3,5-diiodobenzonitrile 3,5-diiodobenzonitrile | 289039-52-7

• 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: 3,5-diiodobenzonitrile 3,5-diiodobenzonitrile
• 英文别名: 3,5-diiodobenzonitrile
• CAS: 289039-52-7
• 化学式: C₇H₃I₂N
• 分子量: 354.917
• InChiKey: REFGPPPOXDYZBH-UHFFFAOYSA-N

物化性质

• 沸点：
  338.1±32.0 °C(Predicted)
• 密度：
  2.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  10
• 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：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,5-diiodobenzonitrile 3,5-diiodobenzonitrile 在 盐酸 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 乙醚 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.25h， 生成 3-(2-(2-methylthiazol-4-yl)ethynyl)-5-iodobenzonitrile hydrochloride
  参考文献：
  名称：

  Potent mGluR5 antagonists: Pyridyl and thiazolyl-ethynyl-3,5-disubstituted-phenyl series

  摘要：

  We report the synthesis of four series of 3,5-disubstituted-phenyl ligands targeting the metabotropic glutamate receptor subtype 5: (2-methylthiazol-4-yl)ethynyl (1a-j,), (6-methylpyridin-2-yl)ethynyl (2a-j), (5-methylpyridin-2-yl)ethynyl (3a-j,), and (pyridin-2-yl)ethynyl (4a-j,). The compounds were evaluated for antagonism of glutamate-mediated mobilization of internal calcium in an mGluR5 in vitro assay. All compounds were found to be full antagonists and exhibited low nanomolar to subnanomolar activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.047
• 作为产物：
  描述：

  3,5-diiodobenzoyl chloride 在 ammonium hydroxide 、 氯化亚砜 作用下， 反应 18.0h， 生成 3,5-diiodobenzonitrile 3,5-diiodobenzonitrile
  参考文献：
  名称：

  Potent mGluR5 antagonists: Pyridyl and thiazolyl-ethynyl-3,5-disubstituted-phenyl series

  摘要：

  We report the synthesis of four series of 3,5-disubstituted-phenyl ligands targeting the metabotropic glutamate receptor subtype 5: (2-methylthiazol-4-yl)ethynyl (1a-j,), (6-methylpyridin-2-yl)ethynyl (2a-j), (5-methylpyridin-2-yl)ethynyl (3a-j,), and (pyridin-2-yl)ethynyl (4a-j,). The compounds were evaluated for antagonism of glutamate-mediated mobilization of internal calcium in an mGluR5 in vitro assay. All compounds were found to be full antagonists and exhibited low nanomolar to subnanomolar activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.047

文献信息

• IODINE(III)-MEDIATED RADIOFLUORINATION
  申请人：The General Hospital Corporation

  公开号：US20150252007A1

  公开（公告）日：2015-09-10

  A process for fluorination of aromatic compounds employing iodonium ylides and applicable to radiofluorination using 18 F is described. Processes, intermediates, reagents and radiolabelled compounds are described.

  描述了一种使用碘化亚胺基和适用于使用18F进行放射性氟化的芳香化合物氟化的过程。描述了过程、中间体、试剂和放射性标记化合物。
• ORGANIC ELECTROLUMINESCENT MATERIALS AND DEVICES
  申请人：Universal Display Corporation

  公开号：US20170018721A1

  公开（公告）日：2017-01-19

  A compound having a structure of Formula I: is provided. In the structure of Formula I, each one of X 1 to X 16 is independently CR X or N; each R X and R are independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, carbazole, azacarbazole, dibenzofuran, dibenzothiophene, dibenzoselenophene, azadibenzofuran, azadibenzothiophene, azadibenzoselenophene, triphenylene, azatriphenylene, and combinations thereof; and any adjacent R X can join to form fused or unfused rings. Formulations and devices, such as an OLEDs, that include the compound containing a structure of Formula I are also described.

  提供了具有Formula I结构的化合物。在Formula I结构中，X1到X16中的每一个都独立地是CRX或N；每个RX和R都独立地从氢、氘、卤素、烷基、环烷基、杂原子烷基、芳基烷基、烷氧基、芳氧基、氨基、硅烷基、烯基、环烯基、杂原子烯基、炔基、芳基、杂原子芳基、酰基、羰基、羧酸、酯、腈、异腈、硫基、亚硫基、砜基、膦基、咔唑、氮杂咔唑、二苯呋喃、二苯硫喹啉、二苯硒喹啉、氮杂二苯呋喃、氮杂二苯硫喹啉、氮杂二苯硒喹啉、三苯基、氮杂三苯基等组成的群中选择；任何相邻的RX都可以连接形成融合或非融合环。还描述了包含具有Formula I结构的化合物的配方和器件，例如OLEDs。
• Syntheses of mGluR5 PET radioligands through the radiofluorination of diaryliodonium tosylates
  作者：Sanjay Telu、Joong-Hyun Chun、Fabrice G. Siméon、Shuiyu Lu、Victor W. Pike

  DOI：10.1039/c1ob05555k

  日期：——

  3-Fluoro-1-((thiazol-4-yl)ethynyl)benzenes constitute an important class of high-affinity metabotropic glutamate subtype 5 receptor (mGluR5) ligands, some of which have been labeled with fluorine-18 (t1/2 = 109.7 min), to provide radioligands for molecular imaging of brain mGluR5 in living animal and human subjects with positron emission tomography (PET). Labeling in the 3-fluoro position of such ligands can be achieved through aromatic nucleophilic substitution of a halide leaving group with [18F]fluoride ion when a weakly activating m-nitrile group is present, but is generally very low yielding (<8%). Here we used a microfluidic reaction platform to show that greatly enhanced (up to 6-fold) radiochemical yields can be achieved from suitably synthesized diaryliodonium tosylate precursors. The presence of a m-nitrile or other activating group is not required. Similar conditions were adopted in a more conventional automated radiochemistry platform having a single-pot reactor, to produce mGluR5 radioligands with useful radioactivities for PET imaging.

  3-氟-1-((噻唑-4-基)乙炔基)苯系物是一类重要的高亲和性代谢谷氨酸亚型 5 受体（mGluR5）配体，其中一些已用氟-18（t1/2 = 109.7 分钟）标记，为正电子发射断层扫描（PET）对活体动物和人体脑部 mGluR5 进行分子成像提供了放射性配体。当存在弱活化间腈基团时，可通过芳香族亲核取代卤化物离去基团与[18F]氟离子来实现此类配体 3-氟位置的标记，但通常产率很低（<8%）。在这里，我们利用微流体反应平台证明，通过适当合成二芳碘对甲苯磺酸盐前体，可大大提高放射化学产率（高达 6 倍）。无需存在间腈或其他活化基团。在具有单锅反应器的更传统的自动化放射化学平台中也采用了类似的条件，以生产具有 PET 成像有用放射性活性的 mGluR5 放射性配体。
• Water-soluble <i>meta</i> -poly(phenylene ethynylene) oligomers with stable helical secondary structure
  作者：Ha H. Nguyen、James H. McAliley、David A. Bruce

  DOI：10.1002/pola.25976

  日期：2012.5.15

  Two novel water‐soluble meta‐poly(phenylene ethynylene) (mPPE) copolymers were synthesized and characterized, each contained ester and amine functional groups attached to exohelix positions on the phenylene rings and one contained methoxy endohelix functional groups. Secondary structure formation was investigated for these materials in aqueous solutions using ultraviolet and fluorescence spectroscopy

  合成并表征了两种新型的水溶性间-聚（亚苯基乙炔）（mPPE）共聚物，每种共聚物均包含与亚苯基环上exohelix位置相连的酯和胺官能团，而另一种则含有甲氧基内螺旋功能组。使用紫外线和荧光光谱法研究了这些材料在水溶液中的二级结构形成。另外，报道了mPPE及其受保护的胺前体在其他质子和非质子溶剂中的折叠行为。结果表明，两种mPPE都能在水中形成稳定的螺旋结构，而只有未甲氧基化的聚合物在乙腈和几种醇中显示出螺旋结构。©2012 Wiley Periodicals，Inc. J Polym Sci A部分：Polym Chem，2012年
• Iodine(III)-mediated radiofluorination
  申请人：The General Hospital Corporation

  公开号：US09434699B2

  公开（公告）日：2016-09-06

  A process for fluorination of aromatic compounds employing iodonium ylides and applicable to radiofluorination using 18F is described. Processes, intermediates, reagents and radiolabelled compounds are described.

  本文描述了一种利用碘鎓亚胺进行芳香族化合物氟化的过程，并适用于使用18F进行放射性氟标记。描述了过程、中间体、试剂和放射性标记化合物。