Dimethyl 2-[(3,4-difluorophenyl)sulfanyl-(2,3,6-trifluorophenyl)methyl]propanedioate | 1420649-45-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: Dimethyl 2-[(3,4-difluorophenyl)sulfanyl-(2,3,6-trifluorophenyl)methyl]propanedioate
• 英文别名: dimethyl 2-[(3,4-difluorophenyl)sulfanyl-(2,3,6-trifluorophenyl)methyl]propanedioate
• CAS: 1420649-45-1
• 化学式: C₁₈H₁₃F₅O₄S
• 分子量: 420.357
• InChiKey: BUQOKGLRTKPKQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  77.9
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Dimethyl 2-[(3,4-difluorophenyl)sulfanyl-(2,3,6-trifluorophenyl)methyl]propanedioate 在 lithium aluminium tetrahydride 、 三氟甲磺酸三甲基硅酯 、 三氟化硼乙醚 、 potassium tert-butylate 、 戴斯-马丁氧化剂 、 臭氧 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 2-[(4S,4aS,10bS)-10b-(3,4-difluorophenyl)sulfonyl-7,10-difluoro-2,4,4a,5-tetrahydro-1H-pyrano[3,4-c]chromen-4-yl]ethanol
  参考文献：
  名称：

  Structure activity relationship studies of tricyclic bispyran sulfone γ-secretase inhibitors

  摘要：

  An investigation is detailed of the structure activity relationships (SAR) of two sulfone side chains of compound (-)-1a (SCH 900229), a potent, PS1-selective gamma-secretase inhibitor and clinical candidate for the treatment of Alzheimer's disease. Specifically, 4-CF3 and 4-Br substituted arylsulfone analogs, (-)-1b and (-)-1c, are equipotent to compound (-)-1a. On the right hand side chain, linker size and terminal substituents of the pendant sulfone group are also investigated. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.047
• 作为产物：
  描述：

  2-(2,3,6-trifluoro-benzylidene)-malonic acid dimethyl ester 、 3,4-二氟苯硫酚 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到Dimethyl 2-[(3,4-difluorophenyl)sulfanyl-(2,3,6-trifluorophenyl)methyl]propanedioate
  参考文献：
  名称：

  Structure activity relationship studies of tricyclic bispyran sulfone γ-secretase inhibitors

  摘要：

  An investigation is detailed of the structure activity relationships (SAR) of two sulfone side chains of compound (-)-1a (SCH 900229), a potent, PS1-selective gamma-secretase inhibitor and clinical candidate for the treatment of Alzheimer's disease. Specifically, 4-CF3 and 4-Br substituted arylsulfone analogs, (-)-1b and (-)-1c, are equipotent to compound (-)-1a. On the right hand side chain, linker size and terminal substituents of the pendant sulfone group are also investigated. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.047

文献信息

• Structure activity relationship studies of tricyclic bispyran sulfone γ-secretase inhibitors
  作者：Wen-Lian Wu、Theodros Asberom、Thomas Bara、Chad Bennett、Duane A. Burnett、John Clader、Martin Domalski、William J. Greenlee、Hubert Josien、Mark McBriar、Murali Rajagopalan、Monica Vicarel、Ruo Xu、Lynn A. Hyde、Robert A. Del Vecchio、Mary E. Cohen-Williams、Lixin Song、Julie Lee、Giuseppe Terracina、Qi Zhang、Amin Nomeir、Eric M. Parker、Lili Zhang

  DOI：10.1016/j.bmcl.2012.11.047

  日期：2013.2

  An investigation is detailed of the structure activity relationships (SAR) of two sulfone side chains of compound (-)-1a (SCH 900229), a potent, PS1-selective gamma-secretase inhibitor and clinical candidate for the treatment of Alzheimer's disease. Specifically, 4-CF3 and 4-Br substituted arylsulfone analogs, (-)-1b and (-)-1c, are equipotent to compound (-)-1a. On the right hand side chain, linker size and terminal substituents of the pendant sulfone group are also investigated. (c) 2012 Elsevier Ltd. All rights reserved.