(S)-F-ibuprofen | 911136-13-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (S)-F-ibuprofen
• 英文别名: (2S)-3-fluoro-2-[4-(2-methylpropyl)phenyl]propanoic acid
• CAS: 911136-13-5
• 化学式: C₁₃H₁₇FO₂
• 分子量: 224.275
• InChiKey: RHYPLXHTNFTLQW-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-F-ibuprofen 、 三甲基硅烷化重氮甲烷 在 溶剂黄146 作用下， 以 甲醇 、 苯 为溶剂， 以94%的产率得到
  参考文献：
  名称：

  铱催化氟双（苯磺酰基）甲烷的区域和对映选择性烯丙基烷基化。

  摘要：

  [Ir（COD）Cl]（2）/亚磷酰胺实现了氟双（苯磺酰基）甲烷（FBSM）的高度区域和对映选择性烯丙基烷基化，提供了带有末端烯烃的对映体纯的氟双（苯磺酰基）甲基化化合物，可以将其转化只需两步即可制得单氟甲基化布洛芬，而不会损失光学纯度（95％ee）。

  DOI：

  10.1039/b914315g
• 作为产物：
  描述：

  1-[(2R)-1,1-bis(benzenesulfonyl)-1-fluorobut-3-en-2-yl]-4-(2-methylpropyl)benzene 在 甲醇 、 ruthenium trichloride 、 sodium periodate 、 magnesium 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 反应 48.0h， 生成 (S)-F-ibuprofen
  参考文献：
  名称：

  Methyl-monofluorination of ibuprofen selectively increases its inhibitory activity toward cyclooxygenase-1 leading to enhanced analgesic activity and reduced gastric damage in vivo

  摘要：

  Newly developed monofluoromethylation reaction provided access to various bioactive molecules with an interesting monofluoromethyl unit. An iridium-catalyzed asymmetric version was employed for large-scale methyl-monofluorination of widely used nonsteroidal anti-inflammatory drug ibuprofen (the active S isoform). The methyl-monofluorinated ibuprofen was found to selectively inhibit cyclooxygenase-1 over cyclooxygenase-2 and surprisingly, the compound, with almost equal pharmacokinetic profile, was shown to increase analgesic activity and diminish gastric damage in animal models comparing to the parent drug ibuprofen. Therefore, methyl-monofluorination could be a useful strategy for improving efficacy and safety profile of drugs from the 'profen' family. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.114

文献信息

• Fluorobis(phenylsulfonyl)methane: A Fluoromethide Equivalent and Palladium-Catalyzed Enantioselective Allylic Monofluoromethylation
  作者：Takeo Fukuzumi、Norio Shibata、Masayoshi Sugiura、Hiroyuki Yasui、Shuichi Nakamura、Takeshi Toru

  DOI：10.1002/anie.200600625

  日期：2006.7.24
• Methyl-monofluorination of ibuprofen selectively increases its inhibitory activity toward cyclooxygenase-1 leading to enhanced analgesic activity and reduced gastric damage in vivo
  作者：Hong Su、Yuli Xie、Wen-Bo Liu、Shu-Li You

  DOI：10.1016/j.bmcl.2011.04.114

  日期：2011.6

  Newly developed monofluoromethylation reaction provided access to various bioactive molecules with an interesting monofluoromethyl unit. An iridium-catalyzed asymmetric version was employed for large-scale methyl-monofluorination of widely used nonsteroidal anti-inflammatory drug ibuprofen (the active S isoform). The methyl-monofluorinated ibuprofen was found to selectively inhibit cyclooxygenase-1 over cyclooxygenase-2 and surprisingly, the compound, with almost equal pharmacokinetic profile, was shown to increase analgesic activity and diminish gastric damage in animal models comparing to the parent drug ibuprofen. Therefore, methyl-monofluorination could be a useful strategy for improving efficacy and safety profile of drugs from the 'profen' family. (C) 2011 Elsevier Ltd. All rights reserved.
• Iridium-catalyzed regio- and enantioselective allylic alkylation of fluorobis(phenylsulfonyl)methane
  作者：Wen-Bo Liu、Sheng-Cai Zheng、Hu He、Xiao-Ming Zhao、Li-Xin Dai、Shu-Li You

  DOI：10.1039/b914315g

  日期：——

  Highly regio- and enantioselective allylic alkylation of fluorobis(phenylsulfonyl)methane (FBSM) has been realized by [Ir(COD)Cl](2)/phosphoramidite, affording enantiopure fluorobis(phenylsulfonyl)methylated compounds bearing a terminal alkene, which could be converted to monofluoro-methylated ibuprofen in just two steps without loss of the optical purity (95% ee).

  [Ir（COD）Cl]（2）/亚磷酰胺实现了氟双（苯磺酰基）甲烷（FBSM）的高度区域和对映选择性烯丙基烷基化，提供了带有末端烯烃的对映体纯的氟双（苯磺酰基）甲基化化合物，可以将其转化只需两步即可制得单氟甲基化布洛芬，而不会损失光学纯度（95％ee）。