(R)-2-Hydroxy-1-(6-methoxy-naphthalen-2-yl)-propan-1-one | 146736-68-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-2-Hydroxy-1-(6-methoxy-naphthalen-2-yl)-propan-1-one
• CAS: 146736-68-7
• 化学式: C₁₄H₁₄O₃
• 分子量: 230.263
• InChiKey: WPVJMTCCWVSVIJ-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (R)-2-Hydroxy-1-(6-methoxy-naphthalen-2-yl)-propan-1-one 在 盐酸 、 甲醇 、 sodium hydride 、 三乙胺 作用下， 反应 0.33h， 生成 (S)-(-)-2-Hydroxy-1-(6-methoxy-2-naphthyl)-1-propanone
  参考文献：
  名称：

  Duh, Tsai-Hui; Wang, Yi-Fong; Wu, Ming-Jung, Journal of the Chinese Chemical Society, 1995, vol. 42, # 3, p. 579 - 584

  摘要：

  DOI：
• 作为产物：
  描述：

  6-甲氧基-2-丙酰萘 在 盐酸 、 titanium(IV) tetraethanolate 、 双(三甲基硅烷基)氨基钾 、 三甲氧基磷 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 为溶剂， 反应 5.0h， 生成 (R)-2-Hydroxy-1-(6-methoxy-naphthalen-2-yl)-propan-1-one
  参考文献：
  名称：

  N-叔丁烷亚磺酰基烯胺的重排，用于合成对映体富集的α-羟基酮衍生物。

  摘要：

  用六甲基二硅叠氮化钾（或叔丁醇钾）和三氟甲磺酸甲酯处理手性N-叔丁烷亚砜基酮亚胺，可得到N-甲基化的N-叔丁烷亚砜基烯胺中间体，该中间体经立体选择性[2,3]重排可制得具有优异α-亚磺酰氧基酮的化合物对映体。这种级联的N-甲基化重排反应甚至被用于生成带有两个α-取代基的无环叔α-羟基酮，这些α-取代基的体积差异可忽略不计，例如甲基和乙基。

  DOI：

  10.1021/acs.orglett.9b03159

文献信息

• Enzymes in organic synthesis: Lipase catalyzed resolution of secondary α-ketoalcohols
  作者：Tsai-Hui Duh、Yi-Fong Wang、Ming-Jung Wu

  DOI：10.1016/s0957-4166(00)80419-x

  日期：1993.8

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