(4R,1'S)-4-<1'-(4''-bromophenyl)ethyl>-2,2-dimethyl-1,3-dioxolane | 151774-96-8

• 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: (4R,1'S)-4-<1'-(4''-bromophenyl)ethyl>-2,2-dimethyl-1,3-dioxolane
• 英文别名: (4R)-4-[(1S)-1-(4-bromophenyl)ethyl]-2,2-dimethyl-1,3-dioxolane
• CAS: 151774-96-8
• 化学式: C₁₃H₁₇BrO₂
• 分子量: 285.181
• InChiKey: DFDPLBFPMIAMAM-CABZTGNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4R,1'S)-4-<1'-(4''-bromophenyl)ethyl>-2,2-dimethyl-1,3-dioxolane 在 palladium on activated charcoal 盐酸 、 水 、 氢气 、 叔丁基锂 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (2R,3S)-3-<4'-(2''-methylpropyl)phenyl>butane-1,2-diol
  参考文献：
  名称：

  对映选择性合成2-芳基丙酸非甾体抗炎药及相关化合物。

  摘要：

  （S）-2- [4'-（2″-甲基丙基）苯基丙酸（布洛芬）和（S）-2-（3'-苯甲酰基苯基）丙酸（酮洛芬）已经以高对映体过量的方式合成。立体化学的控制是通过Sharpless环氧化作用结合，然后对引入的苄基环氧化物氧键进行催化氢解来实现的。另外，通过以上方法制备的在钯存在下的有机化合物与对映纯的2-（3-碘苯基）丙酸和2-（4-碘苯基）丙酸的偶联是合成光学活性芳基丙酸的一般方法。酸。

  DOI：

  10.1016/0040-4020(95)00805-i
• 作为产物：
  描述：

  (2S,3S)-3-methyl-3-<4'-(trimethylsilyl)phenyl>oxiranemethanol 在 palladium on activated charcoal sodium hydroxide 、 N-氯代丁二酰亚胺 、 氢气 、 对甲苯磺酸 、 lithium bromide 作用下， 以 甲醇 为溶剂， 反应 12.75h， 生成 (4R,1'S)-4-<1'-(4''-bromophenyl)ethyl>-2,2-dimethyl-1,3-dioxolane
  参考文献：
  名称：

  对映选择性合成2-芳基丙酸非甾体抗炎药及相关化合物。

  摘要：

  （S）-2- [4'-（2″-甲基丙基）苯基丙酸（布洛芬）和（S）-2-（3'-苯甲酰基苯基）丙酸（酮洛芬）已经以高对映体过量的方式合成。立体化学的控制是通过Sharpless环氧化作用结合，然后对引入的苄基环氧化物氧键进行催化氢解来实现的。另外，通过以上方法制备的在钯存在下的有机化合物与对映纯的2-（3-碘苯基）丙酸和2-（4-碘苯基）丙酸的偶联是合成光学活性芳基丙酸的一般方法。酸。

  DOI：

  10.1016/0040-4020(95)00805-i

文献信息

• Enantioselective synthesis of the four isomers of the biologically active metabolite of the 2-arylpropanoic acid NSAID, ximoprofen, and assessment of their inhibitory activity on human platelet cyclo-oxygenase in vitro
  作者：David P.G. Hamon、Peter J. Hayball、Ralph A. Massy-Westropp、Josephine L. Newton、Julie G. Tamblyn

  DOI：10.1016/0957-4166(95)00443-2

  日期：1996.1

  The four stereoisomers of the parent keto acid of the oximino drug ximoprofen have been prepared in high enantiomeric purity. The stereochemistry in the propionic acid chain was established by the combination of Sharpless epoxidation followed by stereoselective hydrogenolysis of the benzylic carbon-oxygen bond with inversion of configuration. The stereochemistry of the centre in the cyclohexanone ring was controlled by the stereoselective conjugate addition of the arylpropanoic acid moiety to the enantiomers of 5-(trimethylsilyl)-2-cyclohexenone with subsequent removal of the trimethylsilyl group. The pharmacological activity of each of the four isomers of the keto acid parent of ximoprofen were assessed by their in vitro inhibition of human platelet cyclo-oxygenase. As expected, the (S) configuration of the propionic acid chain was essential for activity but it was also found that the stereochemistry in the cyclohexanone moiety was important. Attempts to separate the (E) and (Z) isomers of the oxime derivative from one of the stereoisomers were unsuccessful.
• Concerning the enantioselective synthesis of the isomers of the arylpropanoic acid NSAID ximoprofen
  作者：David P.G. Hamon、Ralph A. Massy-Westropp、Josephine L. Newton

  DOI：10.1016/s0040-4039(00)79970-9

  日期：1994.2

  All four stereoisomers of the parent ketone of the oximido drug ximoprofen have been prepared pure. An attempt to isolate the pure E and Z isomers of the oxime derivative from one of these stereoisomers was unsuccessful.
• Asymmetric synthesis of ibuprofen and ketoprofen
  作者：David P.G. Hamon、Ralph A. Massy-Westropp、Josephine L. Newton

  DOI：10.1016/s0957-4166(00)80334-1

  日期：1993.7

  (S)-2-[4'-(2''-Methylpropyl)phenyl]propanoic acid (ibuprofen) and (S)-2-(3'-benzoylphenyl)propanoic acid (ketoprofen) have been synthesis in high enantiomeric excess. Control of the stereochemistry was achieved by a combination of Sharpless epoxidation followed by catalytic hydrogenolysis of the introduced benzylic epoxide oxygen bond.
• Enantioselective syntheses of 2-arylpropanoic acid non-steroidal antiinflammatory drugs and related compounds.
  作者：David P.G. Hamon、Ralph A. Massy-Westropp、Josephine L. Newton

  DOI：10.1016/0040-4020(95)00805-i

  日期：1995.11

  Control of stereochemistry was achieved by a combination of Sharpless epoxidalion followed by catalytic hydrogenolysis of the introduced benzylic epoxide oxygen bond. Also, the coupling of organic compounds in the presence of palladium with enantiopure 2-(3-iodophenyl)propanoic and 2-(4-iodophenyl)propanoic acids, prepared by the methodology above, is a general method for the synthesis of optically active

  （S）-2- [4'-（2″-甲基丙基）苯基丙酸（布洛芬）和（S）-2-（3'-苯甲酰基苯基）丙酸（酮洛芬）已经以高对映体过量的方式合成。立体化学的控制是通过Sharpless环氧化作用结合，然后对引入的苄基环氧化物氧键进行催化氢解来实现的。另外，通过以上方法制备的在钯存在下的有机化合物与对映纯的2-（3-碘苯基）丙酸和2-（4-碘苯基）丙酸的偶联是合成光学活性芳基丙酸的一般方法。酸。