N,N,3-trimethylthiophene-2-carboxamide | 30717-56-7

• 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: N,N,3-trimethylthiophene-2-carboxamide
• CAS: 30717-56-7
• 化学式: C₈H₁₁NOS
• mdl: MFCD11726119
• 分子量: 169.247
• InChiKey: WMXONGPBIYYCSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.375
• 拓扑面积：
  48.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-甲基噻吩-2-羧酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 27.17h， 生成 N,N,3-trimethylthiophene-2-carboxamide
  参考文献：
  名称：

  Pd（II）催化的γ-C（sp 3）–H键的芳基化和分子内酰胺化：在芳基杂芳基甲烷和吡咯烷酮环环呋喃/噻吩骨架上的途中

  摘要：

  我们报告了P​​d（II）催化的，双齿指导基团（BDG）辅助的芳基化和连续的芳基化/γ-C（sp 3）–H键的芳基化。Pd（II）催化的BDG辅助羧酸的C–H活化和功能化，羧酸的β-C（sp 3）–H键，但是仅有少数报道涉及BDG指导的功能化-C（sp 3）–H键的数量。各种3-甲基噻吩/呋喃-2-羧酰胺（1a – e）衍生自其相应的羧酸和二齿导向基团。然后将这些化合物用作底物以研究γ-C（sp 3）– H键。γ-C（sp 3）-H芳基化反应是由这些化合物与芳基碘化物在Pd（II）催化下反应的，反应时间为4-24小时（少数反应需要36或48小时）。值得注意的是，这些反应导致了各种非对称二芳基甲烷的支架，例如噻吩/呋喃类arylheteroarylmethanes（建设3 - 6）。将反应时间延长至48–70 h会导致连续的γ-C（sp 3）–H芳基化/分子内酰胺化，以及C–C和C–N键的构

  DOI：

  10.1021/acs.joc.7b00582

文献信息

• Novel cyclic compound having 4-pyridylalkylthio group having substituted or unsubstituted amino group introduced therein
  申请人：Honda Takahiro

  公开号：US20070149574A1

  公开（公告）日：2007-06-28

  A novel cyclic compound having a 4-pyridylalkylthio group having an (un)substituted amino group introduced therein or a salt thereof. They are useful as a medicine. The cyclic compound is a compound represented by the following formula (1), which is useful for the treatment of diseases in which angiogenesis participates. In the following formula (1), ring A represents a benzene ring or a 5- or 6-membered aromatic heterocycle optionally fused with a cycloalkane ring; B represents alkylene; R 1 and R 2 each represents H, (substituted) aryl, (substituted) heterocyclic group, etc.; R 3 and R 4 each represents H, (substituted) alkyl, (substituted) cycloalkyl, -Z-R 5 , etc.; R 5 represents (substituted) alkyl, (substituted) aryl, (substituted) heterocyclic group, etc.; X and Y each represents H, etc.; Z represents —CO—, —COO—, —CONR 6 —, —SO 2 —, etc.; R 6 represents H, etc.; p is 0, 1, or 2; and q is 0 or 1.

  一种具有4-吡啶基烷基硫基团的新型环状化合物，其中引入了（未）取代氨基或其盐。它们可用作药物。环状化合物是由以下式（1）表示的化合物，可用于治疗参与血管生成的疾病。在下式（1）中，环A表示苯环或5-或6-成员芳香杂环，可选择地与环烷环融合；B表示烷基；R1和R2各表示H，（取代）芳基，（取代）杂环基等；R3和R4各表示H，（取代）烷基，（取代）环烷基，-Z-R5等；R5表示（取代）烷基，（取代）芳基，（取代）杂环基等；X和Y各表示H等；Z表示-CO-，-COO-，-CONR6-，-SO2-等；R6表示H等；p为0、1或2；q为0或1。
• Novel Cyclic Compound Having Pyrimidinylalkylthio Group
  申请人：Tajima Hisashi

  公开号：US20090291951A1

  公开（公告）日：2009-11-26

  The present invention has its object to study synthesis of novel cyclic compounds having a pyrimidinylalkylthio group and to find pharmacological actions of the compounds. According to the present invention, a compound represented by the formula (1) or a salt thereof is provided. In the formula, the ring X represents: R 1 and R 2 independently represent a hydrogen atom, an alkyl group, an aryl group, an aromatic heterocyclic group or the like; R 3 represents a hydrogen atom, a halogen atom, a hydroxy group, an alkoxy group, an aryloxy group, an alkyl group, an aryl group, an amino group, an alkylamino group or the like; A 1 represents a sulfur atom or the like; and A 2 represents an alkylene group.

  本发明旨在研究具有嘧啶基烷基硫基团的新型环状化合物的合成，并找到这些化合物的药理作用。根据本发明，提供了由式（1）表示的化合物或其盐。其中，环X表示：R1和R2独立地表示氢原子、烷基、芳基、芳香杂环基或类似物；R3表示氢原子、卤原子、羟基、烷氧基、芳氧基、烷基、芳基、氨基、烷基氨基或类似物；A1表示硫原子或类似物；A2表示烷基链。
• Novel cyclic compound having quinolylalkylthio group
  申请人：Kawashima Kenji

  公开号：US20080021064A1

  公开（公告）日：2008-01-24

  The present invention relates to a synthesis study of novel cyclic compounds having a quinolylalkylthio group represented by the formula (1), and pharmacological actions of the compounds. In the formula, the ring X represents: which may have halogen and/or alkyl; R 1 and R 2 independently represent hydrogen, alkyl, cycloalkyl, aryl or a (non) aromatic heterocycle; R 3 represents qinolyl; A represents sulfur, sulfinyl or sulfonyl; and B represents alkylene.

  本发明涉及一种合成具有式（1）所表示的喹诺基烷基硫基的新型环状化合物的研究，以及所述化合物的药理作用。在该式中，环X代表：可能具有卤素和/或烷基；R1和R2独立地表示氢、烷基、环烷基、芳基或（非）芳香杂环；R3表示喹诺基；A表示硫、亚砜或磺酰基；B表示烷基。
• Novel cyclic compound having pyrimidinylalkylthio group
  申请人：Tajima Hisashi

  公开号：US20110124646A1

  公开（公告）日：2011-05-26

  A method of treating a disease associated with angiogenesis by administering a therapeutically effective amount of a compound represented by the formula (1) or a salt thereof wherein the ring X represents R 1 and R 2 independently represent a hydrogen atom, an alkyl, an aryl or an aromatic heterocyclic; R 3 represents a hydrogen atom, a halogen atom, a hydroxy, an alkoxy, an aryloxy, an alkyl, an aryl, an amino, an alkylamino, a cycloalkylamino, an arylamino, an alkylcarbonylamino, an arylcarbonylamino, a mercapto, an alkylthio, an arylthio, an alkylsulfinyl or a nonaromatic heterocyclic; A 1 represents a sulfur atom, a sulfinyl or a sulfonyl; and A 2 represents an alkylene.

  通过给予化合物公式（1）或其盐的治疗有效量，治疗与血管生成相关的疾病的方法，其中环X代表R1和R2分别代表氢原子，烷基，芳基或芳香族杂环；R3代表氢原子，卤原子，羟基，烷氧基，芳氧基，烷基，芳基，氨基，烷基氨基，环烷基氨基，芳基氨基，烷基羰基氨基，芳基羰基氨基，巯基，烷硫基，芳硫基，烷基亚磺酰基或非芳香族杂环；A1代表硫原子，亚磺酰基或磺酰基；A2代表烷基。
• Exploring the Versatility of the Amidation of Aryl Acid Fluorides using the Germylamines R₃GeNMe₂
  作者：Vanessa A. Fortney、Julia K. Murphy、Thad R. Stancil、Milan Gembicky、Arnold L. Rheingold、Charles S. Weinert

  DOI：10.1002/asia.202300788

  日期：2023.12.14

  The formation of amide bonds is an important process since this linkage is an essential component in proteins, pharmaceuticals, and other medicinally and biologically significant molecules. Recently, it was demonstrated that germylamines R₃GeNR’₂ were useful reagents for the conversion of acid fluorides to amides. This transformation occurs readily at room temperature and has a low activation energy. In the present study, the versatility of this amidation reaction with aryl acid fluorides is investigated. A series of thirteen acid fluorides with various substituents on the aromatic ring were reacted with the germylamine Ph₃GeNMe₂ and twelve of these were converted to the corresponding amides in high yields, the exception being 1,4‐benzenedicarbonyl difluoride. The germylamines Buⁿ₃GeNMe₂ and Prⁱ₃GeNMe₂ also could be used for this interconversion, and both of these species successfully converted 1,4‐benzenedicarbonyl difluoride to the corresponding amide. In addition, the crystal structure of Ph₃GeNMe₂ is reported. This represents one of only three crystallographically characterized germylamines. The synthesis and ¹⁹F NMR characterization of three fluorogermanes R₃GeF (R=Buⁿ, Prⁱ, and Mes) are also reported herein.

  摘要酰胺键的形成是一个重要的过程，因为这种连接是蛋白质、药物和其他具有药物和生物意义的分子的重要组成部分。最近的研究表明，胚芽胺 R3GeNR'2 是将酸性氟化物转化为酰胺的有用试剂。这种转化在室温下很容易发生，而且活化能很低。本研究探讨了这种与芳基酸性氟化物的酰胺化反应的多功能性。一系列在芳香环上具有不同取代基的 13 种酸氟化物与胚芽胺 Ph3GeNMe2 发生了反应，其中 12 种以高产率转化为相应的酰胺，1,4-苯二羰基二氟化物除外。胚芽胺 Bun3GeNMe2 和 Pri3GeNMe2 也可用于这种相互转化，它们都成功地将 1,4-苯二羰基二氟化物转化为相应的酰胺。此外，还报告了 Ph3GeNMe2 的晶体结构。这是仅有的三种具有晶体学特征的胚芽胺之一。本文还报道了三种氟锗（R3GeF，R=Bun、Pri 和 Mes）的合成和 19F NMR 表征。