3,5-bis{{6-[(3β)-cholest-5-en-3-yloxy]hexyl}oxy}benzenemethanol | 358351-56-1

• 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: 3,5-bis{{6-[(3β)-cholest-5-en-3-yloxy]hexyl}oxy}benzenemethanol
• CAS: 358351-56-1
• 化学式: C₇₃H₁₂₀O₅
• 分子量: 1077.75
• InChiKey: HDNJNATWOWPBCQ-ONBJPNOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.91
• 重原子数：
  78.0
• 可旋转键数：
  29.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  propane dioic acid {5-{2-[2-(2-methoxy)ethoxy]ethoxy}-1,3-phenylene}bis(methylene) ester 、 3,5-bis{{6-[(3β)-cholest-5-en-3-yloxy]hexyl}oxy}benzenemethanol 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以85%的产率得到propanedioic acid {5-{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}-1,3-phenylene}bis(methylene) bis{{3,5-bis{{6-[(3β)-cholest-5-en-3-yloxy]hexyl}oxy}phenyl}methyl} ester
  参考文献：
  名称：

  Amphiphilic Fullerene-Cholesterol Derivatives: Synthesis and Preparation ofLangmuir andLangmuir-Blodgett Films

  摘要：

  Amphiphilic fullerene bis-adducts 11 and 14 containing two and four cholesterol moieties, respectively, were prepared starting from the corresponding bis-malonate derivatives. In a systematic study, their spreading behavior at the air-water interface was compared to that of bis-adduct 6 with no polar head-group. Compared to 6, for which some three-dimensional aggregation occurs, the polar head-group in 11 and 14 is responsible for an attractive interaction with the aqueous subphase, forcing the molecules towards the water surface into a two-dimensional arrangement. Even if homogeneous Langmuir films were obtained with both 11 and 14, only the films of 14 show a reversible compression/expansion behavior. This suggests that, by increasing the number of cholesterol subunits, the encapsulation of the C-sphere in its addend is more efficient, thus preventing fullerene-fullerene interactions and aggregation phenomena. The Langmuir films of 11 and 14 were also efficiently transferred onto hydrophilic quartz slides, yielding Langmuir-Blodgett films.

  DOI：

  10.1002/1522-2675(20010516)84:5<1119::aid-hlca1119>3.0.co;2-3
• 作为产物：
  描述：

  cholest-5-en-3β-yl 6-<(p-tolylsulfonyl)oxy>hexyl ether 在 potassium bromide 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 3,5-bis{{6-[(3β)-cholest-5-en-3-yloxy]hexyl}oxy}benzenemethanol
  参考文献：
  名称：

  Amphiphilic Fullerene-Cholesterol Derivatives: Synthesis and Preparation ofLangmuir andLangmuir-Blodgett Films

  摘要：

  Amphiphilic fullerene bis-adducts 11 and 14 containing two and four cholesterol moieties, respectively, were prepared starting from the corresponding bis-malonate derivatives. In a systematic study, their spreading behavior at the air-water interface was compared to that of bis-adduct 6 with no polar head-group. Compared to 6, for which some three-dimensional aggregation occurs, the polar head-group in 11 and 14 is responsible for an attractive interaction with the aqueous subphase, forcing the molecules towards the water surface into a two-dimensional arrangement. Even if homogeneous Langmuir films were obtained with both 11 and 14, only the films of 14 show a reversible compression/expansion behavior. This suggests that, by increasing the number of cholesterol subunits, the encapsulation of the C-sphere in its addend is more efficient, thus preventing fullerene-fullerene interactions and aggregation phenomena. The Langmuir films of 11 and 14 were also efficiently transferred onto hydrophilic quartz slides, yielding Langmuir-Blodgett films.

  DOI：

  10.1002/1522-2675(20010516)84:5<1119::aid-hlca1119>3.0.co;2-3