(S)-2-(6-methoxy-2-naphthyl)-1,2-propanediol | 159990-32-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-2-(6-methoxy-2-naphthyl)-1,2-propanediol
• 英文别名: (2S)-2-(6-methoxynaphthalen-2-yl)propane-1,2-diol
• CAS: 159990-32-6
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: IUJHXNDDQJJFPX-CQSZACIVSA-N

物化性质

• 沸点：
  440.8±30.0 °C(Predicted)
• 密度：
  1.205±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-(6-methoxy-2-naphthyl)-1,2-propanediol 在 palladium dihydroxide 氢气 、 chromium(VI) oxide 、 硫酸 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 2.0h， 以37%的产率得到萘普生
  参考文献：
  名称：

  A modification of the asymmetric dihydroxylation approach to the synthesis of (S)-2-arylpropanoic acids

  摘要：

  Catalytic hydrogenolysis of (S)-2-phenyl-1,2-propanediol (2), prepared by an asymmetric dihydroxylation of alpha-methylstyrene (1) with AD-mix-alpha, over Pearlman's catalyst gave (S)-2-phenyl-1-propanol (3). This method was applied to the synthesis of optically active 2-arylpropanoic acid antiinflammatory agents, (S)-ibuprofen (8) and (S)-naproxen (13). (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00279-3
• 作为产物：
  描述：

  6-甲氧基-2-乙酰萘 在 吡啶 、 四氧化锇 、 甲基磺酰胺 、 potassium carbonate 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 potassium hexacyanoferrate(III) 、 三氯氧磷 作用下， 以 乙醚 、 二氯甲烷 、 水 、 甲苯 、 叔丁醇 为溶剂， 反应 38.5h， 生成 (S)-2-(6-methoxy-2-naphthyl)-1,2-propanediol
  参考文献：
  名称：

  Nandanan; Jayachandran; Phukan, Prodeep, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1998, vol. 37, # 12, p. 1221 - 1227

  摘要：

  DOI：

文献信息

• New ligands double the scope of the catalytic asymmetric dihydroxylation of olefins
  作者：K. Barry Sharpless、Willi Amberg、Matthias Beller、Hou Chen、Jens Hartung、Yasuhiro Kawanami、Doris Lubben、Eric Manoury、Yasukazu Ogino、Tomoyuki Shibata、Tatsuzo Ukita

  DOI：10.1021/jo00015a001

  日期：1991.7.1

  Improved ligands render terminal olefins good substrates for the osmium-catalyzed asymmetric dihydroxylation (ADH) process, and the amounts of chiral ligand and osmium catalyst required diminish dramatically.
• 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.
• Nandanan; Jayachandran; Phukan, Prodeep, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1998, vol. 37, # 12, p. 1221 - 1227
  作者：Nandanan、Jayachandran、Phukan, Prodeep、Pais, Godwin C. G.、Sudalai

  DOI：——

  日期：——
• A modification of the asymmetric dihydroxylation approach to the synthesis of (S)-2-arylpropanoic acids
  作者：Hiroyuki Ishibashi、Momoe Maeki、Junko Yagi、Masashi Ohba、Tae Kanai

  DOI：10.1016/s0040-4020(99)00279-3

  日期：1999.5

  Catalytic hydrogenolysis of (S)-2-phenyl-1,2-propanediol (2), prepared by an asymmetric dihydroxylation of alpha-methylstyrene (1) with AD-mix-alpha, over Pearlman's catalyst gave (S)-2-phenyl-1-propanol (3). This method was applied to the synthesis of optically active 2-arylpropanoic acid antiinflammatory agents, (S)-ibuprofen (8) and (S)-naproxen (13). (C) 1999 Elsevier Science Ltd. All rights reserved.