(2S,3'R)-3'-(4-fluorophenyl)-3,4-dihydro-1H-spiro[naphthalene-2,2'-oxiran]-1-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (2S,3'R)-3'-(4-fluorophenyl)-3,4-dihydro-1H-spiro[naphthalene-2,2'-oxiran]-1-one
• 英文别名: 3'-(4-fluorophenyl)-3,4-dihydro-1H-spiro[naphthalene-2,2'-oxiran]-1-one；(2S,3'R)-3'-(4-fluorophenyl)spiro[3,4-dihydronaphthalene-2,2'-oxirane]-1-one
• 化学式: C₁₇H₁₃FO₂
• 分子量: 268.287
• InChiKey: AOJSZYRQBJDUAE-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  29.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(4-fluorobenzylidene)-3,4-dihydronaphthalen-1(2H)-one 在 叔丁基过氧化氢 、 [(Me₃Si)₂N]₃Yb(μ-Cl)Li(THF)₃ 、 (S)-2,4-di-tert-butyl-6-((2-(hydroxydiphenylmethyl)pyrrolidin-1-yl)methyl)phenol 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以99%的产率得到(2S,3'R)-3'-(4-fluorophenyl)-3,4-dihydro-1H-spiro[naphthalene-2,2'-oxiran]-1-one
  参考文献：
  名称：

  Highly Enantioselective Epoxidation of α,β-Unsaturated Ketones Catalyzed by Rare-Earth Amides [(Me₃Si)₂N]₃RE(μ-Cl)Li(THF)₃ with Phenoxy-Functionalized Chiral Prolinols

  摘要：

  A simple and efficient catalytic enantioselective epoxidation of alpha,beta-unsaturated ketones has been successfully developed, which was catalyzed by rare-earth metal amides [(Me3Si)(2)N](3)RE(mu-Cl)Li(THF)(3) (RE = Yb (1), La (2), Sm (3), Y (4), Lu (5)) in the presence of phenoxy-functionalized chiral prolinols at room temperature using tert-butylhydroperoxide (TBHP) as the oxidant. The combination of an Yb-based amide 1 and a chiral proligand (S)-2,4-di-tert-butyl-6-((2-(hydroxydiphenylmethyl)pyrrolidin-1-yl)methyl)phenol) performed very well, and both the yields and the enantiomeric excess of the chiral epoxides reached up to 99% and 99% ee.

  DOI：

  10.1021/acs.orglett.5b00833

文献信息

• Lanthanide complexes combined with chiral salen ligands: application in the enantioselective epoxidation reaction of α,β-unsaturated ketones
  作者：Xuexiu Xia、Chengrong Lu、Bei Zhao、Yingming Yao

  DOI：10.1039/c9ra01529a

  日期：——

  1,2-diphenyl-1,2-ethanediamine) were employed in the enantioselective epoxidation of α,β-unsaturated ketones. It was found that the salen–La complex shows the highest efficiency and enantioselectivity. A relatively broad scope of α,β-unsaturated ketones was investigated, and excellent yields (up to 99%) and moderate to good enantioselectivities (37–87%) of the target molecules were achieved.

  容易获得的镧系酰胺 Ln[N(SiMe 3 ) 2 ] 3 (Ln = Nd ( 1 ), Sm ( 2 ), Eu ( 3 ), Yb ( 4 ), La ( 5 )) 与手性 salen 配体 H 2结合La (( S , S )-N , N'-二- ( 3,5-二取代的亚水杨基)-1,2-环己二胺)和H 2 Lb ( ( S , S ) -N , N'-二-(3,5-二取代-水杨基)-1,2-二苯基-1,2-乙二胺)用于α,β-不饱和酮的对映选择性环氧化。结果发现，salen-La 配合物表现出最高的效率和对映选择性。研究了相对广泛的 α,β-不饱和酮，并实现了目标分子的优异产率（高达 99%）和中等至良好的对映选择性（37-87%）。
• Synthesis and stereochemistry of the epoxides of 2-arylmethylidene-1-tetralones
  作者：Waldemar Adam、Judit Halász、Zsigmond Jámbor、Albert Lévai、Csaba Nemes、Tamás Patonay、Gábor Tóth

  DOI：10.1039/p19960000395

  日期：——

  Oxidation of both the E and Z isomers of the 2-arylmethylidene-1-tetralones 1 by alkaline hydrogen peroxide afforded the spiroepoxides trans-2a-g as sole products in high yields. In contrast, the dimethyldioxirane epoxidation of the E isomers la-g gave the corresponding trans spiroepoxides in good yields, while the Z isomers la,c,e yielded the respective cis spiroepoxides in moderate yields, Epoxidation of(Z)-1a,c,e by m-chloroperoxybenzoic acid yielded ca. 6: 1 mixtures of cis-2a,c,e and trans-2a,c,e spiroepoxides, Separation of the isomeric epoxides was achieved by silica gel chromatography and their structures, relative configurations and stereochemistry were elucidated by NMR spectroscopy.