5α-cholest-2-en-3-ol 3-acetate | 1255-89-6

• 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-cholest-2-en-3-ol 3-acetate
• 英文别名: 5α-cholest-2-en-3-ol acetate；acetoxy-3 (5α) cholestene-2；3-acetoxy-5α-cholest-2-ene；3-Acetoxy-5α-cholest-2-en；Cholest-2-en-3-ol-acetat；3-Acetoxy-cholesten-(2)；5alpha-Cholest-2-en-3-ol 3-acetate；[(5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 1255-89-6
• 化学式: C₂₉H₄₈O₂
• 分子量: 428.699
• InChiKey: YXUGUUGNHVVXAI-LIFKPSPXSA-N

物化性质

• 熔点：
  142-143 °C(Solv: ethanol (64-17-5))
• 沸点：
  504.9±17.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  31
• 可旋转键数：
  7
• 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-cholest-2-en-3-ol 3-acetate 在 甲基环氧丙烷 、 叔丁胺 作用下， 以 丙酮 为溶剂， 反应 72.0h， 生成 2α-acetoxy-5α-cholestan-3-one
  参考文献：
  名称：

  Synthesis and Biological Activity Of Unsymmetrical Bis-Steroidal Pyrazines Related to the Cytotoxic Marine Natural Product Cephalostatin 1

  摘要：

  A mild, high-yielding synthesis of symmetrical steroidal pyrazines was achieved from the dimerization of 2-amino-3-ketosteroids, which were produced in situ from the triphenylphosphine-water reduction of the corresponding alpha-azido ketone. 2-Azidocholestan-3-one gave the dimeric steroidal pyrazine very cleanly, and two known dimeric pyrazines based on androstanone were also made using this methodology. Both C-2-symmetric geometric isomers of the dimeric steroidal pyrazine derived from cholestane were prepared by reaction of 2,3-diaminocholestane with cholestane-2,3-dione. A route to unsymmetrical bis-steroidal pyrazines was based on the observation that alpha-acetoxy ketones react with alpha-amino oximes directly with no need for oxidation of intermediate dihydropyrazines. Heating either 2 beta,17 beta-dihydroxyandrostan-3-one diacetate or 2 beta,17 beta-dihydroxyhecogenin-3-one diacetate with 2-amino-3-methoxyiminocholestane in toluene at 145 degrees C gave the corresponding unsymmetrical pyrazine in moderate yield. Five of the steroidal pyrazines were evaluated in the National Cancer Institute's new in vitro, disease-oriented antitumor screen, but none showed sufficient activity to warrant in vivo investigation.

  DOI：

  10.1021/jo00101a052
• 作为产物：
  描述：

  5-Alpha-胆甾烷-3-酮 、 乙酸酐 在 montmorillonite clay 作用下， 以90%的产率得到5α-cholest-2-en-3-ol 3-acetate
  参考文献：
  名称：

  2,3-官能化的胆甾烷和雄烷酮衍生物的新颖，有效的合成和抗真菌评价

  摘要：

  胆固醇和其他传统类固醇分子的合成修饰已成为探索和开发新型抗真菌剂的有前途的领域，尤其是在类固醇脂肪酸酯的开发方面。另外，2，3-官能化的类固醇也是具有潜在令人感兴趣的生物学性质的化合物，并且2，3-类固醇的适当官能化可以导致开发有效合成的类固醇的脂肪酸酯的结构单元。在这封信中，我们概述了合成2，3-官能化的胆甾烷和雄烷酮衍生物的新颖而有效的方法，并提出了它们对许多真菌物种的有希望的初步抗真菌活性。

  DOI：

  10.1016/j.bmcl.2010.10.044

文献信息

• A method for the transformation of cyclic ketones to homologous α,β-unsaturated ketones
  作者：G. Stork、M. Nussim、B. August

  DOI：10.1016/s0040-4020(01)82174-8

  日期：1966.1

  The addition of dichlorocarbene to enol acetates of cyclic ketones can be carried out efficiently in many cases using the neutral trihalomethyl phenyl mercury reagents. Since enol acetates of definite structures are readily prepared, the method provides a convenient first step to a ring enlargement sequence which can be carried out under basic conditions.

  在许多情况下，使用中性三卤代甲基苯基汞试剂可以有效地将二氯卡宾添加到环状酮的烯醇乙酸酯中。由于容易制备具有确定结构的烯醇乙酸酯，因此该方法为环扩大序列提供了方便的第一步，该步骤可以在碱性条件下进行。
• Stéréochimie-LVII
  作者：Alain Calvet、Marcel Jozefowicz、Jacques Levisalles

  DOI：10.1016/s0040-4020(01)97635-5

  日期：——

  Absolute rates of bromination were measured for two series of derivatives of steroidal ketones 3, enol acetates 1 and enol methyl ether 2. Axial substituents exhibited a large effect on rates, which increased by 15,000 fold on going from (X=CH3; Y=CN) to (X=Y=H). From the bromide ion effect it was concluded that the first step (formation of an intermediate bromonium ion) was reversible and that the

  测量了甾族酮3的两个系列衍生物，烯醇乙酸酯1和烯醇甲基醚2的溴化绝对速率。轴向取代基对速率表现出很大的影响，从（X = CH 3； Y = CN）变为（X = Y = H）时，轴向取代基增加了15,000倍。从溴离子效应可以得出结论，第一步（中间体溴离子的形成）是可逆的，并且第二步（卤代酮4或5或卤代缩醛8或9的形成）与第一步相比较慢。推断该中间体是高度不对称的溴离子，而不是纯的氧碳鎓离子。
• Novel α-Iodination of Ketones Using Iodine/Copper(II) Acetate
  作者：Charles A. Horiuchi、James Y. Satoh

  DOI：10.1055/s-1981-29432

  日期：——
• Ali, S. Mahmoud; Clarke, David; Cliff, Geoffrey R., Journal of Chemical Research, Miniprint, 1981, # 8, p. 2901 - 2927
  作者：Ali, S. Mahmoud、Clarke, David、Cliff, Geoffrey R.、Morrison, George A.

  DOI：——

  日期：——
• The Reduction of Steroidal Enol Acetates with Lithium Aluminum Hydride and Sodium Borohydride
  作者：William G. Dauben、Robert A. Micheli、Jerome F. Eastham

  DOI：10.1021/ja01135a040

  日期：1952.8