(S)-2-hydroxy-2-methyl-3,4-dihydronaphthalen-1(2H)-one | 104322-64-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (S)-2-hydroxy-2-methyl-3,4-dihydronaphthalen-1(2H)-one
• 英文别名: 2-hydroxy-2-methyl-3,4-dihydro-2H-naphthalen-1-one；(S)-(+)-2-hydroxy-2-methyl-1-tetralone；(S)-(-)-2-hydroxy-2-methyl-1-tetralone；(S)-2-Hydroxy-2-methyl-1-tetralone；(S)-2-hydroxy-2-methyltetralone；2-hydroxy-2-methyl-1-tetralone；(2S)-2-hydroxy-2-methyl-3,4-dihydronaphthalen-1-one
• CAS: 104322-64-7
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: HAMPENXKJTUEGY-NSHDSACASA-N

物化性质

• 沸点：
  314.9±31.0 °C(Predicted)
• 密度：
  1.189±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-甲基-3,4-二氢-2H-1-萘酮 在 C₄₆H₅₂N₄O₂⁽²⁺⁾*2Br^(1-) 、 氧气 、 sodium hydroxide 、 亚磷酸三乙酯 作用下， 以 水 、 苯 为溶剂， 反应 72.0h， 以98%的产率得到(S)-2-hydroxy-2-methyl-3,4-dihydronaphthalen-1(2H)-one
  参考文献：
  名称：

  Phase-Transfer-Catalyzed Enantioselective α-Hydroxylation of Acyclic and Cyclic Ketones with Oxygen

  摘要：

  An efficient and enantioselective alpha-hydroxylation of acyclic as well as cyclic ketones using molecular oxygen has been developed. This simple catalytic procedure uses a readily available phase transfer catalyst and produces a wide range of valuable tertiary a-hydroxy ketones in good to excellent enantiopurity.

  DOI：

  10.1021/acscatal.5b00583

文献信息

• Flexible Stereoselective Functionalizations of Ketones through Umpolung with Hypervalent Iodine Reagents
  作者：Pushpak Mizar、Thomas Wirth

  DOI：10.1002/anie.201400405

  日期：2014.6.2

  The functionalization of carbonyl compounds in the α‐position has gathered much attention as a synthetic route because of the wide biological importance of such products. Through polarity reversal, or “umpolung”, we show here that typical nucleophiles, such as oxygen, nitrogen, and even carbon nucleophiles, can be used for addition reactions after tethering them to enol ethers. Our findings allow novel

  由于此类产品具有广泛的生物学重要性，因此羰基化合物在α位上的功能化作为合成途径已引起广泛关注。通过极性反转或“极性”，我们在这里表明典型的亲核试剂，例如氧，氮，甚至碳亲核试剂，在将它们束缚到烯醇醚后，可以用于加成反应。我们的发现可以进行新颖的逆合成规划，并可以快速组装以前只能通过多步序列访问的结构。
• New methods and reagents in organic synthesis. 75. asymmetric synthesis of α-hydroxy ketones using chiral phase transfer catalysts
  作者：Moriyasu Masui、Akira Ando、Takayuki Shioiri

  DOI：10.1016/0040-4039(88)85224-9

  日期：——

  Optically active α-hydroxy ketones are obtained by oxidation of achiral ketones with molecular oxygen in two phase system using chiral phase transfer catalysts.

  光学活性α-羟基酮是通过使用手性相转移催化剂在两相体系中用分子氧将非手性酮氧化而获得的。
• Chemistry of oxaziridines. 14. Asymmetric oxidation of ketone enolates using enantiomerically pure (camphorylsulfonyl)oxaziridine
  作者：Franklin A. Davis、Aurelia C. Sheppard、Bang Chi Chen、M. Serajul Haque

  DOI：10.1021/ja00174a035

  日期：1990.8

  Le mecanisme met en jeu une substitution de type SN2 de l'anion enolate sur l'oxaziridine via un etat de transition «ouvert»

  Le mecanisme 通过 un etat de transition «ouvert» 遇到 en jeu une 取代 SN2 型 de l'anion enolate sur l'oxaziridine
• (Camphorylsulfonyl)imine dianion in the synthesis of new optically pure (camphorylsulfonyl)oxaziridine derivatives
  作者：Franklin A. Davis、Michael C. Weismiller、G.Sankar Lal、Bang Chi Chen、Robert M. Przeslawski

  DOI：10.1016/s0040-4039(00)99534-0

  日期：1989.1

  New, more efficient enantiomerically pure (camphorylsulfonyl)oxaziridines are prepared by mono alkylation of the dianion of (camphorsulfonyl)imine at the carbon atom adjacent to the sulfonyl group.

  通过使（樟脑磺酰基）亚胺的二价阴离子在邻近磺酰基的碳原子上单烷基化来制备新的，更有效的对映体纯的（樟脑磺酰基）恶唑烷。
• Synthesis and Reactions of <i>exo</i>-Camphorylsulfonyloxaziridine
  作者：Franklin A. Davis、Rajarathnam E. Reddy、Parimala V. N. Kasu、Padma S. Portonovo、Patrick J. Carroll

  DOI：10.1021/jo961991v

  日期：1997.5.1

  The first example of an exo-camphorylsulfonyloxaziridine 4a was prepared by m-CPBA oxidation of camphor imine 9. This surprising result is due to the conformation of the imine which apparently prevents attack of the peracid from the endo direction. Similar oxidations of all other camphorsulfonylimines result in the endo-oxaziridine exclusively. Asymmetric oxidation of sulfides to sulfoxides and the alpha-hydroxylation of enolates by 4 can be interpreted in terms of open transition states where nonbonded interactions are minimized. These results support earlier conclusions and predictions of the stereoselectivity and mechanisms of molecular recognition by the N-sulfonyloxaziridine class of oxidizing reagents.