(3S,8S,9S,10R,13R,14S,17S)-17-ethyl-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate | 3090-79-7

• 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: (3S,8S,9S,10R,13R,14S,17S)-17-ethyl-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate
• 英文别名: 3β-acetoxy-pregn-5-ene；3β-Acetoxy-pregn-5-en；Pregnen-(5)-yl-(3β)-acetat；Essigsaeure-(pregnen-(5)-yl-(3β)-ester)；(10R)-3c-Acetoxy-10r.13c-dimethyl-17c-aethyl-(8cH.9tH.14tH)-Δ⁵-tetradecahydro-1H-cyclopenta[a]phenanthren；[(3S,8S,9S,10R,13R,14S,17S)-17-ethyl-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 3090-79-7
• 化学式: C₂₃H₃₆O₂
• 分子量: 344.538
• InChiKey: WJWDCRHIOOHQLQ-ZGDAFCCHSA-N

物化性质

• 熔点：
  151-152 °C
• 沸点：
  422.2±24.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 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：

  (3S,8S,9S,10R,13R,14S,17S)-17-ethyl-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate 在 sodium dichromate 、 乙酸酐 、 溶剂黄146 作用下， 生成 7-oxopregn-5-en-3β-yl acetate
  参考文献：
  名称：

  Mailloux,M. et al., Bulletin de la Societe Chimique de France, 1970, p. 3627 - 3630

  摘要：

  DOI：
• 作为产物：
  描述：

  21-乙酰氧基孕烯醇酮 在 乙醇 、 sodium ethanolate 、 肼 作用下， 生成 (3S,8S,9S,10R,13R,14S,17S)-17-ethyl-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate
  参考文献：
  名称：

  516.分子旋转差异法在类固醇上的应用。第十一部分。Wolff–Kishner减少肾上腺皮质侧链

  摘要：

  DOI：

  10.1039/jr9490002456

文献信息

• Reaction of (20S)-3.BETA.-acetoxybisnorchol-5-enic acid with lead tetraacetate. Structure of pregnane derivatives and a dimer.
  作者：YOSHIHIRO SATO、YOSHIKO SONODA

  DOI：10.1248/cpb.30.822

  日期：——

  Reaction of 3β-acetoxybisnorchol-5-enic acid (1) with lead tetraacetate in benzene gave ⊿20 and ⊿17 (20) compounds (2a and 2b) and 20α-and 20β-acetoxy compounds (3a and 3b), with a trace of 20-keto compound (4) and a dimer (5). The structure of 5 was determined as 3'β-acetoxypregn-5'-en-20'α-yl 3β-acetoxybisnorchol-5-enate (Chart 1). The use of toluene or xylene in place of benzene resulted in decreased formation of 2b with the formation of the 17-ethyl compound (2c). The reactions were examined under various conditions (Table I) and the reaction mechanisms are discussed.

  3β-乙酰氧基双去氢胆甾-5-烯酸（1）与四乙酰铅在苯中反应生成了⊿20和⊿17（20）化合物（2a和2b）以及20α-和20β-乙酰氧基化合物（3a和3b），同时生成微量的20-酮化合物（4）和一个二聚体（5）。化合物5的结构被确定为3'β-乙酰氧基孕-5'-烯-20'α-基3β-乙酰氧基双去氢胆甾-5-烯酸酯（见图1）。用甲苯或二甲苯代替苯，导致2b的生成减少，同时生成了17-乙基化合物（2c）。在各种条件下对反应进行了研究（见表I），并讨论了反应机制。
• Steroids and sex hormones. Part 262. The radical induced stannane reduction of selenoesters and selenocarbonates: A new method for the degradation of carboxylic acids to nor-alkanes and for desoxygenation of alcohols to alkanes
  作者：Johannes Pfenninger、Christoph Heuberger、Walter Graf

  DOI：10.1002/hlca.19800630823

  日期：1980.12.10

  Esters of carboselenoic acids, formed from carboxylic acids by conventional methods, undergo reaction with tributyltin hydride in inert aromatic solvents, either by heating to give the corresponding aldehyde or the corresponding alkane depending on reaction temperature and the structure of the parent carboxylic acid, or by ultraviolet irradiation at ambient temperature when the aldehyde is formed predominantly

  通过常规方法，由羧酸形成的碳硒烯酸酯与三丁基锡氢化物在惰性芳族溶剂中反应，取决于反应温度和母体羧酸的结构，通过加热生成相应的醛或相应的烷烃，或通过当主要以高产率形成醛时，在环境温度下进行紫外线照射。在α，β-不饱和碳硒烯酸酯的情况下，热反应仅导致相应的醛。
• Ozonolysis of cholesterol and other Δ5-steroids in the presence of alcohols: a revised mechanism and hydroperoxide structure of the solvent-participated product, confirmed by X-ray analysis
  作者：Zdzisław Paryzek、Urszula Rychlewska

  DOI：10.1039/a702633a

  日期：——

  The structure of the product formed in the course of the reaction of cholesterol acetate and other Δ5-steroids with ozone in alcohol-containing solvents has been revised. The solvent-participated products are hydroperoxides, 5α-hydroperoxy-7α-alkoxy-5α-B-homo-6-oxasteroids 3 and not the previously claimed cyclic hemiperacetals, 5α-hydroxy-7a-alkoxy-B-dihomo-6,7-dioxacholestane derivatives 1. The final

  形成在胆甾醇乙酸酯的反应和其它Δ的过程中对产品的结构5在含醇的溶剂-steroids用臭氧已经修订。参与溶剂的产物是氢过氧化物，5α-氢过氧-7α-烷氧基-5α-B-homo-6-氧杂类固醇3而不是先前要求保护的环状半缩醛，5α-羟基-7a-烷氧基-B-dihomo-6,7-二氧杂胆甾烷衍生物1.从选定的氢过氧化物3a，3c和3j的X射线晶体结构分析中获得了最后的证据。提出涉及氢过氧基和烷氧基的氢键负责这些氢过氧化物的稳定性，并且在醇对Criegee中间体12的亲核进攻中也起指导作用。
• Electrochemical Deoxygenative Hydrogenation and Deuteration of Aldehydes/Ketones by Protic Acids in Water
  作者：Zhihui Sun、Ruixue Ji、Jintao Wu、Jianyou Zhao、Fang Fang、Fan Wang、Chao Jiang、Zhong‐Quan Liu

  DOI：10.1002/adsc.202201367

  日期：2023.2.21

  with aqueous H(D)Cl in an undivided cell, aliphatic and aromatic aldehydes and ketones undergo deoxygenative hydrogenation and deuterization to give hydrocarbons and deuterocarbons. The general features of this transformation are: 1) H+/D+ as the sources of H/D; 2) mild reaction conditions (room temperature, open flask, CH3CN and water as cosolvent); 3) easily scaled-up to 100 grams. A series of D-labeled

  我们在此报告修改后的 Clemmensen 还原。当在未分隔的电池中与 H(D)Cl 水溶液反应时，脂肪族和芳香族醛和酮会发生脱氧氢化和氘化反应，生成烃类和氘代烃。这种转化的一般特征是： 1）H + /D +作为H/D的来源；2)温和的反应条件(室温，开口烧瓶，CH 3 CN和水作为共溶剂)；3) 轻松放大至 100 克。通过该方法合成了一系列D标记的药物。
• Ouannes,C. et al., Bulletin de la Societe Chimique de France, 1964, p. 776 - 782
  作者：Ouannes,C. et al.

  DOI：——

  日期：——