cholest-5-en-3β-oxy-5-bromopentane | 335196-16-2

• 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-5-en-3β-oxy-5-bromopentane
• 英文别名: (3S,8S,9S,10R,13R,14S,17R)-3-(5-bromopentoxy)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene
• CAS: 335196-16-2
• 化学式: C₃₂H₅₅BrO
• 分子量: 535.692
• InChiKey: HOXPBPSODWHTAJ-RWFZIKKDSA-N

物化性质

• 沸点：
  561.6±43.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.9
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-dodecyloxy-4'-hydroxybiphenyl 、 cholest-5-en-3β-oxy-5-bromopentane 在 potassium carbonate 作用下， 以 丁酮 为溶剂， 生成 (3S,8S,9S,10R,13R,14S,17R)-3-[5-[4-(4-dodecoxyphenyl)phenoxy]pentoxy]-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene
  参考文献：
  名称：

  Smectic C Phases and Reentrant Behavior in Cholesterol Containing Dimer Liquid Crystals

  摘要：

  A series of dodecyloxybiphenylyl and cholesteryl group containing dimers with ethers as spacers have been prepared and their liquid crystalline properties were investigated as a function of spacer length. For short spacers SmA and SmC phases were observed with monolayer ordering. This is aparent from. polarization microscopy and temperature dependent X-ray measurements. With increasing spacer length a N*-phase gradually appears whose liquid crystalline range increases. For the dodecyl spacer no smectic phase is observed anymore. For the nonyl spacer reentrant behavior is found (N*-TGB-SmA-TGB-N*). Reentrant behavior, probably N*-TGB-N*, is also observed for a related compound with an ester spacer.

  DOI：

  10.1080/15421400490435035
• 作为产物：
  描述：

  1-(cholest-5-en-3β-yloxy)pentan-5-ol 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以97%的产率得到cholest-5-en-3β-oxy-5-bromopentane
  参考文献：
  名称：

  Structure of cholest-5-en-3β-oxy-5-bromopentane by single-crystal X-ray diffraction at 130 K

  摘要：

  Cholest-5-en-3 beta -oxy-5-bromopentane (1) and cholest-5-en-3 beta -oxy-11-bromoundecane (2), key precursors for the synthesis of novel cationic amphiphiles based on cholesterol, have been synthesized and characterized by H-1-NMR spectroscopy and X-ray crystallography. Thermal disorder and effect of length of the bromoalkyl segment on the crystal structure have been investigated. Possible molecular level explanation of the unusual alternating s-trans-gauche conformation of the bromopentyl side chain of (Ij has been presented. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-2860(00)00823-1

文献信息

• A Fluorescence Polarization Activity-Based Protein Profiling Assay in the Discovery of Potent, Selective Inhibitors for Human Nonlysosomal Glucosylceramidase
  作者：Daniël Lahav、Bing Liu、Richard J. B. H. N. van den Berg、Adrianus M. C. H. van den Nieuwendijk、Tom Wennekes、Amar T. Ghisaidoobe、Imogen Breen、Maria J. Ferraz、Chi-Lin Kuo、Liang Wu、Paul P. Geurink、Huib Ovaa、Gijsbert A. van der Marel、Mario van der Stelt、Rolf G. Boot、Gideon J. Davies、Johannes M. F. G. Aerts、Herman S. Overkleeft

  DOI：10.1021/jacs.7b07352

  日期：2017.10.11

  assessed on GBA2 selectivity offset against the other glucosylceramide metabolizing enzymes, glucosylceramide synthase (GCS), lysosomal glucosylceramidase (GBA), and the cytosolic retaining β-glucosidase, GBA3. Our work, yielding potent and selective GBA2 inhibitors, also provides a roadmap for the development of high-throughput assays for identifying retaining glycosidase inhibitors by FluoPol-ABPP

  人非溶酶体葡萄糖基神经酰胺酶（GBA2）是控制糖脂水平的几种酶之一，其活性与几种人类疾病状态相关。迫切需要设计或发现选择性的GBA2抑制剂作为化学工具和潜在的治疗剂。在这里，我们描述了基于荧光偏振活性的蛋白质谱分析（FluoPol-ABPP）测定法的发展，该测定法可从350多种亚氨基糖文库中快速鉴定GBA2抑制剂。基于FluoPol-ABPP筛选的线索生成聚焦库，并针对与其他葡糖神经酰胺代谢酶，葡糖神经酰胺合酶（GCS），溶酶体葡糖神经酰胺酶（GBA）和胞质保留β-葡糖苷酶GBA3的GBA2选择性偏移进行评估。我们的工作产生了有效的和选择性的GBA2抑制剂，
• Structure of cholest-5-en-3β-oxy-5-bromopentane by single-crystal X-ray diffraction at 130 K
  作者：Yamuna Krishnan-Ghosh、R. Srinivasa Gopalan、G.U. Kulkarni、Santanu Bhattacharya

  DOI：10.1016/s0022-2860(00)00823-1

  日期：2001.1

  Cholest-5-en-3 beta -oxy-5-bromopentane (1) and cholest-5-en-3 beta -oxy-11-bromoundecane (2), key precursors for the synthesis of novel cationic amphiphiles based on cholesterol, have been synthesized and characterized by H-1-NMR spectroscopy and X-ray crystallography. Thermal disorder and effect of length of the bromoalkyl segment on the crystal structure have been investigated. Possible molecular level explanation of the unusual alternating s-trans-gauche conformation of the bromopentyl side chain of (Ij has been presented. (C) 2001 Elsevier Science B.V. All rights reserved.
• Smectic C Phases and Reentrant Behavior in Cholesterol Containing Dimer Liquid Crystals
  作者：Antonius Marcelis、Arie Koudijs、Ernst Sudhölter

  DOI：10.1080/15421400490435035

  日期：2004.1

  A series of dodecyloxybiphenylyl and cholesteryl group containing dimers with ethers as spacers have been prepared and their liquid crystalline properties were investigated as a function of spacer length. For short spacers SmA and SmC phases were observed with monolayer ordering. This is aparent from. polarization microscopy and temperature dependent X-ray measurements. With increasing spacer length a N*-phase gradually appears whose liquid crystalline range increases. For the dodecyl spacer no smectic phase is observed anymore. For the nonyl spacer reentrant behavior is found (N*-TGB-SmA-TGB-N*). Reentrant behavior, probably N*-TGB-N*, is also observed for a related compound with an ester spacer.