3,3-Bis(4-bromophenylsulfanyl)-1-methylpiperidin-2-one | 1448012-87-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3,3-Bis(4-bromophenylsulfanyl)-1-methylpiperidin-2-one
• 英文别名: 3,3-bis[(4-bromophenyl)sulfanyl]-1-methylpiperidin-2-one
• CAS: 1448012-87-0
• 化学式: C₁₈H₁₇Br₂NOS₂
• 分子量: 487.279
• InChiKey: XTTBIHKEHSCAOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  70.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-甲基-2-哌啶酮 、 4-二溴苯基二硫化物 在 六甲基磷酰三胺 、 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.33h， 以0.4 g的产率得到3,3-Bis(4-bromophenylsulfanyl)-1-methylpiperidin-2-one
  参考文献：
  名称：

  Conformational preferences for some 3,3-bis[(4′-substituted phenylsulfanyl)]1-methyl-2-piperidinones through spectroscopic and theoretical studies

  摘要：

  The analysis of the IR carbonyl band of some 3,3-bis[(4'-substituted phenylsulfanyl)]1-methyl-2-piperidinones 1-5 bearing as substituentsOMe1, Me2, H3, Cl4 and Br5, supported by B3LYP/6-31G(d,p) calculations for 3, indicated the existence of three conformers in the gas phase and practically a single conformer in solution. In the gas phase, the c(1) conformer is less polar and slightly more stable than the most polar c(2) conformer. The c(3) conformer is the least polar and least stable conformer. The summing up of the selected natural bond orbital delocalization orbital energies is practically the same (ca.136 kcal mol(-1)) for the c(1), c(2) and c(3) conformers of 3. Therefore, the trend of the [O delta- (CO)(center dot center dot center dot H delta+) o-Ph] (hydrogen bond) attractive electrostatic interactions along with the trend of the [O delta- (CO)S-center dot center dot center dot(delta-)] repulsive electrostatic interactions are the main factors which determine the observed computed relative populations for the c(1) (44%), c(2) (31%) and c(3) (25%) conformers. Moreover, the IR single carbonyl stretching band found (for 1-5) in solvents of increasing relative permissivity (CCl4, CHCl3, CH2Cl2, CH3CN), in agreement with polarisable continuum model calculations (for 3), show that the most polar c(2) conformer is practically unique in the solution (for 1-5), and the geometry is very close to that of the c(2') conformer in the solid state (for 1-4).[GRAPHICS].

  DOI：

  10.1080/17415993.2013.771359

文献信息

• Conformational preferences for some 3,3-bis[(4′-substituted phenylsulfanyl)]1-methyl-2-piperidinones through spectroscopic and theoretical studies
  作者：Paulo R. Olivato、Carlos R. Cerqueira Jr、Bruna Contieri、Jean M. M. Santos、Julio Zukerman-Schpector

  DOI：10.1080/17415993.2013.771359

  日期：2013.12.1

  The analysis of the IR carbonyl band of some 3,3-bis[(4'-substituted phenylsulfanyl)]1-methyl-2-piperidinones 1-5 bearing as substituentsOMe1, Me2, H3, Cl4 and Br5, supported by B3LYP/6-31G(d,p) calculations for 3, indicated the existence of three conformers in the gas phase and practically a single conformer in solution. In the gas phase, the c(1) conformer is less polar and slightly more stable than the most polar c(2) conformer. The c(3) conformer is the least polar and least stable conformer. The summing up of the selected natural bond orbital delocalization orbital energies is practically the same (ca.136 kcal mol(-1)) for the c(1), c(2) and c(3) conformers of 3. Therefore, the trend of the [O delta- (CO)(center dot center dot center dot H delta+) o-Ph] (hydrogen bond) attractive electrostatic interactions along with the trend of the [O delta- (CO)S-center dot center dot center dot(delta-)] repulsive electrostatic interactions are the main factors which determine the observed computed relative populations for the c(1) (44%), c(2) (31%) and c(3) (25%) conformers. Moreover, the IR single carbonyl stretching band found (for 1-5) in solvents of increasing relative permissivity (CCl4, CHCl3, CH2Cl2, CH3CN), in agreement with polarisable continuum model calculations (for 3), show that the most polar c(2) conformer is practically unique in the solution (for 1-5), and the geometry is very close to that of the c(2') conformer in the solid state (for 1-4).[GRAPHICS].