cholesteryl decyl ether | 13131-69-6

• 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: cholesteryl decyl ether
• 英文别名: decyl cholesteryl ether；3-decylcholesterol；(3S,8S,9S,10R,13R,14S,17R)-3-decoxy-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]phenanthrene
• CAS: 13131-69-6
• 化学式: C₃₇H₆₆O
• 分子量: 526.93
• InChiKey: FBZUULDOYSLMAS-FLRGOTCDSA-N

物化性质

• 沸点：
  578.2±29.0 °C(Predicted)
• 密度：
  0.93±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  13.6
• 重原子数：
  38
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  cholesteryl decyl ether 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以82.5%的产率得到5α,6α-epoxy-3-decylcholesterol
  参考文献：
  名称：

  Synthesis and characterisation of new types of side chain cholesteryl polymers

  摘要：

  A series of cholesterol derivatives have been synthesised via the alkylation reaction of the 3-hydroxyl group with the aliphatic bromide compounds with different chain lengths. namely 3 beta-alkyloxy-cholesterol. The double bond between the C5 and C6 positions in these cholesterol derivatives was oxidised into epoxy, followed by an epoxy-ring-opening reaction with the treatment with acrylic acid, resulting in a series of 3 beta-alkyloxy-5 alpha-hydroxy-6 beta-acryloyloxycholesterol, C(n)OCh (n = 1, 2, 4, 6, 8, 10, 12), The acrylate group is connected to the C6 position, which is confirmed by the single crystal structure analysis. The corresponding polymers, PC(n)OCh, were prepared via free radical polymerisation. The structure of monomers and the resulting polymers were characterised with nuclear magnetic resonance (NMR), Fourier transform infrared spectroscopy (FT-IR) and gel permeation chromatography (GPC). The thermal properties of PC(n)OCh were studied using differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA). To determine the secondary structure of polymers, circular dichroism (CD) spectra were performed. It was found that not all monomers produce high-molecular-weight polymers because of steric hindrance. However, all polymers have a helical structure, which can be enhanced by increasing the alkoxy chain length. In addition, increasing the alkoxy chain length decreases the glass transition temperature and increases the decomposition temperature of the polymers. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2010.10.011
• 作为产物：
  描述：

  癸基溴 、 胆固醇 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以64.5%的产率得到cholesteryl decyl ether
  参考文献：
  名称：

  Synthesis and characterisation of new types of side chain cholesteryl polymers

  摘要：

  A series of cholesterol derivatives have been synthesised via the alkylation reaction of the 3-hydroxyl group with the aliphatic bromide compounds with different chain lengths. namely 3 beta-alkyloxy-cholesterol. The double bond between the C5 and C6 positions in these cholesterol derivatives was oxidised into epoxy, followed by an epoxy-ring-opening reaction with the treatment with acrylic acid, resulting in a series of 3 beta-alkyloxy-5 alpha-hydroxy-6 beta-acryloyloxycholesterol, C(n)OCh (n = 1, 2, 4, 6, 8, 10, 12), The acrylate group is connected to the C6 position, which is confirmed by the single crystal structure analysis. The corresponding polymers, PC(n)OCh, were prepared via free radical polymerisation. The structure of monomers and the resulting polymers were characterised with nuclear magnetic resonance (NMR), Fourier transform infrared spectroscopy (FT-IR) and gel permeation chromatography (GPC). The thermal properties of PC(n)OCh were studied using differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA). To determine the secondary structure of polymers, circular dichroism (CD) spectra were performed. It was found that not all monomers produce high-molecular-weight polymers because of steric hindrance. However, all polymers have a helical structure, which can be enhanced by increasing the alkoxy chain length. In addition, increasing the alkoxy chain length decreases the glass transition temperature and increases the decomposition temperature of the polymers. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2010.10.011

文献信息

• Montmorillonite Clay Catalysis. Part 13.1 Etherification of Cholesterol Catalysed by Montmorillonite K-10
  作者：Bo Lu、Li-Jun Li、Tong-Shuang Li、Ji-Tai Li

  DOI：10.1039/a803050b

  日期：——

  The preparation of cholesteryl ethers from alcohols and phenols with cholesterol is carried out at 50–70°C by using montmorillonite K-10 as an acid catalyst in chloroform or cyclohexane.

  使用蒙脱石K-10作为酸催化剂，在氯仿或环己烷中于50-70°C下进行醇和酚与胆固醇制备胆固醇醚的反应。
• The synthesis of cholesteryl alkyl ethers
  作者：G. Halperin、S. Gatt

  DOI：10.1016/0039-128x(80)90109-9

  日期：1980.1

  Seventeen cholesteryl alkyl ethers were synthesized through alcoholysis of cholesterol p-toluenesulfonate. This method was found superior to the etherification of sodium or potassium cholesterylate with alkyl halides or methanesulfonates, especially for the preparation of long-chain unsaturated aklyl ethers of [7(m)-3H]cholesterol of high specific activity.

  通过胆固醇对甲苯磺酸的醇解合成了十七种胆固醇烷基醚。发现该方法优于胆甾醇钠或胆甾醇钾与烷基卤化物或甲磺酸盐的醚化，特别是用于制备高比活性的 [7(m)-3H] 胆固醇的长链不饱和烷基醚。
• Synthesis and characterisation of new types of side chain cholesteryl polymers
  作者：Bin Wang、Haiyan Du、Junhua Zhang

  DOI：10.1016/j.steroids.2010.10.011

  日期：2011.1

  A series of cholesterol derivatives have been synthesised via the alkylation reaction of the 3-hydroxyl group with the aliphatic bromide compounds with different chain lengths. namely 3 beta-alkyloxy-cholesterol. The double bond between the C5 and C6 positions in these cholesterol derivatives was oxidised into epoxy, followed by an epoxy-ring-opening reaction with the treatment with acrylic acid, resulting in a series of 3 beta-alkyloxy-5 alpha-hydroxy-6 beta-acryloyloxycholesterol, C(n)OCh (n = 1, 2, 4, 6, 8, 10, 12), The acrylate group is connected to the C6 position, which is confirmed by the single crystal structure analysis. The corresponding polymers, PC(n)OCh, were prepared via free radical polymerisation. The structure of monomers and the resulting polymers were characterised with nuclear magnetic resonance (NMR), Fourier transform infrared spectroscopy (FT-IR) and gel permeation chromatography (GPC). The thermal properties of PC(n)OCh were studied using differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA). To determine the secondary structure of polymers, circular dichroism (CD) spectra were performed. It was found that not all monomers produce high-molecular-weight polymers because of steric hindrance. However, all polymers have a helical structure, which can be enhanced by increasing the alkoxy chain length. In addition, increasing the alkoxy chain length decreases the glass transition temperature and increases the decomposition temperature of the polymers. (C) 2010 Elsevier Inc. All rights reserved.