(S)-flurbiprofen ethyl ester

• 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: (S)-flurbiprofen ethyl ester
• 英文别名: ethyl (2S)-2-(3-fluoro-4-phenylphenyl)propanoate
• 化学式: C₁₇H₁₇FO₂
• 分子量: 272.319
• InChiKey: JIYXQCWLSQSIJV-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-flurbiprofen ethyl ester 在 碘 、 一水合肼 、 溶剂黄146 、 potassium hydroxide 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 生成 2-(1-(2-fluoro-[1,1′-biphenyl]-4-yl)ethyl)-5-(naphthalen-1-yl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Novel flurbiprofen clubbed oxadiazole derivatives as potential urease inhibitors and their molecular docking study

  摘要：

  合成氟比洛芬基噁二唑衍生物作为强效尿素酶抑制剂。

  DOI：

  10.1039/d3ra03841f
• 作为产物：
  描述：

  4-溴-2-氟联苯 在 氯化镍二甲氧基乙烷 、 magnesium 、 (R,R)-2,2'-异亚丙基双(4-苯基-2-恶唑啉) 作用下， 以 四氢呋喃 为溶剂， 反应 22.58h， 生成 (R)-flurbiprofen ethyl ester 、 (S)-flurbiprofen ethyl ester
  参考文献：
  名称：

  METHOD FOR PRODUCING OPTICALLY ACTIVE 2-(2-FLUOROBIPHENYL-4-YL) PROPANOIC ACID

  摘要：

  揭示了一种生产光学活性2-(2-氟联苯基-4-基)丙酸的新工艺。该生产工艺的特点在于，化合物[1]与镁等反应，制备有机金属试剂，然后在存在催化量的镍化合物和光学活性化合物[3]的存在下，与化合物[2]发生反应，得到化合物[4]，随后将其转化为化合物[5]或其药用可接受的盐。

  公开号：

  US20180282252A1

文献信息

• Biotransformation with whole microbial systems in a continuous flow reactor: resolution of (RS)-flurbiprofen using Aspergillus oryzae by direct esterification with ethanol in organic solvent
  作者：Lucia Tamborini、Diego Romano、Andrea Pinto、Martina Contente、Maria C. Iannuzzi、Paola Conti、Francesco Molinari

  DOI：10.1016/j.tetlet.2013.08.119

  日期：2013.11

  Cell-bound lipases of dry mycelium of Aspergillus oryzae were used in organic solvent for the resolution of racemic flurbiprofen by direct esterification with ethanol in a flow-chemistry reactor. Under flow conditions a significant reduction of the reaction time and an increase of the enantioselectivity were achieved compared to the batch mode. Moreover, the process was implemented by adding an in-line purification step integrated with the racemization of the unreacted flurbiprofen directly into a polymer-supported resin. (C) 2013 Elsevier Ltd. All rights reserved.
• Resolution of (R,S)-flurbiprofen catalysed by dry mycelia in organic solvent
  作者：Patrizia Spizzo、Alessandra Basso、Cynthia Ebert、Lucia Gardossi、Valerio Ferrario、Diego Romano、Francesco Molinari

  DOI：10.1016/j.tet.2007.08.051

  日期：2007.11

  Mycelia of Aspergillus oryzae display high enantioselectivity towards (R)-flurbiprofen and can be efficiently used in pure organic solvent for the resolution of (R,S)-flurbiprofen through esterification. The use of the lyophilized mycelia facilitates the separation process so that in one step the two enantiomers of flurbiprofen, which are both valuable for pharmaceutical applications, can be easily separated. The biotransformation can be carried out in different apolar solvents using different primary alcohols as nucleophiles under very mild conditions. (c) 2007 Elsevier Ltd. All rights reserved.
• METHOD FOR PRODUCING OPTICALLY ACTIVE 2-(2-FLUOROBIPHENYL-4-YL) PROPANOIC ACID
  申请人：TAISHO PHARMACEUTICAL CO., LTD.

  公开号：US20180282252A1

  公开（公告）日：2018-10-04

  A novel process for producing optically active 2-(2-fluorobiphenyl-4-yl)propanoic acid is disclosed. This production process is characterized in that a compound of formula [1] is reacted with magnesium and so forth to prepare an organometallic reagent, which is reacted with a compound of formula [2] in the presence of a catalytic amount of a nickel compound and a catalytic amount of an optically active compound of formula [3] to obtain a compound represented by formula [4] which is subsequently converted to a compound represented by formula [5] or a pharmaceutically acceptable salt thereof.

  揭示了一种生产光学活性2-(2-氟联苯基-4-基)丙酸的新工艺。该生产工艺的特点在于，化合物[1]与镁等反应，制备有机金属试剂，然后在存在催化量的镍化合物和光学活性化合物[3]的存在下，与化合物[2]发生反应，得到化合物[4]，随后将其转化为化合物[5]或其药用可接受的盐。
• Novel flurbiprofen clubbed oxadiazole derivatives as potential urease inhibitors and their molecular docking study
  作者：Sajjad Ahmad、Momin Khan、Aftab Alam、Amar Ajmal、Abdul Wadood、Azim Khan、Abdullah F. AlAsmari、Metab Alharbi、Abdulrahman Alshammari、Abdul Shakoor

  DOI：10.1039/d3ra03841f

  日期：——

  Synthesis of flurbiprofen based oxadiazole derivatives as potent urease inhibitors.

  合成氟比洛芬基噁二唑衍生物作为强效尿素酶抑制剂。