2-[(2,2,2-trifluoroacetyl)amino]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide | 300852-92-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2-[(2,2,2-trifluoroacetyl)amino]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide
• 英文别名: 2-(2,2,2-Trifluoroacetamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide；2-[(2,2,2-trifluoroacetyl)amino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide
• CAS: 300852-92-0
• 化学式: C₁₁H₁₁F₃N₂O₂S
• mdl: MFCD00432942
• 分子量: 292.282
• InChiKey: NDQPBHPGVVCDRS-UHFFFAOYSA-N

物化性质

• 沸点：
  379.4±42.0 °C(Predicted)
• 密度：
  1.507±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  100
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[(2,2,2-trifluoroacetyl)amino]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide 在 N-氨基羟胺 、 三氯氧磷 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 7.17h， 生成 benzaldehyde (E)-2-[2-(trifluoromethyl)-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4-yl]hydrazone
  参考文献：
  名称：

  Synthesis and Biological Activity of New Fluorinated Thieno[2,3-d]pyrimidinyl Hydrazone Derivatives

  摘要：

  通过三氟乙酰化、环化、氯化、肼取代和缩合反应等五个步骤合成了一系列含有腙亚结构的氟化噻吩并[2,3-d]嘧啶新衍生物。红外光谱、核磁共振、电离质谱、元素分析和单晶 X 射线衍射证实了这些新合成化合物的结构。初步生物测定结果表明，一些标题化合物在 50 μgmL-1 浓度下对氧孢镰刀菌（Fusarium oxysporium f.sp.vasinfectum ）具有较好的杀菌活性，尤其是化合物 6b 的抑菌率达到 90% 以上。

  DOI：

  10.2174/1570178611666140207220959
• 作为产物：
  描述：

  环己酮 在 吗啉 、 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 aluminum oxide 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 1.5h， 生成 2-[(2,2,2-trifluoroacetyl)amino]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide
  参考文献：
  名称：

  Synthesis and Biological Activity of New Fluorinated Thieno[2,3-d]pyrimidinyl Hydrazone Derivatives

  摘要：

  通过三氟乙酰化、环化、氯化、肼取代和缩合反应等五个步骤合成了一系列含有腙亚结构的氟化噻吩并[2,3-d]嘧啶新衍生物。红外光谱、核磁共振、电离质谱、元素分析和单晶 X 射线衍射证实了这些新合成化合物的结构。初步生物测定结果表明，一些标题化合物在 50 μgmL-1 浓度下对氧孢镰刀菌（Fusarium oxysporium f.sp.vasinfectum ）具有较好的杀菌活性，尤其是化合物 6b 的抑菌率达到 90% 以上。

  DOI：

  10.2174/1570178611666140207220959

文献信息

• Heterobicyclic Compounds as Pharmaceutically Active Agents
  申请人：Koul Anil

  公开号：US20070275962A1

  公开（公告）日：2007-11-29

  Described are heterobicyclic compounds such as 4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid amides, 4,7-dihydro-5H-thieno[2,3-c]thiopyran 3-carboxylic acid amides, 4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid amides, or benzo[b]thiophene-3-carboxylic acid amides and pharmaceutically acceptable salts thereof, the use of these derivatives for the prophylaxis and/or treatment of various diseases such as infectious diseases, including mycobacteriainduced infections and opportunistic diseases, prion diseases, immunological diseases, autoimmune diseases, bipolar and clinical disorders, cardiovascular diseases, cell proliferative diseases, diabetes, inflammation, transplant rejections, erectile dysfunction, neurodegenerative diseases and stroke, as well as compositions containing at least one heterobicyclic compound and/or pharmaceutically acceptable salts thereof. Furthermore, reaction procedures for the synthesis of the heterobicyclic compound are disclosed.

  本文介绍了异杂双环化合物，例如4,5,6,7-四氢苯并[b]噻吩-3-羧酸酰胺，4,7-二氢-5H-噻吩[2,3-c]硫杂吡喃-3-羧酸酰胺，4,7-二氢-5H-噻吩[2,3-c]吡喃-3-羧酸酰胺，或苯并[b]噻吩-3-羧酸酰胺及其药学上可接受的盐。这些衍生物的用途包括预防和/或治疗各种疾病，如传染性疾病，包括分支杆菌感染和机会性疾病，朊病，免疫性疾病，自身免疫性疾病，双相和临床障碍，心血管疾病，细胞增殖性疾病，糖尿病，炎症，移植排斥，勃起功能障碍，神经退行性疾病和中风，以及含有至少一种异杂双环化合物和/或药学上可接受的盐的组合物。此外，还公开了合成异杂双环化合物的反应程序。
• HETEROBICYCLIC COMPOUNDS AS PHARMACEUTICALLY ACTIVE AGENTS
  申请人：GPC Biotech AG

  公开号：EP1670804A2

  公开（公告）日：2006-06-21
• [EN] HETEROBICYCLIC COMPOUNDS AS PHARMACEUTICALLY ACTIVE AGENTS<br/>[FR] COMPOSES HETEROBICYCLIQUES EN TANT QU'AGENTS ACTIFS AU NIVEAU PHARMACEUTIQUE
  申请人：AXXIMA PHARMACEUTICALS AG

  公开号：WO2005023818A2

  公开（公告）日：2005-03-17

  Described are heterobicyclic compounds such as 4,5,6,7-tetrahydro­benzo[b]thiophene-3-carboxylic acid amides, 4,7-dihydro-5H-thieno[2,3-c]thiopyran­ 3-carboxylic acid amides, 4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid amides, or benzo[b]thiophene-3-carboxylic acid amides and pharmaceutically acceptable salts thereof, the use of these derivatives for the prophylaxis and/or treatment of various diseases such as infectious diseases, including mycobacteria­induced infections and opportunistic diseases, prion diseases, immunological diseases, autoimmune diseases, bipolar and clinical disorders, cardiovascular diseases, cell proliferative diseases, diabetes, inflammation, transplant rejections, erectile dysfunction, neurodegenerative diseases and stroke, as well as compositions containing at least one heterobicyclic compound and/or pharmaceutically acceptable salts thereof. Furthermore, reaction procedures for the synthesis of the heterobicyclic compound are disclosed.
• Synthesis and Biological Activity of New Fluorinated Thieno[2,3-d]pyrimidinyl Hydrazone Derivatives
  作者：Xin-Jian Song、Ping Yang、Dai-Fu Wang、Zhi-Dou Tan

  DOI：10.2174/1570178611666140207220959

  日期：2014.4

  A series of new fluorinated thieno[2,3-d]pyrimidine derivatives containing hydrazone substructure was synthesized by a five-step procedure, including trifluoroacetylation, cyclization, chlorination, substitution by hydrazine, and condensation reaction. The structures of these newly synthesized compounds were confirmed by IR, NMR, EI-MS, elemental analysis and single-crystal X-ray diffraction. The preliminary bioassay result showed that some title compounds exhibited relatively good fungicidal activity against Fusarium oxysporium f.sp.vasinfectum at the concentration of 50 μgmL-1, especially the inhibition rate of compound 6b reached above 90%.

  通过三氟乙酰化、环化、氯化、肼取代和缩合反应等五个步骤合成了一系列含有腙亚结构的氟化噻吩并[2,3-d]嘧啶新衍生物。红外光谱、核磁共振、电离质谱、元素分析和单晶 X 射线衍射证实了这些新合成化合物的结构。初步生物测定结果表明，一些标题化合物在 50 μgmL-1 浓度下对氧孢镰刀菌（Fusarium oxysporium f.sp.vasinfectum ）具有较好的杀菌活性，尤其是化合物 6b 的抑菌率达到 90% 以上。