5α-cholestan-3-one ethylene ketal | 1858-14-6

• 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-cholestan-3-one ethylene ketal
• 英文别名: (5α)-cholestan-3-one cyclic 1,2-ethanediyl acetal；cyclic-1,2-ethanediyl aetal cholestan-3-one；3,3-ethanediyldioxy-5α-cholestane；3,3-Aethandiyldioxy-5α-cholestan；(5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]spiro[1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,2'-1,3-dioxolane]
• CAS: 1858-14-6
• 化学式: C₂₉H₅₀O₂
• 分子量: 430.715
• InChiKey: NCAQEOULCQQMGY-JQLPBIJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5α-cholestan-3-one ethylene ketal 在 对甲苯磺酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.33h， 以94%的产率得到5-Alpha-胆甾烷-3-酮
  参考文献：
  名称：

  Regiocontrolled coupling of (.pi.-allylic)palladium complexes with organozirconium species

  摘要：

  DOI：

  10.1021/ja00369a028
• 作为产物：
  描述：

  3,3-ethane-1,2-diyldioxy-cholest-5-ene 在 Pd-BaSO₄ 、 乙醇 作用下， 生成 5α-cholestan-3-one ethylene ketal
  参考文献：
  名称：

  Preparation of Ethylenedioxy Derivatives of Ketosteroids by Exchange Dioxolanation. An Improved Synthesis of Testosterone from Δ⁴-Androstene-3,17-dione¹

  摘要：

  DOI：

  10.1021/ja01634a050

文献信息

• A New Ready, High-Yielding, General Procedure for Acetalization of Carbonyl Compounds
  作者：Romualdo Caputo、Carla Ferreri、Giovanni Palumbo

  DOI：10.1055/s-1987-27955

  日期：——

  Carbonyl compounds are smoothly and rapidly acetalized by treatment with alcohols, in anhydrous acetonitrile, in the presence of polystyryl diphenyl phosphine - iodine complex as catalyst. Open and cyclic acetals, including 1,3-dioxolanes, 1,3-oxathiolanes, and 1,3-dithiolanes, of miscellaneous aldehydes and ketones have been successfully prepared in this way. The isolation of the product is very easily performed, by simple filtration of the polymer-linked phosphine oxide which is formed in the reaction.

  通过使用醇类、无水乙腈中，在聚苯乙烯二苯基膦-碘复合物作为催化剂的条件下，羰基化合物可以顺利且快速地进行缩醛化反应。多种醛和酮的开链型和环状缩醛，包括1,3-二氧戊环、1,3-氧硫环戊烷和1,3-二硫环戊烷，都已成功通过这种方式制备。产品很容易通过简单过滤反应中形成的聚合物连接的磷氧化物来分离。
• Montmorillonite Clay Catalysis. Part 2.1 An Efficient and Convenient Procedure for the Preparation of Acetals catalysed by Montmorillonite K-10
  作者：Tong-Shuang Li、Sheng-Hui Li、Ji-Tai Li、Hui-Zhang Li

  DOI：10.1039/a605661j

  日期：——

  Acetalization of aldehydes and ketones is catalysed by montmorillonite K-10 in refluxing benzene or toluene in excellent yields.

  醛和酮的缩醛反应在沸腾的苯或甲苯中由膨润土 K-10 催化，产率极高。
• Selective Rhenium-Catalyzed Oxidation of Secondary Alcohols with Methyl Sulfoxide in the Presence of Ethylene Glycol, a Convenient One-Pot Synthesis of Ketals
  作者：Jeffrey B. Arterburn、Marc C. Perry

  DOI：10.1021/ol990755e

  日期：1999.9.1

  [reaction: see text] Secondary alcohols are oxidized preferentially by DMSO and the catalyst ReOCl3(PPh3)2 in the presence of ethylene glycol and refluxing toluene, producing the corresponding ketals. The reactions are rapid, and proceed in very good to excellent yields. The byproducts of the reaction, methyl sulfide and water, are easily removed. No epoxidation or other common side reactions were

  [反应：参见正文]在乙二醇和回流的甲苯存在下，DMSO和催化剂ReOCl3（PPh3）2优先将仲醇氧化，生成相应的缩酮。反应是快速的，并且以非常好的产率进行。反应的副产物甲基硫化物和水很容易除去。没有观察到环氧化或其他常见的副反应。醇向被保护的缩酮衍生物的这种直接氧化转化应具有广泛的合成适用性。
• BIS(DIISOBUTYLALUMINUM) 1,2-ETHANEDITHIOLATE: A REAGENT IN THE CONVERSION OF OXYACETALS TO THIOACETALS
  作者：TsuyoShi Satoh、Satoru Uwaya、Koji Yamakawa

  DOI：10.1246/cl.1983.667

  日期：1983.5.5

  Bis(diisobutylaluminum) 1,2-ethanedithiolate (9) made from diisobutylaluminum hydride and ethanedithiol in benzene is useful to convert oxyacetals into thioacetals, however not effective to ketones.

  双（二异丁基铝）1,2-乙二硫醇（9）由氢化二异丁基铝和乙二硫醇在苯中制成，可用于将氧乙酸酯转化为硫代乙酸酯，但对酮类无效。
• Rearrangement of steroidal epoxides and opening of steroidal ketals by alkyllithiums
  作者：Herbert L. Holland、Jahangir

  DOI：10.1016/s0040-4039(00)81714-1

  日期：——

  The ethylene ketal of 5,6α-epoxycholestan-3-one is converted to a ketalised Δ4-6α-ol on treatment with n-BuLi. However, the corresponding β epoxide undergoes opening of the ketal ring in the same reaction. Methyl- and n-butyl-lithium also react with the ethylene ketal of 3-ketocholestanes to give 3-alkyl cholestan-3-ols. The stereoselectivity of this reaction is discussed and a mechanism involving

  5,6α-epoxycholestan -3-酮的亚乙基缩酮被转化为ketalisedΔ 4 -6α醇上治疗用n-BuLi。然而，在相同反应中，相应的β-环氧化物经历了缩酮环的打开。甲基和正丁基锂也与3-酮胆甾醇的乙烯缩酮反应，生成3-烷基胆甾烷-3-醇。讨论了该反应的立体选择性，并提出了涉及1,2氢化物位移的机理。