5-胆甾烯-3beta-醇 3-巴豆酸酯 | 24951-77-7

• 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
• 中文名称: 5-胆甾烯-3beta-醇 3-巴豆酸酯
• 中文别名: 5-胆甾烯-3beta-醇3-巴豆酸酯
• 英文名称: cholesteryl crotonate
• 英文别名: cholesterylcrotonate；[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] but-2-enoate
• CAS: 24951-77-7
• 化学式: C₃₁H₅₀O₂
• 分子量: 454.737
• InChiKey: WAPKZPLWLMQRHV-GTPODGLVSA-N

物化性质

• 沸点：
  520.4±29.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.52
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  维生素 A 醋酸酯 、 5-胆甾烯-3beta-醇 3-巴豆酸酯 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 甲苯 为溶剂， 反应 96.0h， 生成 cholesteryl (11Z)-13-apo-β-caroten-13-oate 、 cholesteryl (all E)-13-apo-β-caroten-13-oate
  参考文献：
  名称：

  Cross metathesis approach to retinoids and other β-apocarotenoids

  摘要：

  Cross metathesis (CM) reactions between polyenes, such as beta-carotene, canthaxanthin or retinyl acetate, and various alkenes or dienes in the presence of second generation Hoveyda-Grubbs (H II) or Grubbs (G II) catalysts were investigated. Depending on the cross partner different apocarotenoids were obtained. Cross metathesis reactions of retinyl acetate proved to be fully regioselective. Carotenoid CM reactions afforded mixtures of two products due to competing cleavage of the C11-C12 and C15-C15' double bonds. However, regioselectivity can be controlled by choice of appropriate reaction conditions. The reactions of polyenes with dienes worked better in respect of yields and diastereoselectivities than those with monounsaturated cross partners. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.086
• 作为产物：
  描述：

  胆固醇 、 巴豆酰氯 在 三乙胺 、 对苯二酚 作用下， 以 丁酮 为溶剂， 以86%的产率得到5-胆甾烯-3beta-醇 3-巴豆酸酯
  参考文献：
  名称：

  Synthesis of Novel Liquid Crystalline Polyesters of Cholesterol: Thermal, Electrical Conductivity and Dielectric Properties

  摘要：

  Novel liquid crystalline polyesters of cholesterol, Polycholesteryl-3,3-dimethylacrylate (PCHDMA) and Polycholesterylcrotonate (PCHC) are synthesized by free radical polymerization and characterized by FT-IR, H-1-NMR, and GPC analysis. The thermal properties are studied by TGA and DSC techniques. The liquid crystalline phases are detected under hot stage optical microscope. Electronic conduction in the polymers is determined by Wagner polarization technique. There is about 5000 fold decrease in the impedance values of both PCHDMA and PCHC on increasing the frequencies from 40 Hz to 1 MHz at 30 degrees C. Amperometric analysis of the polymers are also carried out at different temperatures and frequencies.

  DOI：

  10.1080/15421406.2014.990681