3-[(4-hydroxyphenyl)sulfanyl]cyclopentanone | 1069086-87-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-[(4-hydroxyphenyl)sulfanyl]cyclopentanone
• 英文别名: 3-(4-Hydroxyphenyl)sulfanylcyclopentan-1-one；3-(4-hydroxyphenyl)sulfanylcyclopentan-1-one
• CAS: 1069086-87-8
• 化学式: C₁₁H₁₂O₂S
• 分子量: 208.281
• InChiKey: ITNCZBWTIGOSIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[(4-hydroxyphenyl)sulfanyl]cyclopentanone 在 sodium tetrahydroborate 作用下， 生成 4-(3-hydroxycyclopentyl)sulfanylphenol
  参考文献：
  名称：

  Novel thiol-based TACE inhibitors. Part 2: Rational design, synthesis, and SAR of thiol-containing aryl sulfones

  摘要：

  A series of potent thiol-containing aryl sulfone TACE inhibitors were designed and synthesized. The SAR and MMP selectivity of the series were investigated. In particular, compound 8b showed excellent in vitro potency against the isolated enzyme and good selectivity over MMP-2, -7, -8, -9, and -13. The X-ray structure of 8b in complex with TACE was also obtained.

  DOI：

  10.1016/j.bmcl.2007.11.014
• 作为产物：
  描述：

  2-环戊烯酮 、 4,4’-二羟基二苯二硫醚 在 水 、 potassium carbonate 、 三苯基膦 作用下， 以 异丙醇 为溶剂， 反应 0.5h， 以82%的产率得到3-[(4-hydroxyphenyl)sulfanyl]cyclopentanone
  参考文献：
  名称：

  Development of a Tandem Base-Catalyzed, Triphenylphosphine-Mediated Disulfide Reduction-Michael Addition

  摘要：

  使用游离和聚合物结合的三苯基膦作为还原剂，开发了串联二硫还原-迈克尔加成法。该程序被应用于分子间体系，用于合成芳基硫酰基和烷基硫酰基取代的丙酸酯和相关酮类，以及分子内体系，用于合成苯并噻嗪酮衍生物。

  DOI：

  10.1055/s-2008-1067102

文献信息

• Novel thiol-based TACE inhibitors. Part 2: Rational design, synthesis, and SAR of thiol-containing aryl sulfones
  作者：Upul K. Bandarage、Tiansheng Wang、Jon H. Come、Emanuele Perola、Yunyi Wei、B. Govinda Rao

  DOI：10.1016/j.bmcl.2007.11.014

  日期：2008.1

  A series of potent thiol-containing aryl sulfone TACE inhibitors were designed and synthesized. The SAR and MMP selectivity of the series were investigated. In particular, compound 8b showed excellent in vitro potency against the isolated enzyme and good selectivity over MMP-2, -7, -8, -9, and -13. The X-ray structure of 8b in complex with TACE was also obtained.
• Development of a Tandem Base-Catalyzed, Triphenylphosphine-Mediated Disulfide Reduction-Michael Addition
  作者：Alessandra Bartolozzi、Hope Foudoulakis、Bridget Cole

  DOI：10.1055/s-2008-1067102

  日期：——

  A tandem disulfide reduction-Michael addition was developed using both free and polymer-bound triphenylphosphine as the reducing agent. The procedure was applied to intermolecular systems for the synthesis of arylsulfanyl- and alkylsulfanyl-substituted propanoates and related ketones, and to an intramolecular system for the synthesis of a benzothiazepinone derivative.

  使用游离和聚合物结合的三苯基膦作为还原剂，开发了串联二硫还原-迈克尔加成法。该程序被应用于分子间体系，用于合成芳基硫酰基和烷基硫酰基取代的丙酸酯和相关酮类，以及分子内体系，用于合成苯并噻嗪酮衍生物。