3,4-二甲基噻吩-2,5-二羰基腈 | 155632-41-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 中文名称: 3,4-二甲基噻吩-2,5-二羰基腈
• 中文别名: 3,4-二甲基噻吩-2,5-二甲腈
• 英文名称: 2,5-Dicyano-3,4-dimethylthiophene
• 英文别名: 3,4-Dimethylthiophene-2,5-dicarbonitrile
• CAS: 155632-41-0
• 化学式: C₈H₆N₂S
• mdl: MFCD00041438
• 分子量: 162.215
• InChiKey: KJJOQVQJRGSFGU-UHFFFAOYSA-N

物化性质

• 熔点：
  122-124°C
• 沸点：
  305.5±37.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  75.8
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  6.1
• 安全说明：
  S22,S36/37
• 危险类别码：
  R20/21/22
• 海关编码：
  2934999090
• 包装等级：
  III
• 危险类别：
  6.1
• 危险品运输编号：
  UN 3276

反应信息

• 作为反应物：
  描述：

  3,4-二甲基噻吩-2,5-二羰基腈 在 溴 作用下， 以 四氯化碳 为溶剂， 反应 9.0h， 以53%的产率得到3,4-Bis(bromomethyl)-2,5-dicyanothiophene
  参考文献：
  名称：

  Synthesis of the First Thieno[3,4-c]thiophene Stabilized Only by Electronic Effects

  摘要：

  The stable, crystalline 1,3-dibromo-4,6-dicyanothieno[3,4-c]thio (3a) has been synthesized. This is the first example of a thieno[3,4-c]thiophene stabilized solely by electronic effects. The dicarbomethoxy dibromo analog 3b and the tetrabromo analog 3c were also-generated and found to be considerably less stable.

  DOI：

  10.1021/jo00087a045
• 作为产物：
  描述：

  5-氰基-3,4-二甲基噻吩-2-羧胺 在 氯化亚砜 作用下， 反应 2.5h， 以94%的产率得到3,4-二甲基噻吩-2,5-二羰基腈
  参考文献：
  名称：

  Synthesis and biological evaluation of novel benzimidazole derivatives and their binding behavior with bovine serum albumin

  摘要：

  A series of novel benzimidazole derivatives were synthesized and characterized by H-1 NMR, C-13 NMR, MS, IR and HRMS spectra. All the new compounds were screened for their antimicrobial activities in vitro by two-fold serial dilution technique. Bioactive assay manifested that the bis-benzimidazole derivative lid and its hydrochloride 13b exhibited remarkable antimicrobial activities, which were comparable or even better than the reference drugs Norfloxacin, Chloromycin and Fluconazole. The interaction evaluation of compound 11d with bovine serum albumin (BSA) by Fluorescence and UV-vis absorption spectroscopic method showed that BSA could generate fluorescent quenching under approximately human physiological conditions by the prepared benzimidazole compound lid as result of the formation of ground-state compound 11d BSA complex. The thermodynamic parameters indicated that the hydrogen bonds and van der Waals forces played major roles in the strong association of benzimidazole lid and BSA. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.07.015

文献信息

• 1,4-Hydroboration Reactions of Electron-Poor Aromatic Rings by N-Heterocyclic Carbene Boranes
  作者：Wen Dai、Steven J. Geib、Dennis P. Curran

  DOI：10.1021/jacs.0c00490

  日期：2020.4.1

  Reactions of N-heterocyclic carbene boranes (NHC-boranes) with electron poor aromatic rings under photoredox conditions provide dearomatized 3-NHC-boryl-1,5-cycohexadienes, which are formally products of 1,4-hydroboration reactions. When regioisomers are possible, the more crowded (doubly ortho-substituted) product is formed preferably or exclusively. The mechanism is thought to involve oxidation of

  N-杂环卡宾硼烷 (NHC-硼烷) 与缺电子芳环在光氧化还原条件下的反应提供脱芳构化的 3-NHC-boryl-1,5-环己二烯，它是 1,4-硼氢化反应的正式产物。当区域异构体可能时，优选或排他地形成更拥挤的（双邻位取代的）产物。该机制被认为涉及 NHC-硼烷氧化为 NHC-硼基自由基，将缺电子芳环还原为自由基阴离子，自由基与自由基阴离子偶联生成环己二烯基阴离子，最后进行区域选择性质子化。
• AROMATIC AND HETEROAROMATIC COMPOUNDS USEFUL IN TREATING IRON DISORDERS
  申请人：Cadieux Jean-Jacques

  公开号：US20100240713A1

  公开（公告）日：2010-09-23

  This invention is directed to compounds of formula (I), wherein m, formula (II), R 1 , R 2 and R 3 are as defined herein, as a stereoisomer, enantiomer, tautomer thereof or mixtures thereof; or a pharmaceutically acceptable salt, solvate or prodrug thereof, for the treatment of iron disorders. This invention is also directed to pharmaceutical compositions comprising the compounds and methods of using the compounds to treat iron disorders.

  本发明涉及式（I）的化合物，其中m、式（II）、R1、R2和R3如本文所定义，作为立体异构体、对映异构体、互变异构体或其混合物；或其药学上可接受的盐、溶剂或前药，用于治疗铁代谢紊乱。本发明还涉及包含该化合物的制药组合物以及使用该化合物治疗铁代谢紊乱的方法。
• Beye Norbert, Cava Michael P., J. Org. Chem, 59 (1994) N 8, S 2223-2226
  作者：Beye Norbert, Cava Michael P.

  DOI：——

  日期：——
• [EN] AROMATIC AND HETEROAROMATIC COMPOUNDS USEFUL IN TREATING IRON DISORDERS<br/>[FR] COMPOSÉS AROMATIQUES ET HÉTÉROAROMATIQUES UTILES DANS LE TRAITEMENT DE TROUBLES DU MÉTABOLISME DU FER
  申请人：XENON PHARMACEUTICALS INC

  公开号：WO2008151288A2

  公开（公告）日：2008-12-11

  [EN] This invention is directed to compounds of formula (I), wherein m, formula (II), R1, R2 and R3 are as defined herein, as a stereoisomer, enantiomer, tautomer thereof or mixtures thereof; or a pharmaceutically acceptable salt, solvate or prodrug thereof, for the treatment of iron disorders. This invention is also directed to pharmaceutical compositions comprising the compounds and methods of using the compounds to treat iron disorders.
  [FR] La présente invention concerne des composes de formule (I), dans laquelle m, formule (II), R1, R2 et R3 sont tels que définis dans la description, sous forme d'un stéréoisomère, énantiomère, tautomère de ceux-ci ou leurs mélanges ; ou un sel, solvate ou promédicament pharmaceutiquement acceptable de ceux-ci, pour le traitement de troubles du métabolisme du fer. L'invention concerne également des compositions pharmaceutiques comportant les composés et des procédés d'utilisation des composés pour traiter des troubles du métabolisme du fer.
• Synthesis and biological evaluation of novel benzimidazole derivatives and their binding behavior with bovine serum albumin
  作者：Shao-Lin Zhang、Guri L.V. Damu、Ling Zhang、Rong-Xia Geng、Cheng-He Zhou

  DOI：10.1016/j.ejmech.2012.07.015

  日期：2012.9

  A series of novel benzimidazole derivatives were synthesized and characterized by H-1 NMR, C-13 NMR, MS, IR and HRMS spectra. All the new compounds were screened for their antimicrobial activities in vitro by two-fold serial dilution technique. Bioactive assay manifested that the bis-benzimidazole derivative lid and its hydrochloride 13b exhibited remarkable antimicrobial activities, which were comparable or even better than the reference drugs Norfloxacin, Chloromycin and Fluconazole. The interaction evaluation of compound 11d with bovine serum albumin (BSA) by Fluorescence and UV-vis absorption spectroscopic method showed that BSA could generate fluorescent quenching under approximately human physiological conditions by the prepared benzimidazole compound lid as result of the formation of ground-state compound 11d BSA complex. The thermodynamic parameters indicated that the hydrogen bonds and van der Waals forces played major roles in the strong association of benzimidazole lid and BSA. (C) 2012 Elsevier Masson SAS. All rights reserved.

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