2,6-diamino-4-(thiophen-2-yl)-4H-thiopyran-3,5-dicarbonitrile | 127118-65-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫吡喃类
• 英文名称: 2,6-diamino-4-(thiophen-2-yl)-4H-thiopyran-3,5-dicarbonitrile
• 英文别名: 2,6-diamino-3,5-dicyano-4-(2-thienyl)-4H-thiopyran；2,6-diamino-4-(2-thienyl)-4H-thiopyran-3,5-dicarbonitrile；2,6-diamino-4-thiophen-2-yl-4H-thiopyran-3,5-dicarbonitrile
• CAS: 127118-65-4
• 化学式: C₁₁H₈N₄S₂
• mdl: MFCD00446173
• 分子量: 260.343
• InChiKey: YCDJPLGSMCQRMT-UHFFFAOYSA-N

物化性质

• 熔点：
  162-165 °C
• 沸点：
  637.8±55.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  153
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,6-diamino-4-(thiophen-2-yl)-4H-thiopyran-3,5-dicarbonitrile 在 N-甲基吗啉 作用下， 以 乙醇 为溶剂， 生成 2-amino-6-sulfanyl-4-(thiophen-2-yl)pyridine-3,5-dicarbonitrile
  参考文献：
  名称：

  Cyclization reactions of nitriles

  摘要：

  The interaction of 2-thienylidene derivatives of malononitrile and cyanothioacetamide with methylene active nitriles gives 2,6-diamino-3,5-dicyano-4-(2-thienyl)-4H-thiopyran which is smoothly recrystallized into 6-amino-3,5-dicyano-4-(2-thienyl)-2-(1H)-pyridinethione. The latter is easily alkylated at the sulfur atom by alpha-halocarbonyl compounds. This reaction was used in the synthesis of 3,6-diamino-4-(2-thienyl)thieno[2,3-b]pyridines.

  DOI：

  10.1007/bf00961252
• 作为产物：
  描述：

  2-氰基硫代乙酰胺 、 (2-噻吩亚甲基)甲烷-1,1-二甲腈 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 2,6-diamino-4-(thiophen-2-yl)-4H-thiopyran-3,5-dicarbonitrile
  参考文献：
  名称：

  Heterocycles Synthesis through Reactions of Nucleophiles with Acrylonitriles. 7. A Novel and Facile One-Step Synthesis of 4H-Thiopyrans

  摘要：

  通过一种简单的一步法合成了几种新的4H-噻吡呋。还报告了它们的结构和反应机制，并由其他合成路线进行了支持。

  DOI：

  10.1246/bcsj.62.3768

文献信息

• Multicomponent Synthesis of 4-Alkyl(Aryl, Hetaryl)-2-alkoxycarbonyl(aroyl, carbamoyl)- 3,6-diamino-5-cyanothieno[2,3-b]pyridines
  作者：I. V. Dyachenko、V. D. Dyachenko、P. V. Dorovatovskii、V. N. Khrustalev、V. G. Nenajdenko

  DOI：10.1134/s1070428018100019

  日期：2018.10

  The condensation of malononitrile with hydrogen sulfide and aldehydes in the presence of triethylamine in ethanol at room temperature afforded 4-alkyl(aryl, hetaryl)-2,6-diamino-3,5-dicyano-4H-thiopyrans. Treatment of the latter in situ with alkali in DMF, followed by addition of an alkylating agent, led to the formation of 4-alkyl(aryl, hetaryl)-2-alkoxycarbonyl(aroyl, carbamoyl)-3,6-diamino-5-cyanothieno[2

  在三乙胺的存在下，室温下丙二腈与硫化氢和醛的缩合，得到4-烷基（芳基，杂芳基）-2，6-二氨基-3，5-二氰基-4 H-硫代吡喃。后者在DMF中用碱原位处理，然后添加烷基化剂，导致形成4-烷基（芳基，杂芳基）-2-烷氧基羰基（芳酰基，氨基甲酰基）-3,6-二氨基-5-基氰基噻吩并[2,3- b ]-吡啶。
• Synthesis of 4-alkyl(aryl, hetaryl)-2-thioxo-5,6,7,8-tetrahydroquinoline-3-carbonitriles and their derivatives by cross-recyclization of 4-alkyl(aryl, hetaryl)-2,6-diamino-4H-thiopyran-3,5-dicarbonitriles with 4-(cyclohex-1-en-1-yl)-morpholine, alkyl halides, and cyclohexanone
  作者：V. D. Dyachenko、A. D. Dyachenko

  DOI：10.1134/s1070428008030172

  日期：2008.3

  Cross recyclization of 4-substituted 2,6-diamino-4H-thiopyran-3,5-dicarbonitriles with 4-(cyclohex-1-en-1-yl)morpholine, alkyl halides, and cyclohexanone gave the corresponding substituted 2-thioxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitriles, 2-alkylsulfanyl-5,6,7,8-tetrahydroquinoline-3-carbonitriles, 3-amino-5,6,7,8-tetrahydrothieno[2,3-b]quinoline-2-carboxamides, and 4-oxo-2,2-pentamethylene-1,2,3,4,7,8,9,10-octahydropyrimido[4′,5′:4,5]thieno[2,3-b]quinolines. The structure of 3-(4-bromophenyl)-2,2-pentamethylene-11-(2-thienyl)-1,2,3,4,7,8,9,10-octahydropyrimido[4′,5′:4,5]thieno[2,3-b]quinoline was proved by X-ray analysis.

  4-取代的2,6-二氨基-4H-噻吡啶-3,5-二腈与4-(环己烯-1-基)吗啉、烷基卤化物和环己酮进行交叉重环化反应，得到了相应的取代2-硫代-1,2,5,6,7,8-六氢喹啉-3-腈、2-烷基硫代-5,6,7,8-四氢喹啉-3-腈、3-氨基-5,6,7,8-四氢噻吡啶[2,3-b]喹啉-2-氨基甲酸酯，以及4-氧-2,2-戊五烯-1,2,3,4,7,8,9,10-八氢嘧啶[4′,5′:4,5]噻吡啶[2,3-b]喹啉。3-(4-溴苯基)-2,2-戊五烯-11-(2-噻吡啶基)-1,2,3,4,7,8,9,10-八氢嘧啶[4′,5′:4,5]噻吡啶[2,3-b]喹啉的结构通过X射线分析得到了证明。
• Heterocycles Synthesis through Reactions of Nucleophiles with Acrylonitriles. 7. A Novel and Facile One-Step Synthesis of 4<i>H</i>-Thiopyrans
  作者：Fathy Fahim Abdel-Latif

  DOI：10.1246/bcsj.62.3768

  日期：1989.11

  Several new 4H-thiopyrans were synthesized via a facile one-step method. Structures and reaction mechanisms are also reported and supported by another synthetic routes.

  通过一种简单的一步法合成了几种新的4H-噻吡呋。还报告了它们的结构和反应机制，并由其他合成路线进行了支持。
• Bis(4-pyridylamino)triazine-stabilized magnetite nanoparticles: preparation, characterization and application as a retrievable catalyst for the green synthesis of 4<i>H</i>-pyran, 4<i>H</i>-thiopyran and 1,4-dihydropyridine derivatives
  作者：M. A. Bodaghifard、A. Mobinikhaledi、S. Asadbegi

  DOI：10.1002/aoc.3557

  日期：2017.2

  Synthesis of bis(4‐pyridylamino)triazine stabilized on silica‐coated nano‐Fe3O4 particles, and their feasibility as a reusable heterogeneous basic catalyst are reported. The catalytic performance of this novel material was studied for the green synthesis of highly functionalized 4H‐pyran, 4H‐thiopyran and 1,4‐dihydropyridine derivatives via one‐pot multicomponent reactions. Eco‐friendly method, high

  已报道了在二氧化硅包覆的纳米Fe 3 O 4颗粒上稳定的双（4-吡啶基氨基）三嗪的合成及其作为可重复使用的非均相碱性催化剂的可行性。研究了这种新型材料的催化性能，用于绿色合成高度官能化的4 H-吡喃，4 H一锅多组分反应生成的硫代吡喃和1,4-二氢吡啶衍生物。环保的方法，所需产品的高收率和纯度，较短的反应时间以及简便的后处理程序概述了这些新方法相对于早期方法的优势。通过透射和扫描电子显微镜，X射线衍射，能量色散X射线和傅立叶变换红外光谱以及振动样品磁强分析对核-壳杂化纳米颗粒的表面和磁性进行了表征。版权所有©2016 John Wiley＆Sons，Ltd.
• INHIBITORS OF CRL4 UBIQUITIN LIGASE AND USES THEREOF
  申请人：Cornell University

  公开号：US20150196546A1

  公开（公告）日：2015-07-16

  The invention is directed to a method of treating a cancer in an animal and a method of increasing DNA repair activity in an animal. The methods comprise administering to an animal in need thereof an effective amount of a small molecule substance that interferes with the activity of CUL4A, such as a 1,3-benzoxathiol-2-one compound, a pyridine thione compound, a 2,6-diamino-4-thiopyran-3,5-dicarbonitrile compound, or a 1,2,4-triazole-3-thiol compound.

  本发明涉及一种治疗动物癌症和增加动物DNA修复活性的方法。该方法包括向需要治疗的动物中投与有效量的干扰CUL4A活性的小分子物质，比如1,3-苯并噻吩-2-酮化合物、吡啶硫酮化合物、2,6-二氨基-4-硫代吡喃-3,5-二氰基化合物或1,2,4-三唑-3-硫醇化合物。