[4-(3-Morpholin-4-yl-3-oxoprop-1-enyl)-2,3-bis(trifluoromethyl)phenyl] trifluoromethanesulfonate | 869097-28-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: [4-(3-Morpholin-4-yl-3-oxoprop-1-enyl)-2,3-bis(trifluoromethyl)phenyl] trifluoromethanesulfonate
• 英文别名: [4-(3-morpholin-4-yl-3-oxoprop-1-enyl)-2,3-bis(trifluoromethyl)phenyl] trifluoromethanesulfonate
• CAS: 869097-28-9
• 化学式: C₁₆H₁₂F₉NO₅S
• 分子量: 501.327
• InChiKey: MPRNQZKHHACXFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  81.3
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  2-羟基苯硫酚 、 [4-(3-Morpholin-4-yl-3-oxoprop-1-enyl)-2,3-bis(trifluoromethyl)phenyl] trifluoromethanesulfonate 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 1.0h， 生成 3-[4-(2-Hydroxyphenyl)sulfanyl-2,3-bis(trifluoromethyl)phenyl]-1-morpholin-4-ylprop-2-en-1-one
  参考文献：
  名称：

  Structure–activity relationship of ortho- and meta-phenol based LFA-1 ICAM inhibitors

  摘要：

  LFA-1 ICAM inhibitors based on ortho- and meta-phenol templates were designed and synthesized by Mitsunobu chemistry. The selection of targets was guided by X-ray co-crystal data, and led to compounds which showed an up to 30-fold increase in potency over reference compound 1 in the LFA-1/ICAM1-Ig assay. The most active compound exploited a new hydrogen bond to the I-domain and exhibited subnanomolar potency. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.08.062
• 作为产物：
  描述：

  三氟甲磺酸酐 、 3-[4-Hydroxy-2,3-bis(trifluoromethyl)phenyl]-1-morpholin-4-ylprop-2-en-1-one 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 [4-(3-Morpholin-4-yl-3-oxoprop-1-enyl)-2,3-bis(trifluoromethyl)phenyl] trifluoromethanesulfonate
  参考文献：
  名称：

  Structure–activity relationship of ortho- and meta-phenol based LFA-1 ICAM inhibitors

  摘要：

  LFA-1 ICAM inhibitors based on ortho- and meta-phenol templates were designed and synthesized by Mitsunobu chemistry. The selection of targets was guided by X-ray co-crystal data, and led to compounds which showed an up to 30-fold increase in potency over reference compound 1 in the LFA-1/ICAM1-Ig assay. The most active compound exploited a new hydrogen bond to the I-domain and exhibited subnanomolar potency. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.08.062