(Z)-3-hexenyl lithocholate | 876928-62-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (Z)-3-hexenyl lithocholate
• CAS: 876928-62-0
• 化学式: C₃₀H₅₀O₃
• 分子量: 458.725
• InChiKey: UQBCIUBGYQQIDO-IWOVBIBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.32
• 重原子数：
  33.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (Z)-3-hexenyl lithocholate 在 溶剂黄146 、 间氯过氧苯甲酸 、 sodium iodide 作用下， 以 四氢呋喃 、 氯仿 、 丙酮 为溶剂， 反应 72.0h， 生成 4-oxohexyl lithocholate
  参考文献：
  名称：

  霍霍巴链长对液体蜡化学反应性的缓和作用

  摘要：

  AbstractJojoba wax and its derivatives are slow‐reacting compounds. To elucidate the reasons for this phenomenon, we reacted jojoba mono‐ and bis‐epoxide and trans‐jojoba bis‐epoxide (C38–C44 long‐chain esters), as well as side chain esters of three steroid skeleton mono‐epoxide derivatives with NaI under acidic conditions to yield the corresponding iodohydrins, which then formed the respective bis‐keto (or mono‐ketone) derivatives. The kinetics, activation energies, and thermodynamic parameters of activation of nucleophilic epoxide opening and pinacol rearrangement were determined for all these compounds. The reaction rates of the jojoba derivatives were similar to those of two of the epoxides derived from the steroid skeleton compounds, and in the third case the steroid derivative reacted somewhat faster than all the rest. This pattern of rate retardation could stem either from folding of the long jojoba chain, resulting in steric hindrance around the reaction centers, or from repeated unproductive collisions along the long hydrocarbon chain of the jojoba wax (statistical effect). Our results appear to suggest that the multiple unsuccessful collisions were the dominant factor, although steric hindrance cannot be ruled out.

  DOI：

  10.1007/s11746-005-1080-7
• 作为产物：
  描述：

  叶醇 、 石胆酸 在 硫酸 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以61%的产率得到(Z)-3-hexenyl lithocholate
  参考文献：
  名称：

  霍霍巴链长对液体蜡化学反应性的缓和作用

  摘要：

  AbstractJojoba wax and its derivatives are slow‐reacting compounds. To elucidate the reasons for this phenomenon, we reacted jojoba mono‐ and bis‐epoxide and trans‐jojoba bis‐epoxide (C38–C44 long‐chain esters), as well as side chain esters of three steroid skeleton mono‐epoxide derivatives with NaI under acidic conditions to yield the corresponding iodohydrins, which then formed the respective bis‐keto (or mono‐ketone) derivatives. The kinetics, activation energies, and thermodynamic parameters of activation of nucleophilic epoxide opening and pinacol rearrangement were determined for all these compounds. The reaction rates of the jojoba derivatives were similar to those of two of the epoxides derived from the steroid skeleton compounds, and in the third case the steroid derivative reacted somewhat faster than all the rest. This pattern of rate retardation could stem either from folding of the long jojoba chain, resulting in steric hindrance around the reaction centers, or from repeated unproductive collisions along the long hydrocarbon chain of the jojoba wax (statistical effect). Our results appear to suggest that the multiple unsuccessful collisions were the dominant factor, although steric hindrance cannot be ruled out.

  DOI：

  10.1007/s11746-005-1080-7