氯乙酸胆固醇 | 3464-50-4

• 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: 氯乙酸胆固醇
• 英文名称: chloroacetic acid cholesterylester
• 英文别名: cholesteryl chloroacetate；chloroacetic acid 17-(1,5-dimethylhexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester；cholesteryl 2-chloroacetate；(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl 2-chloroacetate；Cholesterol chloroacetate；[(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] 2-chloroacetate
• CAS: 3464-50-4
• 化学式: C₂₉H₄₇ClO₂
• 分子量: 463.144
• InChiKey: XUXXPLDKUZSGKH-OHPSOFBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.896
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  氯乙酸胆固醇 在 溴 作用下， 以 氯仿 为溶剂， 生成 chloroacetic acid-(5,6β-dibromo-5α-cholestanyl-(3β)-ester)
  参考文献：
  名称：

  Maas,S.P.J. et al., Bulletin des Societes Chimiques Belges, 1963, vol. 72, p. 239 - 254

  摘要：

  DOI：
• 作为产物：
  描述：

  胆固醇 、 氯乙酸酐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以97%的产率得到氯乙酸胆固醇
  参考文献：
  名称：

  新型无毒单阳离子脂质的合成和转染特性。脂质锚，间隔基和头基结构的变化。

  摘要：

  该报告描述了新型单阳离子无毒脂质的合成和转染特性。我们在转染脂质，脂质锚，间隔基和带正电的头部基团的所有三个单元中进行了结构变异。我们的结果得出结论，系统修饰结构亚基是提高转染效率的一种有前途的方式。

  DOI：

  10.1016/s0960-894x(00)00099-8

文献信息

• Cholesterol appended pyridinium ureas: a case of gel making and breaking for selective visual readout of F−
  作者：Kumaresh Ghosh、Debasis Kar

  DOI：10.1039/c2ob26631h

  日期：——

  Cholesterol appended pyridinium ureas 1 and 2 have been designed and synthesized. The unsymmetrical urea-based chemosensor 1 fluorimetrically distinguishes F− from the other anions examined in both CH3CN and DMSO with appreciable binding constant values. The pyridinium – based symmetrical compound 2 acts as a low molecular weight gelator (LMWG) in CHCl3 and is capable of detecting F− visually by breaking the gel. On the contrary, the chemosensor 1 in DMSO in the presence of tetrabutylammonium fluoride undergoes a change from sol to gel state that produces an unambiguous visual readout of F−.

  设计和合成了胆固醇缀合的吡啶鎓脲1和2。基于不对称脲的化学传感器1能通过荧光差异性区分F⁻与在CH₃CN和DMSO中的其他所检测阴离子，且结合常数值良好。基于吡啶鎓的对称化合物2在CHCl₃中作为一种低分子量凝胶剂(LMWG)，并能通过破坏凝胶实现对F⁻的视觉检测。相反，在DMSO中含四丁基氟化铵时，化学传感器1经历从溶解态到凝胶态的变化，从而产生F⁻的确切视觉指示。
• Cholesterol-Appended Benzimidazolium Salts: Synthesis, Aggregation, Sensing, Dye Adsorption, and Semiconducting Properties
  作者：Santanu Panja、Subhratanu Bhattacharya、Kumaresh Ghosh

  DOI：10.1021/acs.langmuir.7b01713

  日期：2017.8.22

  A series of cholesterol-appended benzimidazolium salts 1–9 have been designed and synthesized. They have been explored in gel chemistry. The gelation of the benzimidazolium salts is dependent on the nature of the counteranions. In addition, the gelation behavior of the gelators is linked with the presence of both π-stacking and cholesteryl motifs. Whereas bisbenzimidazolium salt 2 forms a gel in d

  已经设计并合成了一系列胆固醇附加的苯并咪唑鎓盐1–9。他们已经在凝胶化学中进行了探索。苯并咪唑盐的凝胶化取决于抗衡阴离子的性质。另外，胶凝剂的胶凝行为与π-堆积和胆固醇基序的存在有关。而bisbenzimidazolium盐2所形成的凝胶在二甲亚砜/ H 2 O（1：1，V / V）本身，在类似条件下，monobenzimidazolium盐4和6表现出凝胶化在F的存在-离子和验证F的视觉传感-。作为应用，凝胶相为2有效去除废水中的有毒染料。此外，所有凝胶均在较宽的电压范围内显示出热活化的半导体特性。
• Cholesterol appended bis-1,2,3-triazoles as simple supramolecular gelators for the naked eye detection of Ag⁺, Cu²⁺ and Hg²⁺ ions
  作者：Kumaresh Ghosh、Atanu Panja、Santanu Panja

  DOI：10.1039/c5nj02771c

  日期：——

  Cholesterol coupled bis-1,2,3-triazoles have been designed and synthesized. Their gelation abilities and cation responsive behaviors are documented.

  胆固醇偶联的双-1,2,3-三唑已被设计并合成。它们的凝胶能力和阳离子响应行为已记录。
• Diaminomalenonitrile-decorated cholesterol-based supramolecular gelator: aggregation, multiple analyte (hydrazine, Hg²⁺ and Cu²⁺) detection and dye adsorption
  作者：Atanu Panja、Kumaresh Ghosh

  DOI：10.1039/c8nj02426j

  日期：——

  A low molecular weight gelator (LMWG) containing a diaminomalenonitrile functional group 1 forms supramolecular gels from DMF–H₂O and 1,2-dichlorobenzene. The DMF/H₂O gel is multi-analyte responsive (Hg²⁺, Cu²⁺ and hydrazine) with practical applications in dye adsorption from water.

  一种含有二氨基马来腈官能团的低分子量凝胶剂（LMWG）1能够从DMF–H₂O和1,2-二氯苯中形成超分子凝胶。DMF/H₂O凝胶对多种分析物具有响应性（Hg²⁺、Cu²⁺和叠氮化物），在水中染料吸附方面具有实际应用。
• A sulfonyl hydrazone cholesterol conjugate: gelation, anion interaction and its application in dye adsorption
  作者：Atanu Panja、Sumit Ghosh、Kumaresh Ghosh

  DOI：10.1039/c8nj05613g

  日期：——

  Cholesterol appended sulfonyl-hydrazone derivative 1 was designed and synthesized as a supramolecular gelator for anionic sensing and dye adsorption. Gelator 1 forms a strong gel in DMSO–H₂O and the morphology of the xerogel shows a tiny rod-like fibrous network. The gel of 1 shows a selective response toward CN⁻ and F⁻ ions causing gel-to-sol transformation. The gel of 1 acts as an efficient matrix for adsorption and removal of anionic dyes such as erythrosine B and uranine from water.

  胆固醇附加的磺酰基腙衍生物1被设计并合成为一种用于阴离子传感和染料吸附的超分子凝胶剂。凝胶剂1在DMSO-H2O中形成强凝胶，干凝胶的形态显示出微小的类似棒状的纤维网络。凝胶1对CN-和F-离子显示出选择性响应，导致凝胶向溶胶的转变。凝胶1作为吸附和去除水中类似红色素B和尿兰的阴离子染料的高效基质。

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