epi-cholesteryl (S)-2-(3-benzoylphenyl)propionate | 913843-19-3

• 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: epi-cholesteryl (S)-2-(3-benzoylphenyl)propionate
• 英文别名: (S)-ketoprofen-α-cholesterol；[(3R,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] (2S)-2-(3-benzoylphenyl)propanoate
• CAS: 913843-19-3
• 化学式: C₄₃H₅₈O₃
• 分子量: 622.932
• InChiKey: YSTJOGFMWNRZTP-UBWAWFBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.6
• 重原子数：
  46
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  epi-cholesteryl (S)-2-(3-benzoylphenyl)propionate 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  二苯甲酮三重态激发态从胆固醇中提取氢的溶剂效应

  摘要：

  在产物研究中，三重激发的二苯甲酮（BZP）从胆固醇（Ch）的C-7位置提取氢表现出显着的溶剂依赖性。在含有共价连接的Ch和BZP单元的二元组中，分子内版本过程的动力学测量显示出重要的溶剂作用和显着的立体分化。

  DOI：

  10.1021/ol2016059
• 作为产物：
  描述：

  Chloro-acetic acid (8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-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 在 甲醇 、 potassium carbonate 作用下， 反应 1.0h， 生成 epi-cholesteryl (S)-2-(3-benzoylphenyl)propionate
  参考文献：
  名称：

  Efficient and Selective Photogeneration of Cholesterol-Derived Radicals by Intramolecular Hydrogen Abstraction in Model Dyads

  摘要：

  [GRAPHICS]Three model dyads have been synthesized by esterification of beta- and alpha-cholesterol (Ch) with (S)- and/or (R)-ketoprofen (Kp). The alpha-dyads are efficient photogenerators of the 7-allyl Ch radicals by intramolecular H abstraction. Subsequent cyclization via C-C coupling occurs in a stereoselective way.

  DOI：

  10.1021/ol061854c

文献信息

• Cholesterol–diaryl ketone stereoisomeric dyads as models for “clean” type I and type II photooxygenation mechanisms
  作者：Inmaculada Andreu、Isabel M. Morera、Francisco Boscá、Laura Sanchez、Pelayo Camps、Miguel A. Miranda

  DOI：10.1039/b718068c

  日期：——

  Cholesterol (Ch) is a major target for oxidative degradation in cell membranes, a process which can occur by two mechanisms: Type I (via free radicals) and Type II (mediated by 1O2). In the present work, several dyads have been synthesized from β- and α-Ch and ketoprofen (KP) or tiaprofenic acid (TPA). Upon irradiation under anaerobic conditions, KP–α-Ch dyads were efficiently photolyzed, via intramolecular hydrogen abstraction from C-7. By contrast, KP–β-Ch, TPA–α-Ch, and TPA–β-Ch remained unchanged after prolonged irradiation. The transient absorption spectra of KP–α-Ch were assigned to the short-lived biradicals resulting from intramolecular hydrogen abstraction. Interestingly, the spectra and lifetimes obtained for the TPA-derived dyads were very similar to those of the TPA triplet excited state. For the KP–α-Ch dyads, generation of singlet oxygen was expectedly negligible. Conversely, for TPA–α-Ch a ΦΔ value as high as 0.5 was determined. Thus, KP-based dyads are appropriate models for clean type I Ch oxidation, whereas the TPA derivatives are suitable systems for investigation of the purely type II process.

  胆固醇（Ch）是细胞膜中氧化降解的主要目标，这一过程可以通过两种机制发生：I型（通过自由基）和II型（通过1O2介导）。在本工作中，已从β-和α-Ch以及酮洛芬（KP）或噻洛芬酸（TPA）合成了几种二元组。在厌氧条件下照射下，KP-α-Ch二元组通过C-7的分子内氢提取高效光裂解。相比之下，KP-β-Ch、TPA-α-Ch和TPA-β-Ch在长时间照射后保持不变。KP-α-Ch的瞬态吸收光谱归因于由分子内氢提取产生的短寿命双自由基。有趣的是，从TPA衍生的二元组获得的光谱和寿命与TPA三重激发态非常相似。对于KP-α-Ch二元组，预计单线态氧的生成可以忽略不计。相反，对于TPA-α-Ch，测得的ΦΔ值高达0.5。因此，基于KP的二元组是清洁型I Ch氧化的适当模型，而TPA衍生物是研究纯型II过程的合适系统。
• Efficient and Selective Photogeneration of Cholesterol-Derived Radicals by Intramolecular Hydrogen Abstraction in Model Dyads
  作者：Inmaculada Andreu、Francisco Boscá、Laura Sanchez、Isabel M. Morera、Pelayo Camps、Miguel A. Miranda

  DOI：10.1021/ol061854c

  日期：2006.9.1

  [GRAPHICS]Three model dyads have been synthesized by esterification of beta- and alpha-cholesterol (Ch) with (S)- and/or (R)-ketoprofen (Kp). The alpha-dyads are efficient photogenerators of the 7-allyl Ch radicals by intramolecular H abstraction. Subsequent cyclization via C-C coupling occurs in a stereoselective way.
• Solvent Effects in Hydrogen Abstraction from Cholesterol by Benzophenone Triplet Excited State
  作者：Inmaculada Andreu、Fabrizio Palumbo、Fedele Tilocca、Isabel M. Morera、Francisco Boscá、Miguel A. Miranda

  DOI：10.1021/ol2016059

  日期：2011.8.5

  Hydrogen abstraction from the C-7 position of cholesterol (Ch) by triplet excited benzophenone (BZP) exhibits remarkable solvent-dependence in product studies. Kinetic measurements on the intramolecular version of the process in dyads containing covalently linked Ch and BZP units reveal important solvent effects and significant stereodifferentiation.

  在产物研究中，三重激发的二苯甲酮（BZP）从胆固醇（Ch）的C-7位置提取氢表现出显着的溶剂依赖性。在含有共价连接的Ch和BZP单元的二元组中，分子内版本过程的动力学测量显示出重要的溶剂作用和显着的立体分化。