2-Cyano-N-[3-(methylthio)phenyl]acetamide | 591734-93-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-Cyano-N-[3-(methylthio)phenyl]acetamide
• 英文别名: 2-cyano-N-(3-methylsulfanylphenyl)acetamide
• CAS: 591734-93-9
• 化学式: C₁₀H₁₀N₂OS
• mdl: MFCD04084702
• 分子量: 206.268
• InChiKey: QFMKPKXRQUWOKB-UHFFFAOYSA-N

物化性质

• 沸点：
  447.3±30.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  78.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Cyano-N-[3-(methylthio)phenyl]acetamide 在 过氧乙酸 、 sodium hydride 作用下， 反应 3.0h， 生成 1-cyano-2-hydroxy-N-[3-(methylsulfonyl)phenyl]but-2-enamide
  参考文献：
  名称：

  Three leflunomide metabolite analogs

  摘要：

  The title compounds, 1-cyano-2-hydroxy-N-[4-(methylsulfonyl)phenyl]but-2-enamide, C12H12N2O4 S, PHI492, 1-cyano-2-hydroxy-N-[3-(methylsulfonyl)phenyl]but-2-enamide, C12H12N2O4S, PHI493, and N-[3-bromo-4-(trifluoromethoxy)phenyl]-1-cyano-2-hydroxybut-2-enamide, C12H8BrF3N2O3, PHI495, are potent inhibitors of Bruton's tyrosine kinase (BTK). The molecular structures of these compounds are similar and they display similar hydrogen-bonding networks and crystal packing. Examination of the crystal-packing interaction in the three compounds reveals an alternating direction of adjacent molecules in the crystalline lattice due to intermolecular cyano-amide hydrogen bonding. PHI492, a positional isomer of PHI493, does not form intermolecular O-H . . . O hydrogen bonds between molecules and crystallizes in a space group different from that of PHI493 and PHI495. The aromatic ring and the amide group of each molecule form a conjugated pi -system which ensures planarity, with further stabilization gained from intramolecular O-H . . . O hydrogen bonds.

  DOI：

  10.1107/s0108270100009768
• 作为产物：
  描述：

  3-氨基茴香硫醚 、 氰乙酸 在 N,N'-二异丙基碳二亚胺 作用下， 生成 2-Cyano-N-[3-(methylthio)phenyl]acetamide
  参考文献：
  名称：

  Three leflunomide metabolite analogs

  摘要：

  The title compounds, 1-cyano-2-hydroxy-N-[4-(methylsulfonyl)phenyl]but-2-enamide, C12H12N2O4 S, PHI492, 1-cyano-2-hydroxy-N-[3-(methylsulfonyl)phenyl]but-2-enamide, C12H12N2O4S, PHI493, and N-[3-bromo-4-(trifluoromethoxy)phenyl]-1-cyano-2-hydroxybut-2-enamide, C12H8BrF3N2O3, PHI495, are potent inhibitors of Bruton's tyrosine kinase (BTK). The molecular structures of these compounds are similar and they display similar hydrogen-bonding networks and crystal packing. Examination of the crystal-packing interaction in the three compounds reveals an alternating direction of adjacent molecules in the crystalline lattice due to intermolecular cyano-amide hydrogen bonding. PHI492, a positional isomer of PHI493, does not form intermolecular O-H . . . O hydrogen bonds between molecules and crystallizes in a space group different from that of PHI493 and PHI495. The aromatic ring and the amide group of each molecule form a conjugated pi -system which ensures planarity, with further stabilization gained from intramolecular O-H . . . O hydrogen bonds.

  DOI：

  10.1107/s0108270100009768

文献信息

• TETRACYCLIC INHIBITORS OF JANUS KINASES
  申请人：Rodgers James D.

  公开号：US20090215766A1

  公开（公告）日：2009-08-27

  The present invention provides compounds that modulate the activity of Janus kinases and are useful in the treatment of diseases related to activity of Janus kinases including, for example, immune-related diseases and cancer.

  本发明提供了一种可以调节Janus激酶活性的化合物，这些化合物可用于治疗与Janus激酶活性相关的疾病，例如免疫相关疾病和癌症。
• Three leflunomide metabolite analogs
  作者：Sutapa Ghosh、Jason D. Jennissen、Yaguo Zheng、Fatih M. Uckun

  DOI：10.1107/s0108270100009768

  日期：2000.10.15

  The title compounds, 1-cyano-2-hydroxy-N-[4-(methylsulfonyl)phenyl]but-2-enamide, C12H12N2O4 S, PHI492, 1-cyano-2-hydroxy-N-[3-(methylsulfonyl)phenyl]but-2-enamide, C12H12N2O4S, PHI493, and N-[3-bromo-4-(trifluoromethoxy)phenyl]-1-cyano-2-hydroxybut-2-enamide, C12H8BrF3N2O3, PHI495, are potent inhibitors of Bruton's tyrosine kinase (BTK). The molecular structures of these compounds are similar and they display similar hydrogen-bonding networks and crystal packing. Examination of the crystal-packing interaction in the three compounds reveals an alternating direction of adjacent molecules in the crystalline lattice due to intermolecular cyano-amide hydrogen bonding. PHI492, a positional isomer of PHI493, does not form intermolecular O-H . . . O hydrogen bonds between molecules and crystallizes in a space group different from that of PHI493 and PHI495. The aromatic ring and the amide group of each molecule form a conjugated pi -system which ensures planarity, with further stabilization gained from intramolecular O-H . . . O hydrogen bonds.