cholest-4-en-3-one | 38777-61-6

• 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: cholest-4-en-3-one
• 英文别名: (8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2S)-6-methylheptan-2-yl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS: 38777-61-6
• 化学式: C₂₇H₄₄O
• 分子量: 384.646
• InChiKey: NYOXRYYXRWJDKP-QAKPMDPSSA-N

物化性质

• 沸点：
  482.7±12.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  cholest-4-en-3-one 、 三氯乙酸酐 生成 3-Trichloracetoxy-Δ^3,5-cholestadien
  参考文献：
  名称：

  酸酐-IV的反应：甾类3-三氯乙酸基-Δ 3,5 -dienes; Δ的一个简单的去缀合4 -3-酮

  摘要：

  甾体Δ 4 -3-酮1，4和5，由此导致3-三氯乙酸基-Δ三氯乙酸酐反应3,5- -dienes 2，6和7。光谱或其它微碱性甲醇转换3-三氯乙酸基二烯2和7为相应的Δ 5 -3-酮3和8。其甲醇分解的速率比所得到的Δ的异构化反应的快得多5 -3-酮3和8为更稳定的Δ 4-酮1和5。该3-乙酰氧基二烯的甲醇分解16还可以导致初级形成Δ的5 -3-酮3C，但由于其形成的速率是比得上其异构化到Δ的4 -3-酮，该前一种化合物不可分离。该Δ 4,6 -3-酮10和14也得到3-三氯乙酸基-Δ 3,5,7 -三烯11和15，前者在甲醇分解，得到的Δ的混合物5,7- -3-酮12，和该Δ 3,7 -3-酮13。

  DOI：

  10.1016/s0040-4020(01)82744-7
• 作为产物：
  描述：

  3β-hydroxy-5α, 6β-dibromocholestane 在 Jones reagent 、 草酸 、 溶剂黄146 、 锌 作用下， 以 乙醚 、 丙酮 为溶剂， 生成 cholest-4-en-3-one
  参考文献：
  名称：

  Structural elucidation, density functional calculations and contribution of intermolecular interactions in cholest-4-en-3-one crystals: Insights from X-ray and Hirshfeld surface analysis

  摘要：

  The foremost objective of the present work is systematic analysis of intermolecular interactions in crystal structure of cholest-4-en-3-one (2) molecule. It is accomplished by Hirshfeld surface analysis and fingerprint plot. Hirshfeld surface analysis has been used to visualize the fidelity of the crystal structure. This method permitted for the identification of individual types of intermolecular contacts and their impact on the complete packing. Molecules are linked by a combination of C=O-H, C-H-H, and C-H contacts, which have clear signatures in the fingerprint plots. The theoretical study was attempted to predict the optimized geometry and computed spectra by the Density Functional Theory (DFT) using the B3LYP function with the 6-311++G(d,p) basis set. Atomic charges, MEP mapping, HOMO-LUMO, various thermodynamic and molecular properties have been reported. In addition thermal stability, optical, morphological, and microstructral properties of the title compound (2) have also been explored. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2014.12.027

文献信息

• Reaction of acid anhydrides—IV
  作者：D. Amar、V. Permutti、Y. Mazur

  DOI：10.1016/s0040-4020(01)82744-7

  日期：1969.1

  Steroidal Δ4-3-ketones 1, 4 and 5 react with trichloroacetic anhydride resulting in 3-trichloroacetoxy-Δ3,5-dienes 2, 6 and 7. Spectroscopic or other slightly basic methanol converts the 3-trichloroacetoxy-dienes 2 and 7 into the corresponding Δ5-3-ketones 3 and 8. The rate of its methanolysis is much faster than that of the isomerization reaction of the resulting Δ5-3-ketones 3 and 8 to the more stable

  甾体Δ 4 -3-酮1，4和5，由此导致3-三氯乙酸基-Δ三氯乙酸酐反应3,5- -dienes 2，6和7。光谱或其它微碱性甲醇转换3-三氯乙酸基二烯2和7为相应的Δ 5 -3-酮3和8。其甲醇分解的速率比所得到的Δ的异构化反应的快得多5 -3-酮3和8为更稳定的Δ 4-酮1和5。该3-乙酰氧基二烯的甲醇分解16还可以导致初级形成Δ的5 -3-酮3C，但由于其形成的速率是比得上其异构化到Δ的4 -3-酮，该前一种化合物不可分离。该Δ 4,6 -3-酮10和14也得到3-三氯乙酸基-Δ 3,5,7 -三烯11和15，前者在甲醇分解，得到的Δ的混合物5,7- -3-酮12，和该Δ 3,7 -3-酮13。
• Structural elucidation, density functional calculations and contribution of intermolecular interactions in cholest-4-en-3-one crystals: Insights from X-ray and Hirshfeld surface analysis
  作者：Hena Khanam、Ashraf Mashrai、Nazish Siddiqui、Musheer Ahmad、Mohammad Jane Alam、Shabbir Ahmad、Shamsuzzaman

  DOI：10.1016/j.molstruc.2014.12.027

  日期：2015.3

  The foremost objective of the present work is systematic analysis of intermolecular interactions in crystal structure of cholest-4-en-3-one (2) molecule. It is accomplished by Hirshfeld surface analysis and fingerprint plot. Hirshfeld surface analysis has been used to visualize the fidelity of the crystal structure. This method permitted for the identification of individual types of intermolecular contacts and their impact on the complete packing. Molecules are linked by a combination of C=O-H, C-H-H, and C-H contacts, which have clear signatures in the fingerprint plots. The theoretical study was attempted to predict the optimized geometry and computed spectra by the Density Functional Theory (DFT) using the B3LYP function with the 6-311++G(d,p) basis set. Atomic charges, MEP mapping, HOMO-LUMO, various thermodynamic and molecular properties have been reported. In addition thermal stability, optical, morphological, and microstructral properties of the title compound (2) have also been explored. (C) 2014 Elsevier B.V. All rights reserved.