5α-cholestane-3,7-dione | 13400-67-4

• 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-cholestane-3,7-dione
• 英文别名: 5alpha-Cholestane-3,7-dione；(5R,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,4,5,6,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,7-dione
• CAS: 13400-67-4
• 化学式: C₂₇H₄₄O₂
• 分子量: 400.645
• InChiKey: GLGKHJIHOAQVPU-JCNPAGMSSA-N

物化性质

• 熔点：
  178-179 °C
• 沸点：
  499.2±28.0 °C(Predicted)
• 密度：
  0.996±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5α-cholestane-3,7-dione 在 sodium triethoxyborohydride 、 sodium cyanoborohydride 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 20.0h， 生成 3alpha,7alpha-Bis[2-(5-imidazolyl)ethyl]amino-5alpha-cholestane
  参考文献：
  名称：

  Synthesis and antimicrobial activity of imidazole and pyridine appended cholestane-based conjugates

  摘要：

  A series of 3 alpha-amino-5 alpha-cholestane and 3 alpha,7 alpha-diamino-5 alpha-cholestane derivatives containing imidazole and pyridine rings were synthesized by simple and effective reductive amination, and their in vitro activities against a range of Gram-positive and Gram-negative strains were evaluated. Most of the compound exhibited enhanced activity against MRSA pathogen. 3 alpha,7 alpha-Di(pyridylmethyl)amino-5 alpha-cholestane 10 showed the highest potency in these series toward the Gram-positive bacteria, Staphylococcus epidermidis 887E, with the lowest MIC value of 1 mu g/mL. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.05.098
• 作为产物：
  描述：

  5α-cholestane-3β,7β-diol 在 chromium(VI) oxide 、 溶剂黄146 作用下， 生成 5α-cholestane-3,7-dione
  参考文献：
  名称：

  Sterols. LXXV. Cholesterol Derivatives

  摘要：

  DOI：

  10.1021/ja01266a011

文献信息

• Bile acids LXIX. Selective K-Selectride reduction of 3,7-diketo steroids
  作者：Daniel M. Tal、G. Douglas Frisch、William H. Elliott

  DOI：10.1016/s0040-4020(01)91473-5

  日期：1984.1

  The K-Selectride reduction at low temperature (-45°C) of 7-oxo-5α-holestan-3β-yl acetate and methyl 7-oxo-3α-hydroxy-5(β-cholanoate resulted in almost quantitative yield of the 7α-alcohol in the 5α-compound but only moderate yield of the 5β-analog. The simultaneous reduction of two carbonyl groups in the 3 and 7 positions afforded good to excellent yields of the diaxial diol in planar steroids (methyl

  7-氧代-5α-holestan-3β-乙酸乙烯酯和7-氧代-3α-羟基-5（β-胆酸甲酯）在低温（-45°C）下的K-Selectride还原导致几乎定量的7α收率-醇在5α-化合物中生成，但只有中等程度的5β-类似物生成。同时还原3和7位上的两个羰基可以使平面类固醇（3,7-二氧-甲基- 5α-胆酸酯，3,7-二氧代-5α-胆甾烷和3,7-二氧代-5α-胆甾烷-27-甲基丙烯酸酯）和14％的3α，7α-（OH）2来自3,7-二氧甲基- 5β-胆酸盐。
• The synthesis of facial amphiphile 3α,7α-diaminocholestane
  作者：Sharaf Nawaz Khan、Nam-Ju Cho、Hong-Seok Kim

  DOI：10.1016/j.tetlet.2007.05.157

  日期：2007.7

  The facial amphiphile 3α,7α-diaminocholestane 3 was synthesized from 3β-acetoxy-7-ketocholestane 1 through a stepwise reductive amination. The reductive amination of 1 with NH4OAc in the presence of NaBH3CN, and protection with Boc2O yielded 7α-(tert-butyloxycarbonyl)-aminocholestane 4 in 86% yield. The reductive amination of 6, which was obtained from 4 after hydrolysis and subsequent oxidation, with

  通过逐步还原胺化反应，由3β-乙酰氧基-7-酮胆甾烷1合成面部两亲物3α，7α-二氨基胆甾烷3。在NaBH 3 CN存在下用NH 4 OAc还原胺化1，并用Boc 2 O保护得到7α- （叔丁氧羰基）-氨基胆甾烷4，产率为86％。在NaBH（OEh）3存在下，用NH 4 OT f在水解和随后的氧化后从4获得的6的还原胺化反应提供了3用Boc 2 O保护后，产率为75％。
• Synthesis and antifungal activity of oxygenated cholesterol derivatives
  作者：J BRUNEL、C LONCLE、N VIDAL、M DHERBOMEZ、Y LETOURNEUX

  DOI：10.1016/j.steroids.2005.06.007

  日期：2005.12.1

  A series of oxygenated cholesterol derivatives were prepared from new synthetic methods and evaluated for their in vitro antimicrobial properties against human pathogens. The activity was highly dependent on the structure of the different compounds involved. The best results were obtained with hydroxy ketones 2, 4 and 5 and diketone 7 exhibiting activities against S. cerevisiae (ATCC 28383) and Candida albicans (CIP 1663-86). For example, compound 2 exhibited high activities against C. albicans (CIP 1663-86) and Amphotericine B and miconazole resistant strain C. albicans (CIP 1180-79) at a concentration of 1.5 mu g/mL. (c) 2005 Elsevier Inc. All rights reserved.
• The Hydration of Unsaturated Steroids by the Brown Hydroboration Reaction. I. Monounsaturated Steroids
  作者：Manasse Nussim、Yehuda Mazur、Franz Sondheimer

  DOI：10.1021/jo01028a032

  日期：1964.5
• 158. The application of the method of molecular rotation differences to steroids. Part IV. Optical anomalies
  作者：D. H. R. Barton、J. D. Cox

  DOI：10.1039/jr9480000783

  日期：——