tert-butyl 5-acetyloxycyclopent-1-enecarboxylate | 253443-19-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl 5-acetyloxycyclopent-1-enecarboxylate
• 英文别名: Tert-butyl 5-acetyloxycyclopentene-1-carboxylate
• CAS: 253443-19-5
• 化学式: C₁₂H₁₈O₄
• 分子量: 226.273
• InChiKey: RZIDOWDZPRLCHK-UHFFFAOYSA-N

物化性质

• 沸点：
  280.3±40.0 °C(predicted)
• 密度：
  1.08±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl 5-acetyloxycyclopent-1-enecarboxylate 在 哌啶 、 lithium aluminium tetrahydride 、 四(三苯基膦)钯 、 正丁基锂 、 3-乙基-3-戊醇 、 sodium carbonate 、 mercury dichloride 、 mercury(II) oxide 作用下， 以 四氢呋喃 、 乙醇 、 水 、 丙酮 、 甲苯 为溶剂， 反应 73.5h， 生成 (1S,2R,5S)-2-(Biphenyl-4-ylsulfanyl)-5-hydroxymethyl-cyclopentanecarboxylic acid tert-butyl ester
  参考文献：
  名称：

  Stereospecific Synthesis of 5-Substituted 2-Bisarylthiocyclopentane Carboxylic Acids as Specific Matrix Metalloproteinase Inhibitors

  摘要：

  The synthesis and structure-activity relationship (SAR) studies of a series of cyclopentane carboxylic acid matrix metalloproteinase (MMP) inhibitors are described. Potent and specific MMP-2, -3, -9, -13 inhibitors were obtained by regio- and stereoselective substitutions at positions 2 and 5 on the cyclopentane ring. Compounds 2a and 2e are active in the mouse B16-F10 metastasis model and display very good pharmacokinetic parameters.

  DOI：

  10.1021/jm0307638
• 作为产物：
  描述：

  二乙基膦酰基乙酸叔丁酯 在 吡啶 、 盐酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 tert-butyl 5-acetyloxycyclopent-1-enecarboxylate
  参考文献：
  名称：

  Stereospecific Synthesis of 5-Substituted 2-Bisarylthiocyclopentane Carboxylic Acids as Specific Matrix Metalloproteinase Inhibitors

  摘要：

  The synthesis and structure-activity relationship (SAR) studies of a series of cyclopentane carboxylic acid matrix metalloproteinase (MMP) inhibitors are described. Potent and specific MMP-2, -3, -9, -13 inhibitors were obtained by regio- and stereoselective substitutions at positions 2 and 5 on the cyclopentane ring. Compounds 2a and 2e are active in the mouse B16-F10 metastasis model and display very good pharmacokinetic parameters.

  DOI：

  10.1021/jm0307638

文献信息

• Stereospecific Synthesis of 5-Substituted 2-Bisarylthiocyclopentane Carboxylic Acids as Specific Matrix Metalloproteinase Inhibitors
  作者：Thierry Le Diguarher、Anne-Marie Chollet、Marc Bertrand、Philippe Hennig、Eric Raimbaud、Massimo Sabatini、Nicolas Guilbaud、Alain Pierré、Gordon C. Tucker、Patrick Casara

  DOI：10.1021/jm0307638

  日期：2003.8.1

  The synthesis and structure-activity relationship (SAR) studies of a series of cyclopentane carboxylic acid matrix metalloproteinase (MMP) inhibitors are described. Potent and specific MMP-2, -3, -9, -13 inhibitors were obtained by regio- and stereoselective substitutions at positions 2 and 5 on the cyclopentane ring. Compounds 2a and 2e are active in the mouse B16-F10 metastasis model and display very good pharmacokinetic parameters.