(E)-styryl 2-hydroxyphenyl sulfide | 847258-33-7

• 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: (E)-styryl 2-hydroxyphenyl sulfide
• 英文别名: (E)-2-(styrylthio)phenol；2-[(E)-2-phenylethenyl]sulfanylphenol
• CAS: 847258-33-7
• 化学式: C₁₄H₁₂OS
• 分子量: 228.315
• InChiKey: ROWVKPWGDMTCTF-ZHACJKMWSA-N

物化性质

• 熔点：
  92-94 °C
• 沸点：
  372.7±42.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-styryl 2-hydroxyphenyl sulfide 在 吡啶 、 双氧水 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 生成
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of (E)- and (Z)-styryl-2-acetoxyphenyl sulfides and sulfones as cyclooxygenase-2 inhibitors

  摘要：

  A new series of styryl acetoxyphenyl sulfides and sulfones possessing (E)- and (Z)-configurations were designed and prepared by stereospecific syntheses. All these compounds were evaluated for their ability to inhibit COX-2 enzyme in vitro. Structure-activity relationship studies on these compounds revealed that only sulfides with (Z)-configuration have potential COX-2 inhibitory activity. This inactivation of the enzyme is believed to be due to the selective covalent modification of COX-2 by the inhibitors. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.12.005
• 作为产物：
  描述：

  2-羟基苯硫酚 、 苯乙炔 在 manganese triacetate 、 溶剂黄146 作用下， 反应 0.03h， 以88%的产率得到(E)-styryl 2-hydroxyphenyl sulfide
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of (E)- and (Z)-styryl-2-acetoxyphenyl sulfides and sulfones as cyclooxygenase-2 inhibitors

  摘要：

  A new series of styryl acetoxyphenyl sulfides and sulfones possessing (E)- and (Z)-configurations were designed and prepared by stereospecific syntheses. All these compounds were evaluated for their ability to inhibit COX-2 enzyme in vitro. Structure-activity relationship studies on these compounds revealed that only sulfides with (Z)-configuration have potential COX-2 inhibitory activity. This inactivation of the enzyme is believed to be due to the selective covalent modification of COX-2 by the inhibitors. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.12.005

文献信息

• Synthesis of Vinyl Sulfides by Copper-Catalyzed Decarboxylative C−S Cross-Coupling
  作者：Sadananda Ranjit、Zhongyu Duan、Pengfei Zhang、Xiaogang Liu

  DOI：10.1021/ol101729k

  日期：2010.9.17

  A novel method for the synthesis of vinyl sulfides by the decarboxylative cross-coupling of arylpropiolic acids with thiols using copper(I) salts as catalysts has been developed. In the presence of Cul and Cs2CO3, a variety of thiols reacted with arylpropiolic acids to afford the corresponding vinyl sulfides in good to excellent yields with high stereoselectivity for Z-isomers.
• Design, synthesis, and biological evaluation of (E)- and (Z)-styryl-2-acetoxyphenyl sulfides and sulfones as cyclooxygenase-2 inhibitors
  作者：M.V. Ramana Reddy、Muralidhar Reddy Mallireddigari、Venkat R. Pallela、Padmavathi Venkatapuram、Rengasamy Boominathan、Stanley C. Bell、E. Premkumar Reddy

  DOI：10.1016/j.bmc.2004.12.005

  日期：2005.3.1

  A new series of styryl acetoxyphenyl sulfides and sulfones possessing (E)- and (Z)-configurations were designed and prepared by stereospecific syntheses. All these compounds were evaluated for their ability to inhibit COX-2 enzyme in vitro. Structure-activity relationship studies on these compounds revealed that only sulfides with (Z)-configuration have potential COX-2 inhibitory activity. This inactivation of the enzyme is believed to be due to the selective covalent modification of COX-2 by the inhibitors. (C) 2004 Elsevier Ltd. All rights reserved.