5α-cholestan-3-yliden-acetic acid ethyl ester | 2537-47-5

• 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: 5α-cholestan-3-yliden-acetic acid ethyl ester
• 英文别名: 5α-Cholestan-3-yliden-essigsaeure-aethylester；ethyl 2-[(5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-ylidene]acetate
• CAS: 2537-47-5
• 化学式: C₃₁H₅₂O₂
• 分子量: 456.753
• InChiKey: QCIADEIKEKPUMO-GTPODGLVSA-N

物化性质

• 熔点：
  83-85 °C
• 沸点：
  520.5±19.0 °C(Predicted)
• 密度：
  0.986±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  5α-cholestan-3-yliden-acetic acid ethyl ester 在 platinum(IV) oxide 氢气 作用下， 反应 3.0h， 以99%的产率得到(5α)-3-Ethoxycarbonylmethylcholestane
  参考文献：
  名称：

  Lipophilic bis-arylsulfonates as inhibitors of the CD4-gp120 interaction

  摘要：

  A series of lipophilic bis-arylsulfonates was synthesized and evaluated as potential inhibitors of the CD4-gp120 interaction. Structure-activity studies suggested a direct relationship between the nature and extent of lipophilicity and inhibitory potency. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00552-5
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 硫酸 、 Petroleum ether 作用下， 生成 5α-cholestan-3-yliden-acetic acid ethyl ester
  参考文献：
  名称：

  Studies in the Synthesis of the Antirachitic Vitamins. VI. The Synthesis of 2-Cholestanylidene-ethan-1-al

  摘要：

  DOI：

  10.1021/ja01542a039

文献信息

• Microwave Accelerated Wittig Reactions of Stabilized Phosphorus Ylides with Ketones under Solvent-Free Conditions
  作者：Aldo Spinella、Tancredi Fortunati、Annunziata Soriente

  DOI：10.1055/s-1997-689

  日期：——

  Microwave irradiation accelerates some difficult Wittig reactions of stable phosphorus ylides (e.g. 1) with ketones. Irradiation in a domestic microwave oven of the mixture of reactants, in absence of solvents, allowed to obtain, in shorter times, an improvement of transformation yields over conventional heating method.

  微波辐射加速了稳定磷叶立德（例如1）与酮类在某些困难Wittig反应中的反应速度。在无溶剂条件下，将反应物混合置于家用微波炉中照射，能够在更短的时间内获得比传统加热方法更高的转化产率。
• Pd-Catalyzed Formal [3 + 3] Heteroannulation of Allylic <i>gem</i>-Diacetates: Synthesis of Chromene-Based Natural Products and Exploration of Photochromic Properties
  作者：Prashant Kumar、Pravesh Kumar、Sugumar Venkataramani、S. S. V. Ramasastry

  DOI：10.1021/acscatal.1c05450

  日期：2022.1.21

  meta-substituted phenols) to produce novel polycyclic chromenes possessing spiro-, tri-, and tetrasubstituted carbon centers. The versatility of the method is demonstrated in the synthesis of several chromene-based bioactive natural products. Further, interesting photochromic properties of the new classes of benzo[f]chromenes are also discovered.

  很少探索钯催化的烯丙基偕二乙酸酯的烯丙基烷基化反应。这项工作揭示了烯丙基宝石-二乙酸酯的一种不寻常的化学反应模式，并将它们确立为合成复杂苯并[ f ]色烯系统的新原型。在反应条件下，二乙酸酯表现为 1,3-双阳离子等价物，并与 2-萘酚（和间位取代的酚）发生 [3 + 3] 杂环化反应，生成具有螺、三和四取代碳的新型多环色烯中心。该方法的多功能性在几种基于色烯的生物活性天然产物的合成中得到证明。此外，新类别苯并[ f]铬烯也被发现。
• Photocatalyzed, β-Selective Hydrocarboxylation of α,β-Unsaturated Esters with CO₂ under Flow for β-Lactone Synthesis
  作者：Guowei Kang、Daniel Romo

  DOI：10.1021/acscatal.0c05050

  日期：2021.2.5

  photocatalyzed, β-selective hydrocarboxylation of α,β-unsaturated esters employing CO2 radical anion generated under flow conditions was developed. A range of substrates bearing a variety of functional groups were tolerated, demonstrating chemoselectivity. A series of quaternary carboxylic acids were obtained from sterically demanding β,β-disubstituted alkenes including those derived from natural products. Mechanistic

  利用流动条件下产生的CO 2自由基阴离子，开发了α，β-不饱和酯的光催化β-选择性加氢羧化反应。耐受各种带有各种官能团的底物，证明了其化学选择性。从空间上需要的β，β-二取代的烯烃（包括那些衍生自天然产物的烯烃）获得了一系列季羧酸。机理研究支持添加Giese型CO 2自由基阴离子共轭物，然后从（TMS）3 SiH转移氢原子作为主要反应途径。最后，涉及所述β-羧化然后是α-溴化/β-内酯化序列的伸缩过程提供了β-内酯合成的策略。