(3beta,5alpha)-胆甾-8(14)-烯-3-基乙酸酯 | 6562-21-6

• 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
• 中文名称: (3beta,5alpha)-胆甾-8(14)-烯-3-基乙酸酯
• 英文名称: 3β-(Acetyloxy)-5α-cholest-8(14)-ene
• 英文别名: 5α-cholest-8(14)-en-3β-ol acetate；3β-acetoxy-5α-cholest-8(14)-ene；3β-Acetoxy-5α-cholest-8(14)-en；(10S)-3c-Acetoxy-10r.13c-dimethyl-17c-((R)-1.5-dimethyl-hexyl)-(5tH.9tH)-Δ⁸⁽¹⁴⁾-tetradecahydro-1H-cyclopenta[a]phenanthren；Essigsaeure-[5α-cholesten-(8(14))-yl-(3β)-ester]；5α-Cholesten-(8(14))-yl-(3β)-acetat；5alpha(H),17alpha(H)-(20R)-3beta-ACETOXYCHOLEST-8(14)-ENE；[(3S,5S,9R,10S,13R,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 6562-21-6
• 化学式: C₂₉H₄₈O₂
• 分子量: 428.699
• InChiKey: VNJBUCCXHRSVLO-ZSKZXBCESA-N

物化性质

• 熔点：
  73-74 °C
• 沸点：
  493.8±44.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 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：

  (3beta,5alpha)-胆甾-8(14)-烯-3-基乙酸酯 在 chromium(VI) oxide 、 溶剂黄146 、 苯 作用下， 生成 3β-acetoxy-8α,14α-epoxy-5α-cholestan-7-one
  参考文献：
  名称：

  The Dehydration of the 7-Epimeric 3(β)-Acetoxycholestanols-7. Some Transformation Products of γ-Cholestenol

  摘要：

  DOI：

  10.1021/ja01248a022
• 作为产物：
  描述：

  cholesterol 在 吡啶 、 丙醇 、 乙醇 、 sodium 作用下， 生成 (3beta,5alpha)-胆甾-8(14)-烯-3-基乙酸酯
  参考文献：
  名称：

  ?-Cholestenon und epi-?-Cholestenon

  摘要：

  DOI：

  10.1002/hlca.19470300532

文献信息

• Structure – chiroptical properties relationship of cisoid enones with an α-methylenecyclopentanone unit
  作者：Jadwiga Frelek、Aleksandra Butkiewicz、Marcin Górecki、Ryszard K. Wojcieszczyk、Roman Luboradzki、Marcin Kwit、Michał F. Rode、Wojciech J. Szczepek

  DOI：10.1039/c4ra04991h

  日期：——

  In the present work, the validity of sector and helicity rules correlating the stereostructure of cis-enones containing the 2-methylenecyclopentanone unit with the sign of the nπ* Cotton effect (CE) observed in their electronic circular dichroism (ECD) spectra is assessed. To this end, a series of model steroid cis-enones with five-membered ketone rings was synthesized. To investigate the scope and limitations of existing rules a combination of ECD spectroscopy, X-ray analysis, and time-dependent density functional theory (TD-DFT) calculations were utilized. A comparison of the experimental ECD spectra with spectra simulated by the TD-DFT calculations gave a reasonable interpretation of the nπ* CE's observed in the 360–335 nm spectral range. The results suggest that the previously articulated rules are not applicable to the investigated compounds. On the basis of comprehensive analysis of collected data, a new rule correlating perfectly the structure of studied enones with the signs of their nπ* CE was proposed. This rule correlates directly the sign of the torsion angle “b” of the cyclopentanone ring of cis-enone with the sign of the nπ* CE.

  在本研究工作中，评估了与含有2-亚甲基环戊酮单元的顺式环烯酮的立体结构相关的扇区和螺旋规则的有效性，这些规则关联了它们在电子圆二色性(ECD)光谱中观察到的n→π* Cotton效应(CE)的符号。为此，合成了一系列具有五元酮环的模型甾体顺式环烯酮。为了探究现有规则的适用范围和局限性，采用了ECD光谱学、X射线分析和含时密度泛函理论(TD-DFT)计算相结合的方法。通过比较实验ECD光谱与由TD-DFT计算模拟的光谱，对在360-335 nm光谱范围内观察到的n→π* CE给出了合理的解释。结果表明，先前阐述的规则不适用于所研究的化合物。基于对收集数据的全面分析，提出了一条与所研究环烯酮结构完美关联的新规则，该规则直接关联顺式环烯酮的环戊酮环的扭转角“b”的符号与n→π* CE的符号。
• Inhibitors of sterol synthesis. Synthesis and spectral properties of 3β-hydroxy-5α-cholestan-15-one and its 14β-epimer and their effects on 3-hydroxy-3-methylglutaryl coenzyme A reductase activity
  作者：Abdul U. Siddiqui、William K. Wilson、Edward J. Parish、Nicolas Gerst、Frederick D. Pinkerton、George J. Schroepfer

  DOI：10.1016/0009-3084(94)90106-6

  日期：1994.10

  resonance (NMR) spectra; chromatographic methods gave less reliable estimates of purity. NMR data also showed that ring C of the 14 beta sterols is predominantly in a chair conformation. The effects of 2a and 2b on the levels of 3-hydroxy-3-methylglutaryl coenzyme A reductase have been studied in Chinese hamster ovary cells.

  由3个β-乙酰氧基-5α-胆甾醇8（14）-烯（3）制备3个β-羟基-5α-胆甾醇-15-（2a）及其14个β-顶基2b。3在45-50℃下进行硼氢化，得到5α，14α-胆甾烷3β，15α-二醇和5α，14β-胆甾烷3β，15β-二醇的混合物，将其在硅胶上分离凝胶作为它们的3个β-叔丁基二甲基甲硅烷基醚5a和5b。用氯铬酸吡啶鎓氧化5a，然后用氟化四丁基铵进行甲硅烷基化，得到2a。5b的类似转化产生被2a污染的2b。5b的甲硅烷基化反应，然后用氯铬酸吡啶鎓氧化，得到的混合物主要由5α，14β-胆甾烷-3,15-二酮和2b组成。在硅胶和反相介质上的连续色谱分离得到2b高纯度。还通过锂氨还原3个β-羟基-5α-胆甾8（14）-en-15-one（96％收率）和选择性还原5个α-胆甾烷3,15-制备化合物2a二酮与三叔丁氧基氢化铝锂（产率90％）。异构体2a和2b易于在酸性或碱性条件下或在气相色
• Oxygenated sterol derivatives. Their identification from the fungus-infected silkworm carcass, Bombyx cum Botryte, and their effects on growth and sterol metabolism of the silkworm, Bombyx mori.
  作者：BAIPING YING、MASUO MORISAKI、NOBUO IKEKAWA

  DOI：10.1248/cpb.32.3003

  日期：——

  Several oxygenated sterols, e.g. ergosterol peroxide, 7-oxocholesterol and 7β-hydroxycholesterol, were identified from the fungus-infected carcass of silkworm, Bombyx cum Botryte. However, they were nontoxic to the silkworm Bombyx mori reared on a diet containing these oxygenated sterols (0.01%) together with sitosterol or cholesterol (0.1%).

  从受真菌感染的蚕尸体中识别出几种含氧甾醇，例如麦角甾醇过氧化物、7-氧胆固醇和7β-羟胆固醇。然而，它们对以含有这些氧化甾醇（0.01%）以及植物甾醇或胆固醇（0.1%）为饲料的家蚕（Bombyx mori）无毒性。
• Zur Dehydrobromierung von 7-Brom-cholesteryl-benzoat: Abnorme Produkte
  作者：F. Hunziker、F. X. Müllner、K. G. Reuteler、H. Schaltegger

  DOI：10.1002/hlca.19550380535

  日期：——

  Verschiedene Beobachtungen bei der Dehydrobromierung von 7-Brom-cholesterylbenzoat werden mitgeteilt.

  报道了关于7-溴-胆固醇基苯甲酸酯的脱氢溴化的各种观察结果。
• 275. Studies in the sterol group. Part XLII. The constitution of zymosterol
  作者：B. Heath-Brown、I. M. Heilbron、E. R. H. Jones

  DOI：10.1039/jr9400001482

  日期：——