(R)-methyl 9-anthrylsulfoxide | 89616-64-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: (R)-methyl 9-anthrylsulfoxide
• 英文别名: (R)-9-methanesulfinylanthracene；9-[(R)-methylsulfinyl]anthracene
• CAS: 89616-64-8
• 化学式: C₁₅H₁₂OS
• 分子量: 240.326
• InChiKey: TZRRMGZVXZEKCT-QGZVFWFLSA-N

物化性质

• 沸点：
  480.4±14.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.73
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (R)-methyl 9-anthrylsulfoxide 以 乙腈 为溶剂， 生成 9-methanesulfinylanthracene
  参考文献：
  名称：

  Photophysics and Photostereomutation of Aryl Methyl Sulfoxides¹

  摘要：

  The effect of a methanesulfinyl group on the photophysics of several aromatic chromophores is reported. The spectroscopic singlet and triplet energies are affected only modestly, compared to that parent arenes, but the fluorescence yields fall by at least 1 order of magnitude. Fluorescence lifetimes are short. Fluorescence enhancements are observed on cooling the sulfoxides from room temperature to 77 K. High quantum yields of stereomutation are reduced as the temperature drops. There is not a consistent effect on triplet or phosphorescence yields. It is proposed that these results are consistent with a nonradiative pathway for deactivation of the singlet that results in stereomutation. A modest activation energy of a few kcal/mol is estimated for the photochemical racemization of 1-methanesulfinylpyrene

  DOI：

  10.1021/jo0056141
• 作为产物：
  描述：

  9-(methylthio)anthracene 、 (+)-2-<(S)-N-(α-methylbenzyl)-N-benzylsulfamyl>-3-(4-nitrophenyl)oxaziridine 生成 (R)-methyl 9-anthrylsulfoxide
  参考文献：
  名称：

  DEVIS, F. A.;MCCAULEY, J. P. ,, JR;HARAKAL, M. E., J. ORG. CHEM., 1984, 49, N 8, 1465-1467

  摘要：

  DOI：

文献信息

• Chemistry of oxaziridines. 17. N-(Phenylsulfonyl)(3,3-dichlorocamphoryl)oxaziridine: a highly efficient reagent for the asymmetric oxidation of sulfides to sulfoxides
  作者：Franklin A. Davis、R. Thimma Reddy、Wei Han、Patrick J. Carroll

  DOI：10.1021/ja00030a045

  日期：1992.2

  The synthesis, structure, and enantioselective oxidations of a new chiral N-sulfonyloxaziridine 12c [3,3-dichloro- 1,7,7-trimethyl-2'-(phenylsulfonyl)spiro[bicyclo[2.2.1]heptane-2,3'-oxaziridine]] are reported. This oxidant, which exhibits remarkably high and predictable ee's for the enantioselective oxidation of prochiral sulfides to sulfoxides, is prepared in three steps from (+)- or (-)-camphor

  一种新型手性 N-磺酰氧氮丙啶 12c [3,3-二氯-1,7,7-三甲基-2'-(苯基磺酰基)螺[双环[2.2.1]庚烷-2,3]的合成、结构和对映选择性氧化'-oxaziridine]] 报道。这种氧化剂在将前手性硫化物对映选择性氧化成亚砜方面表现出非常高且可预测的 ee，它是由 (+)- 或 (-)-樟脑以 50% 的总产率通过三个步骤制备的
• (-)-.alpha.,.alpha.-Dichlorocamphorsulfonyloxaziridine: a superior reagent for the asymmetric oxidation of sulfides to sulfoxides
  作者：Franklin A. Davis、R. ThimmaReddy、Michael C. Weismiller

  DOI：10.1021/ja00197a080

  日期：1989.7
• Chemistry of oxaziridines. 8. Asymmetric oxidation of nonfunctionalized sulfides to sulfoxides with high enantioselectivity by 2-sulfamyloxaziridines. Influence of the oxaziridine C-aryl group on the asymmetric induction
  作者：Franklin A. Davis、John P. McCauley、Sankar Chattopadhyay、Mark E. Harakal、James C. Towson、William H. Watson、Iraj Tavanaiepour

  DOI：10.1021/ja00245a030

  日期：1987.5
• Chiral sulfamides: synthesis of optically active 2-sulfamyloxaziridines. High enantioselectivity in the asymmetric oxidation of sulfides to sulfoxides
  作者：Franklin A. Davis、John P. McCauley、Mark E. Harakal

  DOI：10.1021/jo00182a039

  日期：1984.4
• 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.