cholest-5-en-3β-yl 5-carboxypentyl ether | 103024-61-9

• 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: cholest-5-en-3β-yl 5-carboxypentyl ether
• CAS: 103024-61-9
• 化学式: C₃₃H₅₆O₃
• 分子量: 500.806
• InChiKey: QPVIJNPPVIELGB-FLFWOSPYSA-N

物化性质

• 沸点：
  594.3±43.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.06
• 重原子数：
  36.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-羟基丁二酰亚胺 、 cholest-5-en-3β-yl 5-carboxypentyl ether 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (2,5-dioxopyrrolidin-1-yl) 6-[[(3S,10R,13R,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]oxy]hexanoate
  参考文献：
  名称：

  Functional cholesteryl binding agents: synthesis, characterization, and evaluation of antibody binding to modified phospholipid vesicles

  摘要：

  A series of functionalized cholesteryl derivatives were synthesized. The various lipophilic protein modification agents were analyzed for their protein binding ability. The binding of human IgG, labeled with 125I, to modified phospholipid vesicles was ascertained. Two agents performed well. These were cholest-5-en-3 beta-yl 5-carboxypentyl ether succinimido ester and cholest-5-en-3 beta-yl 6-carboxyhexyl ether succinimido ester.

  DOI：

  10.1021/jm00160a004
• 作为产物：
  描述：

  [10,13-二甲基-17-(6-甲基庚烷-2-基)-2,3,4,7,8,9,11,12,14,15,16,17-十二氢-1H-环戊并[a]菲-3-基] 4-甲基苯磺酸酯 在 chromium(VI) oxide 、 硫酸 作用下， 以 1,4-二氧六环 、 丙酮 为溶剂， 生成 cholest-5-en-3β-yl 5-carboxypentyl ether
  参考文献：
  名称：

  Functional cholesteryl binding agents: synthesis, characterization, and evaluation of antibody binding to modified phospholipid vesicles

  摘要：

  A series of functionalized cholesteryl derivatives were synthesized. The various lipophilic protein modification agents were analyzed for their protein binding ability. The binding of human IgG, labeled with 125I, to modified phospholipid vesicles was ascertained. Two agents performed well. These were cholest-5-en-3 beta-yl 5-carboxypentyl ether succinimido ester and cholest-5-en-3 beta-yl 6-carboxyhexyl ether succinimido ester.

  DOI：

  10.1021/jm00160a004

文献信息

• [3,3]-Acyloxy Rearrangement-Triggered Regioselective Hydration of δ-Acetoxy-α,β-Alkynoates/Halo Alkynes
  作者：Kishor L. Mendhekar、Tapas R. Pradhan、Debendra K. Mohapatra

  DOI：10.1021/acs.joc.0c00061

  日期：2020.4.3

  that is facilitated by an unusual interception of an electrophilic intermediate by water generated via acetate group participation during [3,3]-acyloxy rearrangement. Various carboxylate-directing groups including acetate, acrylates, pivalates, benzoate or its derivatives, and those derived from bioactive natural products were successfully implemented to direct the regioselective hydration for various

  在这里，我们报告了一种简单，有效，高度区域选择性和广谱水合作用的方法，该方法通过[3,3]-酰氧基重排过程中通过乙酸酯基团参与生成的水对亲电子中间体的不寻常拦截而得到促进。成功地实现了包括乙酸酯，丙烯酸酯，新戊酸酯，苯甲酸酯或其衍生物在内的各种羧酸酯导向基团，以及衍生自生物活性天然产物的那些，以指导区域选择性水合用于各种功能化的δ-酰氧基-β-酮酸酯合成。反应路径通过进一步证实18O标记实验，就我们所知，这是通过[3,3]-酰氧基重排过程中产生的亲电子中间体水合的第一个报道。合成应用包括可修饰的C5碳链，五元，六元和七元杂环的合成，以及天然产物的多样化。