2-(4-Hydroxy-benzyl)-1,1-dioxo-tetrahydro-1λ6-thiophene-3-carboxylic acid methyl ester | 409108-04-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(4-Hydroxy-benzyl)-1,1-dioxo-tetrahydro-1λ6-thiophene-3-carboxylic acid methyl ester
• CAS: 409108-04-9
• 化学式: C₁₃H₁₆O₅S
• 分子量: 284.333
• InChiKey: VADIXMULAXVJJI-UHFFFAOYSA-N

物化性质

• 沸点：
  505.5±40.0 °C(Predicted)
• 密度：
  1.356±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.91
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  80.67
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-(4-Hydroxy-benzyl)-1,1-dioxo-tetrahydro-1λ6-thiophene-3-carboxylic acid methyl ester 在 盐酸羟胺 、 sodium methylate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 N-hydroxy-2-{4-[(2-methyl-4-quinolinyl)methoxy]benzyl}tetrahydro-3-thiophenecarboxamide 1,1-dioxide
  参考文献：
  名称：

  Conversion of potent MMP inhibitors into selective TACE inhibitors

  摘要：

  Novel sultam hydroxamates with potent MMP activity were transformed into potent TACE inhibitors, lacking MMP activity. To accomplish this we relied on structural differences between the MMP and TACE Sl' pockets and the known advantageous tit of a 2-methyl-4-quinolinylmethoxyphenyl group into this region. From this approach, compound 7d was identified as a potent TACE inhibitor (IC50 = 3.7 nM) that lacked MMP-1, -2, -9, and -13 activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.078
• 作为产物：
  描述：

  4-苄氧基苯甲醛 在 palladium dihydroxide 正丁基锂 、 氢气 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 二氯甲烷 为溶剂， 生成 2-(4-Hydroxy-benzyl)-1,1-dioxo-tetrahydro-1λ6-thiophene-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Conversion of potent MMP inhibitors into selective TACE inhibitors

  摘要：

  Novel sultam hydroxamates with potent MMP activity were transformed into potent TACE inhibitors, lacking MMP activity. To accomplish this we relied on structural differences between the MMP and TACE Sl' pockets and the known advantageous tit of a 2-methyl-4-quinolinylmethoxyphenyl group into this region. From this approach, compound 7d was identified as a potent TACE inhibitor (IC50 = 3.7 nM) that lacked MMP-1, -2, -9, and -13 activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.078