(2S)-2-(6-methoxynaphthalen-2-yl)-2-methyloxirane | 159850-43-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2S)-2-(6-methoxynaphthalen-2-yl)-2-methyloxirane
• CAS: 159850-43-8
• 化学式: C₁₄H₁₄O₂
• 分子量: 214.264
• InChiKey: UPEGIZOAIZVQDQ-CQSZACIVSA-N

物化性质

• 沸点：
  353.1±22.0 °C(Predicted)
• 密度：
  1.158±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S)-2-(6-methoxynaphthalen-2-yl)-2-methyloxirane 在 palladium on activated charcoal chromium(VI) oxide 、 硫酸 、 hydroxide 、 氢气 作用下， 以 乙醇 为溶剂， 生成 萘普生
  参考文献：
  名称：

  Asymmetric dihydroxylation in an approach to the enantioselective synthesis of 2-arylpropanoic acid non-steroidal anti-inflammatory drugs

  摘要：

  Naproxen ((S)-2-(6-methoxy-2-naphthyl)propanoic acid) and flurbiprofen ((S)-2-(3-fluoro-4-phenylphenyl)propanoic acid) have been synthesised in high enantiomeric excess. The synthetic strategy employed was to introduce asymmetry into the molecules by Sharpless asymmetric dihydroxylation of the appropriate methyl styrenes. The resultant diols were then converted into optically active epoxides and the required stereogenic centre was assembled by catalytic hydrogenolysis of the introduced benzylic epoxide oxygen bond, followed by oxidation of the derived optically active primary alcohol. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00026-8
• 作为产物：
  描述：

  在 sodium hydride 作用下， 生成 (2S)-2-(6-methoxynaphthalen-2-yl)-2-methyloxirane
  参考文献：
  名称：

  Asymmetric dihydroxylation in an approach to the enantioselective synthesis of 2-arylpropanoic acid non-steroidal anti-inflammatory drugs

  摘要：

  Naproxen ((S)-2-(6-methoxy-2-naphthyl)propanoic acid) and flurbiprofen ((S)-2-(3-fluoro-4-phenylphenyl)propanoic acid) have been synthesised in high enantiomeric excess. The synthetic strategy employed was to introduce asymmetry into the molecules by Sharpless asymmetric dihydroxylation of the appropriate methyl styrenes. The resultant diols were then converted into optically active epoxides and the required stereogenic centre was assembled by catalytic hydrogenolysis of the introduced benzylic epoxide oxygen bond, followed by oxidation of the derived optically active primary alcohol. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00026-8

文献信息

• Engineering of Styrene Oxide Isomerase for Enhanced Production of 2-Arylpropionaldehydes: Chemoenzymatic Synthesis of (<i>S</i>)-Profens
  作者：Joel P. S. Choo、Fernanda L. Sirota、Willy W. L. See、Birgit Eisenhaber、Zhi Li

  DOI：10.1021/acscatal.3c02777

  日期：2023.9.1

  (S)-Arylpropionic acids are the pharmacologically active enantiomers of profen drugs that are challenging to synthesize chemically. Here, we report a chemoenzymatic synthesis of (S)-profens from alkenes involving styrene oxide isomerase (SOI)-catalyzed enantioretentive Meinwald-type isomerization of epoxides to aldehydes. This success relies on the engineering of SOI to accept larger substrates with

  ( S )-芳基丙酸是洛芬药物的药理活性对映体，化学合成具有挑战性。在这里，我们报告了（S)-丙芬涉及苯乙烯氧化物异构酶 (SOI) 催化的环氧化物对映 Meinwald 型异构化为醛。这一成功依赖于 SOI 的工程设计，以接受具有增强活性的更大底物，以进行限速异构化步骤，使用多和谐分析来指导定向进化，这代表了膜相关酶的首次成功的基于理性的进化，而无需结构信息。与野生型 SOI 相比，工程化 SOI-F35A/A131Y 的催化效率提高了 10.5 倍，并成功地与乙醛脱氢酶级联结合，从化学衍生的 (S)-环氧化物中产生了 83-4 种 (S ) -洛芬。 89% 产率和 90–94% ee。这项工作代表了一种从烯烃合成 ( S )-洛芬的简单而清洁的路线，并且工程化的 SOI 可用于生产其他类型的手性分子。
• Asymmetric dihydroxylation in an approach to the enantioselective synthesis of 2-arylpropanoic acid non-steroidal anti-inflammatory drugs
  作者：Robert C. Griesbach、David P.G. Hamon、Rebecca J. Kennedy

  DOI：10.1016/s0957-4166(97)00026-8

  日期：1997.2

  Naproxen ((S)-2-(6-methoxy-2-naphthyl)propanoic acid) and flurbiprofen ((S)-2-(3-fluoro-4-phenylphenyl)propanoic acid) have been synthesised in high enantiomeric excess. The synthetic strategy employed was to introduce asymmetry into the molecules by Sharpless asymmetric dihydroxylation of the appropriate methyl styrenes. The resultant diols were then converted into optically active epoxides and the required stereogenic centre was assembled by catalytic hydrogenolysis of the introduced benzylic epoxide oxygen bond, followed by oxidation of the derived optically active primary alcohol. (C) 1997 Elsevier Science Ltd.