(S)-(-)-2-Hydroxy-1-(6-methoxy-2-naphthyl)-1-propanone | 111197-81-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-(-)-2-Hydroxy-1-(6-methoxy-2-naphthyl)-1-propanone
• 英文别名: (2S)-2-hydroxy-1-(6-methoxynaphthalen-2-yl)propan-1-one
• CAS: 111197-81-0
• 化学式: C₁₄H₁₄O₃
• 分子量: 230.263
• InChiKey: WPVJMTCCWVSVIJ-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-(-)-2-Hydroxy-1-(6-methoxy-2-naphthyl)-1-propanone 在 三乙基铝 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (S)-3-(6-甲氧基-2-萘基)丁烷-2-酮
  参考文献：
  名称：

  频哪醇型反应不对称合成萘普生

  摘要：

  （S）-萘普生的合成中使用了不对称的频哪醇型重排。邻二醇的频哪醇型反应提供了α-芳基酮，其在甲醇存在下用次氯酸钠氧化成萘普生的甲酯。

  DOI：

  10.1016/s0957-4166(00)86058-9
• 作为产物：
  描述：

  2-甲氧基-1-(6-甲氧基萘-2-基)丙烷-1-酮 在 水 、 氢气 作用下， 生成 (S)-(-)-2-Hydroxy-1-(6-methoxy-2-naphthyl)-1-propanone
  参考文献：
  名称：

  Enzymes in organic synthesis: Lipase catalyzed resolution of secondary α-ketoalcohols

  摘要：

  Resolution of several alpha-ketoalcohols of synthetic value using lipase as a catalyst is described.

  DOI：

  10.1016/s0957-4166(00)80419-x

文献信息

• A General Synthetic Method of Chiral 2-Arylalkanoic Esters via Thermal 1,2-Rearrangement
  作者：Yutaka Honda、Aiichiro Ori、Gen-ichi Tsuchihashi

  DOI：10.1246/bcsj.60.1027

  日期：1987.3

  (S)-1-Aryl-2-sulfonyloxy-1-alkanone acetals, prepared from natural ethyl (S)-lactate or (S)-valine (chiral sources) by the use of a Grignard reaction, were rearranged under hydrolytic conditions in the presence of a base to give (S)-2-arylalkanoic esters which, in general, showed much higher pharmacological activities than their antipodes.

  (S)-1-芳基-2-磺酸酯-1-烷酮缩醛，由天然的乙基(S)-乳酸或(S)-缬氨酸（手性来源）通过格氏反应制备，在碱的存在下在水解条件下重新排列，生成了(S)-2-芳基烷酸酯，这些酯的药理活性通常明显高于其对映体。
• Optically active alpha-substituted aryl ketones, their preparation and their use in preparing alpha-arylalkanoic acids
  申请人：SYNTEX PHARMACEUTICALS INTERNATIONAL LIMITED

  公开号：EP0081993A2

  公开（公告）日：1983-06-22

  Pharmaceutically useful optically active a-arylalkanoic acids of the formula where Ar is aryl and R1 is alkyl or cycloalkyl or esters,ortho esters, or amides thereof are stereoselectively prepared by contacting a reagent of the formula Ar-MX, (Ar) 2M or ArM' where M is Cd, Cu(II), Mn(II), Mg or Zn, and M' is Cu(I) or Li, and X is halogen, with an optically active compound of the formula where Z is a leaving group and Y is halogen, acyloxy or where R' and R" are alkyl, aryl or with N are a heterocyclic group, to form the optically active ketone of the formula which is ketalized and rearranged to said acid, ester, ortho ester or amide. Alternatively, said ketone is reduced to the corresponding alkanol, which is rearranged to the a-arylalkanal. The alkanal so produced is converted to said acid by conventional methods.

  式中 Ar 为芳基，R1 为烷基或环烷基的具有光学活性的 a-芳基烷酸或其酯、正酯或酰胺，可通过与式中的试剂 其中 Ar 为芳基，R1 为烷基或环烷基或其酯、正交酯或酰胺，通过将式 Ar-MX、(Ar) 2M 或 ArM'（其中 M 为 Cd、Cu(II)、Mn(II)、Mg 或 Zn，M'为 Cu(I) 或 Li，X 为卤素）的试剂与式中的光学活性化合物接触，立体选择性地制备。 其中 Z 是离去基团，Y 是卤素、酰氧基或 其中 R'和 R "为烷基、芳基或与 N 一起为杂环基团，形成式中的光学活性酮。 经酮化后重新排列为所述的酸、酯、正交酯或酰胺。或者，将所述酮还原为相应的烷醇，再重新排列为 a-芳基烷醛。生成的烷醛通过常规方法转化为所述的酸。
• Duh, Tsai-Hui; Wang, Yi-Fong; Wu, Ming-Jung, Journal of the Chinese Chemical Society, 1995, vol. 42, # 3, p. 579 - 584
  作者：Duh, Tsai-Hui、Wang, Yi-Fong、Wu, Ming-Jung

  DOI：——

  日期：——
• Synthesis and Rhizopus oryzae mediated enantioselective hydrolysis of α-acetoxy aryl alkyl ketones
  作者：Ayhan S Demir、Haluk Hamamci、Cihangir Tanyeli、Idris M Akhmedov、Fatos Doganel

  DOI：10.1016/s0957-4166(98)00165-7

  日期：1998.5

  Mn(OAc)(3) oxidation of aromatic ketones afforded the alpha-acetoxy ketones in good yield. Selective hydrolysis of the acetoxy ketones by the fungus Rhizopus oryzae yields (R)-hydroxy ketones in high enantiomeric excess. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Chemistry of oxaziridines. 18. Synthesis and enantioselective oxidations of the [(8,8-dihalocamphoryl)sulfonyl]oxaziridines
  作者：Franklin A. Davis、Michael C. Weismiller、Christopher K. Murphy、R. Thimma Reddy、Band Chi Chen

  DOI：10.1021/jo00052a050

  日期：1992.12

  The synthesis and enantioselective oxidations of [(8,8-dihalocamphoryl)sulfonyl]oxaziridines [8,8-dichloro-1,7,7-trimethyl-2'-(phenylsulfonyl)spiro[bicyclo[2.2.1]heptane-2,3'-oxazinidine]] 13 are reported. These reagents are prepared in two steps from the (camphorylsulfonyl)imine 4 by treatment of the corresponding azaenolate with electrophilic halogen sources followed by biphasic oxidation of the resulting dihalo imine 6-9 with m-CPBA/K2CO3. Of these oxaziridines the dichloro reagent 13b, available on a multigram scale, affords the highest enantioselectivities for the asymmetric oxidation of sulfides to sulfoxides (42-74%) and for the hydroxylation of enolates (often better than 95% ee). In general the molecular recognition is predicted and explained in terms of minimization of nonbonded steric interactions the transition states. For the asymmetric oxidation of sulfides to sulfoxides, secondary electronic factors related to the polarity of the sulfide and oxaziridine also play a role. Definitive evidence for chelation of the metal enolate with the C-X bond in 13 is not found. The molecular recognition is interpreted in terms of the higher reactivity of the reagents and an active-site structure which is sterically complementary with the enolate. For the asymmetric hydroxylation of the Z- and E-enolates of propiophenone (16a), the Z-enolate exhibits much higher stereoselectivity than the E-enolate: >95% vs 22% ee.