N-甲氧基-N,5-二甲基噻吩-2-甲酰胺 | 132960-12-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: N-甲氧基-N,5-二甲基噻吩-2-甲酰胺
• 英文名称: N-methoxy-N,5-dimethylthiophene-2-carboxamide
• 英文别名: 5-methyl-thiophene-2-carboxylic acid methoxy-methyl-amide
• CAS: 132960-12-4
• 化学式: C₈H₁₁NO₂S
• mdl: MFCD11616713
• 分子量: 185.247
• InChiKey: QXLYHESQCOQIEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.375
• 拓扑面积：
  57.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-甲氧基-N,5-二甲基噻吩-2-甲酰胺 在 palladium dihydroxide sodium tetrahydroborate 、 氢气 作用下， 以 甲醇 、 二氯甲烷 、 异丙醇 为溶剂， 20.0~50.0 ℃ 、344.75 kPa 条件下， 反应 50.0h， 生成 4(5)-(5-methylthiophen-2-ylmethyl)-1H-imidazole
  参考文献：
  名称：

  α₂ Adrenoceptor Agonists as Potential Analgesic Agents. 3. Imidazolylmethylthiophenes

  摘要：

  A series of imidazolylmethylthiophenes has been prepared and evaluated as ligands for the at adrenoceptor. These compounds were tested in two animal models that are predictive of analgesic activity in humans. The 3-thienyl compounds were generally the most potent, particularly those with substitution in the 4-position. A subset of the most active compounds was further evaluated for adverse cardiovascular effects in the anesthetized rat model. In addition to excellent binding at the alpha (2D) adrenoceptor, the 4-bromo analogues 20e and 21e were very active in the rat abdominal irritant test (RAIT) with ED50 doses of 0.38 and 0.31 mg/kg, respectively. We constructed a pharmacophore model based on the biological activity of the present series, dexmedetomidine (1), and conformationally restrained analogues 3 and 4.

  DOI：

  10.1021/jm0003891
• 作为产物：
  描述：

  5-甲基-2-噻吩甲酸 在 氯化亚砜 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 2.0h， 生成 N-甲氧基-N,5-二甲基噻吩-2-甲酰胺
  参考文献：
  名称：

  α₂ Adrenoceptor Agonists as Potential Analgesic Agents. 3. Imidazolylmethylthiophenes

  摘要：

  A series of imidazolylmethylthiophenes has been prepared and evaluated as ligands for the at adrenoceptor. These compounds were tested in two animal models that are predictive of analgesic activity in humans. The 3-thienyl compounds were generally the most potent, particularly those with substitution in the 4-position. A subset of the most active compounds was further evaluated for adverse cardiovascular effects in the anesthetized rat model. In addition to excellent binding at the alpha (2D) adrenoceptor, the 4-bromo analogues 20e and 21e were very active in the rat abdominal irritant test (RAIT) with ED50 doses of 0.38 and 0.31 mg/kg, respectively. We constructed a pharmacophore model based on the biological activity of the present series, dexmedetomidine (1), and conformationally restrained analogues 3 and 4.

  DOI：

  10.1021/jm0003891

文献信息

• ARYL FLUOROETHYL UREAS ACTING AS ALPHA 2 ADRENERGIC AGENTS
  申请人：Chow Ken

  公开号：US20080194650A1

  公开（公告）日：2008-08-14

  The invention provides well-defined aryl fluoroethyl ureas that are useful as selective alpha 2 adrenergic agonists. As such, the compounds described herein are useful in treating a wide variety of disorders associated with modulation of alpha 2 adrenergic receptors.

  本发明提供明确定义的芳基氟代乙基脲，用作选择性的α2肾上腺素能激动剂。因此，所述化合物可用于治疗与α2肾上腺素能受体调节相关的一系列疾病。
• Palladium-Catalyzed Preparation of Weinreb Amides from Boronic Acids and <i>N</i>-Methyl-<i>N</i>-methoxycarbamoyl Chloride
  作者：Ravi Krishnamoorthy、Sang Q. Lam、Christopher M. Manley、R. Jason Herr

  DOI：10.1021/jo902647h

  日期：2010.2.19

  A simple protocol for the synthesis of Weinreb benzamides and α,β-unsaturated Weinreb amides through a palladium-catalyzed cross-coupling reaction between organoboronic acids and N-methoxy-N-methylcarbamoyl chloride has been developed. The method is also applicable to the use of potassium organotrifluoroborates.

  已经开发了通过有机硼酸与N-甲氧基-N-甲基氨基甲酰氯之间的钯催化交叉偶联反应合成Weinreb苯甲酰胺和α，β-不饱和Weinreb酰胺的简单方案。该方法也适用于有机三氟硼酸钾的使用。
• Use of N,N'-dimethoxy-N,N'-dimethylurea as a carbonyl dication equivalent in organometallic addition reactions. Synthesis of unsymmetrical ketones
  作者：Wesley L. Whipple、Hans J. Reich

  DOI：10.1021/jo00008a057

  日期：1991.4
• WHIPPLE, WESLEY L.;REICH, HANS J., J. ORG. CHEM., 56,(1991) N, C. 476-480
  作者：WHIPPLE, WESLEY L.、REICH, HANS J.

  DOI：——

  日期：——
• US8557853B2
  申请人：——

  公开号：US8557853B2

  公开（公告）日：2013-10-15