5α,14β-cholestan-11-dione | 69483-53-0

• 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,14β-cholestan-11-dione
• 英文别名: 5α,14β-cholestane-11-one；5α,14β-Cholestan-11-on；(5R,8S,9S,10S,13R,14R,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,3,4,5,6,7,8,9,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-11-one
• CAS: 69483-53-0
• 化学式: C₂₇H₄₆O
• 分子量: 386.662
• InChiKey: UVQLQNWMLPIROZ-BYBPFRLTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5α,14β-cholestan-11-dione 在 吡啶 、 3,5-二甲基吡唑 、 chromium(VI) oxide 、 lithium aluminium tetrahydride 、 三氯氧磷 作用下， 以 乙醚 为溶剂， 生成 14β-Cholest-8-en-11-on
  参考文献：
  名称：

  Stereochemical course of the chemical and catalytic reduction of 11-oxo-5.alpha.,14.beta.-cholest-8-en-3.beta.-ol. Synthesis of 8.alpha.,9.alpha.,14.beta.-, 8.alpha.,9.beta.,14.beta.-, and 8.beta.,9.alpha.,14.beta.-steroids

  摘要：

  DOI：

  10.1021/jo01325a027
• 作为产物：
  描述：

  5α,14β-cholest-8-en-3β-ol-11-one 在 chromium(VI) oxide 、 氢氧化钾 、 硫酸 、 氨 、 lithium 、 一水合肼 、 二乙二醇 作用下， 生成 5α,14β-cholestan-11-dione
  参考文献：
  名称：

  Stereochemical course of the chemical and catalytic reduction of 11-oxo-5.alpha.,14.beta.-cholest-8-en-3.beta.-ol. Synthesis of 8.alpha.,9.alpha.,14.beta.-, 8.alpha.,9.beta.,14.beta.-, and 8.beta.,9.alpha.,14.beta.-steroids

  摘要：

  DOI：

  10.1021/jo01325a027

文献信息

• Mass spectrometry in structural and stereochemical problems. 2617—The effect of stereochemistry on the course of the characteristic ringD fragmentation of steroid hydrocarbons
  作者：Donald G. Patterson、M. J. Haley、I. Midgley、Carl Djerassi

  DOI：10.1002/oms.1210191102

  日期：1984.11

  AbstractThe ring D cleavage of the sterol skeleton with loss of carbon atoms 15, 16 and 17 together with the side‐chain is one of the most characteristic and structurally useful mass spectral features of steroids. It has been tacitly assumed that the hydrogen rearrangements accompanying this process are not sensitive to stereochemical changes. Using deuterium labeling it has now been demonstrated that the stereochemistry at various positions of the nucleus, notably 8, 9 and 14, strongly affects this process. Possible rationalizations for this unexpected observation are presented.
• Stereochemical course of the chemical and catalytic reduction of 11-oxo-5.alpha.,14.beta.-cholest-8-en-3.beta.-ol. Synthesis of 8.alpha.,9.alpha.,14.beta.-, 8.alpha.,9.beta.,14.beta.-, and 8.beta.,9.alpha.,14.beta.-steroids
  作者：Donald G. Patterson、Carl Djerassi

  DOI：10.1021/jo01325a027

  日期：1979.5