3-iodoselenophene | 18168-61-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 3-iodoselenophene
• 英文别名: 3-iodo-selenophene；3-Iod-selenophen；3-Iodoselenophen；3-Jod-selenophen；3-Iodselenophen；Selenophene, 3-iodo-
• CAS: 18168-61-1
• 化学式: C₄H₃ISe
• 分子量: 256.932
• InChiKey: GAAVLFWNOZQEHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.35
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3-iodoselenophene 、 正辛基镁溴盐 在 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) 作用下， 以62%的产率得到octyl-3 selenophene
  参考文献：
  名称：

  通过非缔合催化剂形成具有变化序列的全共轭ABC-嵌段共聚物

  摘要：

  该手稿由两部分组成，着重于增强对共轭聚合物聚合的控制。在第一部分中，展示了使用Pd（Ruphos）作为催化剂体系的聚硒烯聚合反应的受控链增长特性。接下来，使用该催化剂以所有可能的顺序合成全共轭噻吩-芴-硒烯三嵌段共聚物。随后，使用GPC色谱和1 H NMR，UV-vis和荧光测量评估了这些高级结构的性质。进行DFT计算以解释聚合过程中单体序列的异常独立性，这在传统上通常会在共轭聚合物的其他链增长方案中观察到。

  DOI：

  10.1021/ma500610p
• 作为产物：
  描述：

  四碘硒吩 在 水 、 溶剂黄146 、 锌 作用下， 反应 2.5h， 以3.1 g的产率得到3-iodoselenophene
  参考文献：
  名称：

  通过硒酚-噻吩共聚控制共轭聚合物的相分离和光学性能

  摘要：

  合成并研究了硒酚-噻吩嵌段共聚物。这些新型嵌段共聚物的性质不同于由具有相似组成的相同单体制备的统计共聚物的性质。具体而言，嵌段共聚物在固态下表现出广泛的红移吸光度特征和相分离域。扫描透射电子显微镜和地形元素映射证实这些域富含硒酚或噻吩，表明不同杂环的块优先在固态下相互结合。鉴于重复单元之间的化学相似性，这种偏好是令人惊讶的。总体结果证明了由元素差异控制的相分离。由于这种相分离，

  DOI：

  10.1021/ja103191u

文献信息

• Indole-3-Acetic Acids and Hetero Analogues by One Pot Synthesis including Heck Cyclisation
  作者：David Wensbo、Ulf Annby、Salo Gronowitz

  DOI：10.1016/0040-4020(95)00601-4

  日期：1995.9

  Bz-substituted indole-3-acetic acid ethyl esters (14e-g) and heteroanalogues, i.e. thienopyrroles (14a, c) and selenolopyrrole (14d), were prepared starting from N-BOC protected o-iodo aryl amines. Allylation with ethyl 4-bromocrolonate, followed by palladium-catalysed ring closure in a one pot reaction, yielded N-BOC protected indoles (13e-g), thienopyrroles (13a-c), and selenolopyrrole (13d). The

  从N-BOC保护的邻碘碘芳基胺开始，制备Bz取代的吲哚-3-乙酸乙酯（14e-g）和杂类似物，即噻吩并吡咯（14a，c）和硒代吡咯（14d）。与4-溴丁烯酸乙酯进行烯丙基化，然后在一个锅中进行钯催化的闭环反应，得到N-BOC保护的吲哚（13e-g），噻吩并吡咯（13a-c）和硒代吡咯（13d）。吸附在二氧化硅上后，BOC基团很容易被热除去。类似地制备了氧噻吩并吡咯（11a-c）。
• Synthesis, Structure, and Antiproliferative Activity of Selenophenfurin, an Inosine 5‘-Monophosphate Dehydrogenase Inhibitor Analogue of Selenazofurin
  作者：Palmarisa Franchetti、Loredana Cappellacci、Ghassan Abu Sheikha、Hiremagalur N. Jayaram、Vivek V. Gurudutt、Thaw Sint、Bryan P. Schneider、William D. Jones、Barry M. Goldstein、Graziella Perra、Antonella De Montis、Anna Giulia Loi、Paolo La Colla、Mario Grifantini

  DOI：10.1021/jm960864o

  日期：1997.5.1

  The synthesis and biological activity of selenophenfurin (5-beta-D-ribofuranosylselenophene-3-carboxamide, 1), the selenophene analogue of selenazofurin, are described. Glycosylation of ethyl selenophene-3-carboxylate (6) under stannic chloride-catalyzed conditions gave 2- and 5-glycosylated regioisomers, as a mixture of alpha- and beta-anomers, and the beta-2,5-diglycosylated derivative. Deprotected ethyl 5-beta-D-ribofuranosylselenophene-3-carboxylate (12 beta) was converted into selenophenfurin by ammonolysis. The structure of 12 beta was determined by H-1- and C-13-NMR, crystallographic, and computational studies. Selenophenfurin proved to be antiproliferative against a number of leukemia, lymphoma, and solid tumor cell lines at concentrations similar to those of selenazofurin but was more potent than the thiophene and thiazole analogues thiophenfurin and tiazofurin. Incubation of K562 cells with selenophenfurin resulted in inhibition of IMP dehydrogenase (IMPDH) (76%) and an increase in IMP pools (14.5-fold) with a concurrent decrease in GTP levels (58%). The results obtained confirm the hypothesis that the presence of heteroatoms such as S or Se in the heterocycle in position 2 with respect to the glycosidic bond is essential for both cytotoxicity and IMP dehydrogenase inhibitory activity in this type of C-nucleosides.
• Synthesis of 2,3-Dihydroselenophene and Selenophene Derivatives by Electrophilic Cyclization of Homopropargyl Selenides
  作者：Ricardo F. Schumacher、Alisson R. Rosário、Ana Cristina G. Souza、Paulo H. Menezes、Gilson Zeni

  DOI：10.1021/ol1003753

  日期：2010.5.7

  The synthesis of several highly functionalized 2,3-dihydroselenophenes from homopropargyl selenides via electrophilic cyclization is described. Electrophiles such as 12, ICI, and PhSeBr were used in a simple process employing CH2Cl2 as solvent at room temperature, which gave the cyclized products in high yields. 4-lodo-2,3-dihydroselenophenes obtained by this methodology were submitted to a dehydrogenation reaction using 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) to give 3-iodoselenophenes. 4-lodo-5-phenyl-2,3-dihydroselenophene was also submitted to the thiol copper-catalyzed and Heck-type reactions giving the desired products under mild reaction conditions.
• Conjugated Polymers with Switchable Carrier Polarity
  作者：Colin R. Bridges、Chang Guo、Han Yan、Mark B. Miltenburg、Pengfei Li、Yuning Li、Dwight S. Seferos

  DOI：10.1021/acs.macromol.5b01225

  日期：2015.8.25

  Stimuli responsive polymers can change their properties as a result of their environment. Factors such as temperature, light, pH, or solvent can all trigger a polymer response. We present conjugated polymers with switchable carrier polarity, accomplished using a functional group that can be converted from electron donating to electron withdrawing. The polymers presented herein are polyselenophenes containing alpha-ketal side-chains. The alpha-ketal side-chains can be converted to electron withdrawing alpha-ketone side-chains postpolymerization. Since the starting monomer is relatively electron-rich, it can be polymerized using chain growth methods. Switching the electron donating ability of the side chain postpolymerization is an effective way to synthesize electron-deficient conjugated polymers from electron-rich monomers. Whereas the alpha-ketal polymer has optoelectronic properties that are consistent with other electron-rich (p-type) polymers, the alpha-keto polymer features a broad red optical-absorption, narrow HOMO-LUMO gap (similar to 1.5 eV), low-lying HOMO and LUMO levels, and ambipolar charge transport properties. We support these observations using density functional theory calculations.
• Controlling Phase Separation and Optical Properties in Conjugated Polymers through Selenophene−Thiophene Copolymerization
  作者：Jon Hollinger、Ashlee A. Jahnke、Neil Coombs、Dwight S. Seferos

  DOI：10.1021/ja103191u

  日期：2010.6.30

  Selenophene-thiophene block copolymers were synthesized and studied. The properties of these novel block copolymers are distinct from those of statistical copolymers prepared from the same monomers with a similar composition. Specifically, the block copolymers exhibit broad and red-shifted absorbance features and phase-separated domains in the solid state. Scanning transmission electron microscopy

  合成并研究了硒酚-噻吩嵌段共聚物。这些新型嵌段共聚物的性质不同于由具有相似组成的相同单体制备的统计共聚物的性质。具体而言，嵌段共聚物在固态下表现出广泛的红移吸光度特征和相分离域。扫描透射电子显微镜和地形元素映射证实这些域富含硒酚或噻吩，表明不同杂环的块优先在固态下相互结合。鉴于重复单元之间的化学相似性，这种偏好是令人惊讶的。总体结果证明了由元素差异控制的相分离。由于这种相分离，

表征谱图