENT, LIGHT-EMITTING DEVICE, ELECTRONIC DEVICE, AND LIGHTING DEVICE<br/>[FR] DÉRIVÉ DE FLUORÈNE, ÉLÉMENT ÉMETTEUR DE LUMIÈRE, DISPOSITIF ÉMETTEUR DE LUMIÈRE, DISPOSITIF ÉLECTRONIQUE ET DISPOSITIF D'ÉCLAIRAGE
  申请人：SEMICONDUCTOR ENERGY LAB

  公开号：WO2010137601A1

  公开（公告）日：2010-12-02

  An object is to provide a light-emitting element having high light-emission efficiency by provision of a novel fluorene derivative as represented by General Formula (G1) below. In the formula, R1 to R8 independently represent any of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group. Further, α1 to α4 independently represent any of a substituted or unsubstituted arylene group having 6 to 12 carbon atoms. Furthermore, Ar1 and Ar2 independently represent any of an aryl group having 6 to 13 carbon atoms in a ring and Ar3 represents an alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms. J, k, m, and n each independently represent 0 or 1.

  本发明的目的是通过提供如下所示的通式（G1）所代表的新型芴衍生物，提供具有高发光效率的发光元件。在该式中，R1至R8独立地表示氢原子、具有1至6个碳原子的烷基基团、取代或未取代的苯基团，或取代或未取代的联苯基团中的任何一种。此外，α1至α4独立地表示具有6至12个碳原子的取代或未取代的芳基基团中的任何一种。此外，Ar1和Ar2独立地表示环中具有6至13个碳原子的芳基基团中的任何一种，Ar3表示具有1至6个碳原子的烷基基团或具有6至12个碳原子的取代或未取代的芳基基团。J、k、m和n各自独立地表示0或1。