4-amino-5-benzoyl-2-methylsulfanylthiophene-3-carbonitrile | 116171-03-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-amino-5-benzoyl-2-methylsulfanylthiophene-3-carbonitrile
• 英文别名: 4-amino-5-benzoyl-2-methylthio-thiophen-3-carbonitrile；4-amino-5-benzoyl-2-methylsulfanyl-3-thienyl cyanide；3-Thiophenecarbonitrile, 4-amino-5-benzoyl-2-(methylthio)-
• CAS: 116171-03-0
• 化学式: C₁₃H₁₀N₂OS₂
• 分子量: 274.367
• InChiKey: JZBHTUZPSRFSMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-amino-5-benzoyl-2-methylsulfanylthiophene-3-carbonitrile 在 双氧水 、 溶剂黄146 作用下， 反应 336.0h， 生成 4-amino-5-benzoyl-2-methylsulfonyl-3-thiophene-carbonitril
  参考文献：
  名称：

  3-Amino-5-phenoxythiophenes:  Syntheses and Structure−Function Studies of a Novel Class of Inhibitors of Cellular l-Triiodothyronine Uptake

  摘要：

  A series of substituted 3-amino-5-phenoxythiophenes was synthesized starting from malodinitrile and carbon disulfide. The resulting dicyanoketenedithiolate reacts via Thorpe-Dieckmann cyclization with halogen methanes bearing electron-withdrawing groups to give thiophene-2-thiolates, which can be transformed into 3-amino-5-(methylsulfonyl)thiophene-4-carbonitriles. Replacement of the methylsulfonyl groups by substituted phenolates provides the substituted 3-amino-5-phenoxythiophenes. Some of the derivatives show a considerable inhibitory potency for the L-T-3 uptake in inhibition studies on human HepG2 hepatoma cells with maximum values of about 60% at a dose of 10(-5) M for the most potent 2-benzoyl derivatives. The structure of the phenoxythiophenes fits well into a general concept derived for other classes of L-T-3 uptake inhibitors, which postulates an angular and perpendicular orientation of the ring systems in these compounds as a prerequisite for an inhibitory potency. Docking studies for the phenoxythiophenes with transthyretin as a receptor model show their preferred attack at the L-T-4/L-T-3 binding channel.

  DOI：

  10.1021/jm980288r
• 作为产物：
  描述：

  potassium (2,2-dicyano-1-methylsulfanylethen-1-yl)thiolate 、 2-溴苯乙酮 在 溶剂黄146 作用下， 以 二甲基亚砜 为溶剂， 反应 0.5h， 以63%的产率得到4-amino-5-benzoyl-2-methylsulfanylthiophene-3-carbonitrile
  参考文献：
  名称：

  通过THORPE-ZIEGLER环化进行杂缩噻吩和噻唑

  摘要：

  描述了新颖的噻吩并吡啶酮，噻唑并吡啶酮，噻唑并吡啶以及氨基和二氨基二酮基吡啶的合成。同时证明，在这些化合物和相关的3-氨基噻吩中，可以用吗啉代基团代替甲硫基。使用1 H-，13 C-NMR，IR和元素分析对结构进行表征。

  DOI：

  10.1002/jhet.5570450419

文献信息

• A Convenient Synthesis of 2,3,4,5-Functionalised Thieno[2,3-<i>b</i>]thiophenes
  作者：Gilbert Kirsch、Geoffroy Sommen、Alain Comel

  DOI：10.1055/s-2003-38080

  日期：——

  A two steps simple synthesis of 2,3,4,5-functionalised thieno[2,3-b]thiophenes 2-6 from ketene dimethylthioacetals is described.

  描述了从乙烯酮二甲基硫缩醛中两步简单合成 2,3,4,5-功能化的噻吩并[2,3-b]噻吩 2-6。
• Parallel synthesis of 2,4,5-trisubstituted thiophene-3-carbonitrile derivatives on traceless solid support
  作者：Suyoun Lee、Doohyun Lee、Kyung-Sik Song、Kwang-Hyeon Liu、Young-Dae Gong、Taeho Lee

  DOI：10.1016/j.tet.2014.10.030

  日期：2014.12

  traceless strategy. The initial synthesis utilized the Thorpe–Ziegler type cyclization of α-haloketone and polymer-supported 2,2-dicyanoethene-1,1-bis(thiolate), which was derived from the Merrifield resin. The resulting thiophene resin was introduced to one substitution by N-arylation. After oxidation of sulfides to sulfones in the thiophene resins for subsequent cleavage, nucleophilic desulfonative

  开发了2,4,5-三取代噻吩-3-腈衍生物的平行固相合成方法。聚合物支持的合成路线是使用硫化物接头通过无痕策略进行的。最初的合成方法是使用α-卤代酮的Thorpe–Ziegler型环化反应和由Merrifield树脂衍生的聚合物负载的2,2-二氰乙烯-1,1-双（硫醇盐）。通过N-芳基化将所得的噻吩树脂引入一个取代基。在噻吩树脂中将硫化物氧化为砜以进行后续裂解后，用胺和硫醇进行亲核脱硫取代可提供所需的噻吩-3-腈衍生物，且总收率良好。
• Palladium-catalyzed, unsymmetrical homocoupling of thiophenes via carbon–sulfur bond activation: a new avenue to homocoupling reactions
  作者：Amir Hossein Vahabi、Abdolali Alizadeh、Hamid Reza Khavasi、Ayoob Bazgir

  DOI：10.1039/c7ob01923h

  日期：——

  carbonyl group in amino thiophene offers a new class of synthetic protocols for C–N cross-coupling with arylboronic acids. The bidentate N,O-chelation provides a series of advantages such as copper-catalyzed, ligand- and base-free under open-flask conditions. Interestingly, the combination of the C–N cross-coupling/homocoupling reactions in a domino fashion led to the bithiophene adducts featuring

  描述了通过空前的均偶联反应，Pd催化的，CN定向的2,4'-联噻吩的不对称合成。NH 2 / CN / SMe布置中断了例程。通过结合底物的亲电和亲核基序，噻吩中官能团的协同性能将为金属催化均偶联反应领域开辟新的视野。此外，发现氨基噻吩中羰基的α-螯合作用为C–N与芳基硼酸的交叉偶联提供了新的一类合成方法。二齿N，O螯合提供了一系列优势，例如在开瓶条件下铜催化，无配体和无碱。有趣的是，C-N交叉偶联/均偶联反应以多米诺骨牌的方式相结合，导致联噻吩加合物的特征是氮在两个噻吩单元之间桥接了C（Ar）-N键断裂。
• Highly mild approach towards synthesis of tetrasubstituted thiophenes by an organic salt afforded by cyclic thioureas and ketene dithioacetals
  作者：Abdolali Alizadeh、Amir Hossein Vahabi、Ayoob Bazgir、Hamid Reza Khavasi、Zhe Zhu、Seik Weng Ng

  DOI：10.1039/c5ra15544d

  日期：——

  An organic salt generated by cyclic thioureas and 2-di(methylsulfanyl)methylenemalononitrile in reaction with primary and secondary α-haloketones leads to tetrasubstituted thiophenes without using additional base or catalyst at room temperature.

  由环状硫脲和2-二(甲基硫基)亚甲基马来酰亚氰与一次和二次α-卤代酮反应生成的有机盐，在室温下不使用额外的碱或催化剂就能得到四取代噻吩。
• Csp3–N bond formation in aminothiophenes by 1,1-dibromo isocyanide: the unexpected 1,5-binucleophilicity of substrates
  作者：Amir Hossein Vahabi、Abdolali Alizadeh、Ayoob Bazgir

  DOI：10.1007/s13738-017-1195-9

  日期：2017.12

  linked to acetyl on the efficiency of the reaction. Also, the potential of isocyanide dibromide for the synthesis of cyclic guanidine is evaluated. Graphical AbstractAn efficient, useful and general procedure for the synthesis of 5-aroyl-4-cyclohexylamino-2-methylsulfanyl-3-thienyl cyanide via one-pot three-component reaction of 5-acetyl-4-amino-2-methylsulfanyl-3-carbonitrile, cyclohexylisocyanide and

  摘要所述Ñ -cyclohexylcarbonimidoyl二溴化物原位，通过在反应cyclohexylisocyanide和溴与几个停用的5-乙酰基-4-氨基-2-甲硫基-3-甲腈生成，显示为经由CSP环己变压器到基板3在室温下不使用任何碱或催化剂的情况下形成–N键。当前的转型提出了三项主要创新。首先，关于芳族胺的选择性单烷基化，所进行的条件是前所未有的。第二，在基于异氰化物的反应领域中，异氰酸酯首次用作烷基转移剂。第三，这是将氨基噻吩与仲烷基偶联的第一个例子。有趣的是，该方案伴随着高产率和选择性，短反应时间，易于纯化。通过这项研究，我们研究了与乙酰基连接的取代基对反应效率的电子影响。此外，评估了异氰酸二溴化物在合成环胍中的潜力。 图形概要通过5-乙酰基-4-氨基-2-甲基硫基-3-一锅三组分反应合成5-芳酰基-4-环己基氨基-2-甲基硫基-3-噻吩氰化物的有效，通用的方法已经描述了室温