9-(1-Phenyl-4-hydroxypiperidin-4-yl)-3,3-dimethyl-1,5-dioxaspiro[5.5]undecane-9-carboxylic acid | 299158-67-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 9-(1-Phenyl-4-hydroxypiperidin-4-yl)-3,3-dimethyl-1,5-dioxaspiro[5.5]undecane-9-carboxylic acid
• CAS: 299158-67-1
• 化学式: C₂₃H₃₃NO₅
• 分子量: 403.519
• InChiKey: DLPSMTANKTYKKM-UHFFFAOYSA-N

物化性质

• 沸点：
  576.4±50.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.43
• 重原子数：
  29.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  79.23
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  9-(1-Phenyl-4-hydroxypiperidin-4-yl)-3,3-dimethyl-1,5-dioxaspiro[5.5]undecane-9-carboxylic acid 在 10percent Pd/C 盐酸 、 氢气 、 N,N-二甲基甲酰胺二新戊基乙缩醛 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 4.0h， 生成 4-(1-Phenylpiperidin-4-yl)cyclohexanone
  参考文献：
  名称：

  Photoinduced Intramolecular Charge Separation in Donor/Acceptor-Substituted Bicyclohexylidene and Bicyclohexyl

  摘要：

  The photophysical properties of a bicyclohexylidene (1DA) and a bicyclohexyl (2DA) substituted with an anilino electron donor and a dicyanoethylene electron acceptor have been studied. Quenching of local donor emission is observed for these compounds as well as quenching of the "pseudo-local" acceptor emission. Transient absorption spectra show dialkylanilino-type radical-cation and dicyanoethylene-type radical-anion absorptions. These results show that intramolecular charge separation takes place in 1DA and 2DA. This was corroborated by time-resolved microwave conductivity measurements from which large excited-state dipole moments were found for both 1DA and 2DA. Time-resolved fluorescence spectroscopy revealed that in the charge-separated state in cyclohexane for 2DA, molecular folding takes place on a nanosecond timescale. For 1DA in cyclohexane, either charge separation takes place in a (fully) folded conformation or very rapid (subnanosecond timescale) folding takes place subsequent to charge separation. In addition to this difference in conformational behavior, the presence of the exocyclic double bond between the cyclohexyl-type rings results in efficient quenching of the anilino donor triplet state and acceleration of the charge recombination rate by a factor of 20.

  DOI：

  10.1002/1521-3765(20000818)6:16<2948::aid-chem2948>3.0.co;2-0
• 作为产物：
  描述：

  1-苯基-4-哌啶酮 、 3,3-二甲基-1,5-二氧杂螺[5.5]十一烷-9-羧酸 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.0h， 以36%的产率得到9-(1-Phenyl-4-hydroxypiperidin-4-yl)-3,3-dimethyl-1,5-dioxaspiro[5.5]undecane-9-carboxylic acid
  参考文献：
  名称：

  Photoinduced Intramolecular Charge Separation in Donor/Acceptor-Substituted Bicyclohexylidene and Bicyclohexyl

  摘要：

  The photophysical properties of a bicyclohexylidene (1DA) and a bicyclohexyl (2DA) substituted with an anilino electron donor and a dicyanoethylene electron acceptor have been studied. Quenching of local donor emission is observed for these compounds as well as quenching of the "pseudo-local" acceptor emission. Transient absorption spectra show dialkylanilino-type radical-cation and dicyanoethylene-type radical-anion absorptions. These results show that intramolecular charge separation takes place in 1DA and 2DA. This was corroborated by time-resolved microwave conductivity measurements from which large excited-state dipole moments were found for both 1DA and 2DA. Time-resolved fluorescence spectroscopy revealed that in the charge-separated state in cyclohexane for 2DA, molecular folding takes place on a nanosecond timescale. For 1DA in cyclohexane, either charge separation takes place in a (fully) folded conformation or very rapid (subnanosecond timescale) folding takes place subsequent to charge separation. In addition to this difference in conformational behavior, the presence of the exocyclic double bond between the cyclohexyl-type rings results in efficient quenching of the anilino donor triplet state and acceleration of the charge recombination rate by a factor of 20.

  DOI：

  10.1002/1521-3765(20000818)6:16<2948::aid-chem2948>3.0.co;2-0