9-((S)-Methanesulfinyl)-anthracene | 89616-63-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9-((S)-Methanesulfinyl)-anthracene
• 英文别名: 9-[(S)-methylsulfinyl]anthracene
• CAS: 89616-63-7
• 化学式: C₁₅H₁₂OS
• 分子量: 240.326
• InChiKey: TZRRMGZVXZEKCT-KRWDZBQOSA-N

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

• 作为产物：
  描述：

  9-(methylthio)anthracene 在 (3'S,2R)-(-)-N-(phenylsulfonyl)(3,3-dichlorocamphoryl)oxaziridine 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (R)-methyl 9-anthrylsulfoxide 、 9-((S)-Methanesulfinyl)-anthracene
  参考文献：
  名称：

  氧氮杂环丙烷化学。17. N-(Phenylsulfonyl)(3,3-dichlorocamphoryl)oxaziridine：一种将硫化物不对称氧化成亚砜的高效试剂

  摘要：

  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

  DOI：

  10.1021/ja00030a045

文献信息

• (-)-.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
• 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.
• DAVIS, FRANKLIN;REDDY, R. THIMMA;MCCAULEY, JOHN P. (JR);PRZESLAWSKI, ROBE+, J. ORG. CHEM., 56,(1991) N, C. 809-815
  作者：DAVIS, FRANKLIN、REDDY, R. THIMMA、MCCAULEY, JOHN P. (JR)、PRZESLAWSKI, ROBE+

  DOI：——

  日期：——
• DEVIS, F. A.;MCCAULEY, J. P. ,, JR;HARAKAL, M. E., J. ORG. CHEM., 1984, 49, N 8, 1465-1467
  作者：DEVIS, F. A.、MCCAULEY, J. P. ,, JR、HARAKAL, M. E.

  DOI：——

  日期：——