5-氰基苯并[b]噻吩-2-羧酸甲酯 | 146137-93-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 中文名称: 5-氰基苯并[b]噻吩-2-羧酸甲酯
• 英文名称: methyl 5-cyanobenzo[b]thiophene-2-carboxylate
• 英文别名: Methyl 5-cyano-1-benzothiophene-2-carboxylate
• CAS: 146137-93-1
• 化学式: C₁₁H₇NO₂S
• 分子量: 217.248
• InChiKey: YFASDULUSJYUSP-UHFFFAOYSA-N

物化性质

• 沸点：
  382.9±22.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  78.3
• 氢给体数：
  0
• 氢受体数：
  4

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  5-碘苯并[b]噻吩-2-羧酸甲酯	methyl 5-iodobenzo[b]thiophene-2-carboxylate	146137-90-8	C10H7IO2S	318.135
  1-苯并噻吩-5-腈	benzo[b]thiophene-5-carbonitrile	2060-63-1	C9H5NS	159.211

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  5-氰基-1-苯并噻吩-2-羧酸	5-cyanobenzo[b]thiophene-2-carboxylic acid	154650-76-7	C10H5NO2S	203.221
  2-(羟甲基)-1-苯并噻吩-5-腈	2-(hydroxymethyl)benzo[b]thiophene-5-carbonitrile	105191-15-9	C10H7NOS	189.238
  苯并[b]噻吩-5-甲腈,2-甲酰基-	2-Formylbenzothiophen-5-carbonitril	105191-42-2	C10H5NOS	187.222

反应信息

• 作为反应物：
  描述：

  5-氰基苯并[b]噻吩-2-羧酸甲酯 在 sodium tetrahydroborate 、 碳酸氢钠 、 calcium iodide 作用下， 以 四氢呋喃 为溶剂， 生成 2-(羟甲基)-1-苯并噻吩-5-腈
  参考文献：
  名称：

  Design, synthesis and structure–Activity relationships of benzoxazinone-Based factor Xa inhibitors

  摘要：

  A series of benzoxazinone derivatives was designed and synthesized as factor Xa inhibitors. We demonstrated that the naphthyl moiety in the aniline-based compounds I and 2 can be replaced with benzene-fused heterobicycles and biaryls to give factor Xa inhibitors with improved trypsin selectivity. The P4 modifications lead to monoamidines which are moderately active. The benzoxazinones 41-45 are potent against factor Xa, retain the improved trypsin selectivity of the corresponding aniline-based compounds, and show strong antithrombotic effect dose responsively. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(02)00927-7
• 作为产物：
  描述：

  对氟苯腈 在 sodium hydride 、 lithium diisopropyl amide 作用下， 反应 0.03h， 生成 5-氰基苯并[b]噻吩-2-羧酸甲酯
  参考文献：
  名称：

  氟作为芳族金属中的邻位导向基团：取代苯并[b]噻吩-2-羧酸酯的两步制备

  摘要：

  已经开发了由芳基氟化物简单地两步合成B环取代的苯并[b]噻吩-2-羧酸酯的方法。该路线涉及对氟的邻位选择性锂化，然后进行甲酰化，随后在一次操作中用硫代乙醇酸酯置换氟并进行碱诱导的闭环。

  DOI：

  10.1016/s0040-4039(00)60806-7

文献信息

• METHOD FOR PROMOTING PLANT GROWTH
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：US20150282482A1

  公开（公告）日：2015-10-08

  The present invention provides a method for promoting plant growth, which comprises treating a plant with a compound represented by the following Formula (1): provided that a method for promoting plant growth which comprises treating plants with a compound corresponding to any one of the following (1) to (8) is excluded: (1) Methyl 4-(trifluoromethyl)benzo[b]thiophene-2-carboxylate, (2) Methyl 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylate, (3) Methyl 6-(trifluoromethyl)benzo[b]thiophene-2-carboxylate, (4) Methyl 7-(trifluoromethyl)benzo[b]thiophene-2-carboxylate, (5) Ethyl 4-(trifluoromethyl)benzo[b]thiophene-2-carboxylate, (6) Ethyl 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylate, (7) Ethyl 6-(trifluoromethyl)benzo[b]thiophene-2-carboxylate, and (8) Ethyl 7-(trifluoromethyl)benzo[b]thiophene-2-carboxylate.

  本发明提供了一种促进植物生长的方法，包括用下式表示的化合物处理植物： 只要排除用与以下任一化合物相对应的化合物处理植物的促进植物生长方法：(1) 甲基4-(三氟甲基)苯并[b]噻吩-2-羧酸酯，(2) 甲基5-(三氟甲基)苯并[b]噻吩-2-羧酸酯，(3) 甲基6-(三氟甲基)苯并[b]噻吩-2-羧酸酯，(4) 甲基7-(三氟甲基)苯并[b]噻吩-2-羧酸酯，(5) 乙基4-(三氟甲基)苯并[b]噻吩-2-羧酸酯，(6) 乙基5-(三氟甲基)苯并[b]噻吩-2-羧酸酯，(7) 乙基6-(三氟甲基)苯并[b]噻吩-2-羧酸酯，以及(8) 乙基7-(三氟甲基)苯并[b]噻吩-2-羧酸酯。
• Synthesis of aryl nitriles by palladium-assisted cyanation of aryl iodides using tert-butyl isocyanide as cyano source
  作者：Xiao Jiang、Jin-Mei Wang、Ying Zhang、Zhong Chen、Yong-Ming Zhu、Shun-Jun Ji

  DOI：10.1016/j.tet.2015.04.059

  日期：2015.7

  A palladium-catalyzed synthesis of aryl nitriles by the cyanation of aryl iodides with tert-butyl isocyanide as cyano source has been developed. This novel and efficient method avoids the use of toxic cyanides. The reaction is easy-to-handle and shows good functional group compatibility.

  已经开发了通过用叔丁基异氰化物作为氰基源氰化芳基碘化物来钯催化的芳基腈的合成。这种新颖而有效的方法避免了使用有毒的氰化物。该反应易于处理并且显示出良好的官能团相容性。
• 5,6-Bicyclic glycoprotein IIb IIIa antagonists useful in inhibition of platelet aggregation
  申请人：ELI LILLY AND COMPANY

  公开号：EP0655439A3

  公开（公告）日：1997-10-08

  This invention relates to 5,6 fused ring bicyclic compounds inclusive of indoles, benzofurans, and benzothiophenes, and corresponding to the formula (I) substituted with both basic (B) and acidic (A) functionality, which are useful in inhibition of platelet aggregation.

  这项发明涉及5,6融合环双环化合物，包括吲哚、苯并呋喃和苯并噻吩，并对应于配有基本（B）和酸性（A）功能的化学式（I），这些化合物在抑制血小板聚集方面具有用途。
• Sulfonamide bridging compounds that inhibit tryptase activity
  申请人：Array Biopharma Inc.

  公开号：US06221914B1

  公开（公告）日：2001-04-24

  The present invention is directed to compounds which are capable of inhibiting the activity of tryptase. Such compounds are useful in the treatment or prevention of inflammatory disease, particularly those disease states which are mediated by mast cell activation. Also encompassed by the invention are formulations comprising the noted compounds, processes for preparing such compounds and methods for treating or preventing an inflammatory disease.

  本发明涉及一种能够抑制色氨酸蛋白酶活性的化合物。这些化合物对于治疗或预防炎症性疾病是有用的，特别是那些由肥大细胞激活介导的疾病状态。该发明还包括含有上述化合物的配方、制备这种化合物的方法以及治疗或预防炎症性疾病的方法。
• Benzo[ b ]thiophene-2-carboxamide derivatives as potent urotensin-II receptor antagonists
  作者：Chae Jo Lim、Seong Eun Woo、Su Ik Ko、Byung Ho Lee、Kwang-Seok Oh、Kyu Yang Yi

  DOI：10.1016/j.bmcl.2016.08.049

  日期：2016.10

  Members of a series of benzo[b]thiophene-2-carboxamide derivatives, possessing an N-(1-(3-bromo-4-(piperidin-4-yloxy)benzyl)piperidin-4-yl) group, were synthesized and evaluated as urotensin-II receptor antagonists. The results show that these substances have potent UT binding affinities. Observations made in a systematic SAR investigation of the effects of a variety of substituents (R(1) and R(2))

  合成了具有N-（1-（3-溴-4-（哌啶丁-4-基氧基）苄基）哌啶丁-4-基）基团的一系列苯并[b]噻吩-2-羧酰胺衍生物，并被评估为urotensin-II受体拮抗剂。结果表明，这些物质具有有效的UT结合亲和力。在系统的SAR调查中观察到的苯并[b]噻吩-2-羧酰胺部分的5和6位上的各种取代基（R（1）和R（2））对UT结合亲和力的影响导致鉴定出5-氰基类似物7f为高效UT拮抗剂，IC50值为25nM。尽管7f具有良好的代谢稳定性，但它却是CYP同工酶的有效抑制剂，并显示出不合适的PK特性。