3-cycloethylenedioxy-17β-O-(tetrahydropyranyl)-androst-5-ene | 55393-63-0

• 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: 3-cycloethylenedioxy-17β-O-(tetrahydropyranyl)-androst-5-ene
• 英文别名: 3,3-ethylenedioxy-17β-tetrahydropyranyloxy-5-androstene
• CAS: 55393-63-0
• 化学式: C₂₆H₄₀O₄
• 分子量: 416.601
• InChiKey: URNOMECFPAKJKD-BJZAAASJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  30.0
• 可旋转键数：
  2.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-cycloethylenedioxy-17β-O-(tetrahydropyranyl)-androst-5-ene 在 sodium hydroxide 、 硼烷 、 双氧水 作用下， 生成 3,3-ethylenedioxy-17β-tetrahydropyranyloxy-5α-androstan-6α-ol 、 3,3-ethylenedioxy-17β-tetrahydropyranyloxy-5β-androstan-6β-ol
  参考文献：
  名称：

  Synthesis of C-6 fluoroandrogens: Evaluation of ligands for tumor receptor imaging

  摘要：

  Seven androgens, substituted with fluorine at C-6, were prepared as potential imaging agents for androgen receptor-positive prostate tumors and were evaluated in vitro in terms of their lipophilicity and their relative binding affinities (RBA, relative to R 1881 = 100) for the androgen receptor and for sex steroid binding protein. Introduction of a fluorine atom into the C-6 position of an androgen generally decreases binding affinity to the androgen receptor, except in the two cases: 6 alpha-fluoro-19-nor-testosterone (RBA = 41.6 versus 30.6 for the unsubstituted steroid) and 6 alpha-fluoro-19-nor-testosterone (RBA = 8.9 versus 6.6). Receptor binding of the C-6 fluoro-androgens is also stereospecific, showing higher binding affinities for the alpha-epimers compared to the corresponding beta-epimers (4:1-15:1). Binding affinity to sex steroid binding protein is the lowest with 19-nor-testosterone, which is also the least lipophilic androgen studied. Based on the binding properties of compounds in this series, 6 alpha-fluoro-19-nor-testosterone appears to have the most promise as a turner imaging agent.

  DOI：

  10.1016/0039-128x(95)00009-f
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 、 3,3-(ethylenedioxy)-5-androsten-17β-ol 在 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 以76%的产率得到3-cycloethylenedioxy-17β-O-(tetrahydropyranyl)-androst-5-ene
  参考文献：
  名称：

  Synthesis of C-6 fluoroandrogens: Evaluation of ligands for tumor receptor imaging

  摘要：

  Seven androgens, substituted with fluorine at C-6, were prepared as potential imaging agents for androgen receptor-positive prostate tumors and were evaluated in vitro in terms of their lipophilicity and their relative binding affinities (RBA, relative to R 1881 = 100) for the androgen receptor and for sex steroid binding protein. Introduction of a fluorine atom into the C-6 position of an androgen generally decreases binding affinity to the androgen receptor, except in the two cases: 6 alpha-fluoro-19-nor-testosterone (RBA = 41.6 versus 30.6 for the unsubstituted steroid) and 6 alpha-fluoro-19-nor-testosterone (RBA = 8.9 versus 6.6). Receptor binding of the C-6 fluoro-androgens is also stereospecific, showing higher binding affinities for the alpha-epimers compared to the corresponding beta-epimers (4:1-15:1). Binding affinity to sex steroid binding protein is the lowest with 19-nor-testosterone, which is also the least lipophilic androgen studied. Based on the binding properties of compounds in this series, 6 alpha-fluoro-19-nor-testosterone appears to have the most promise as a turner imaging agent.

  DOI：

  10.1016/0039-128x(95)00009-f

文献信息

• Cleavage of Acetals Promoted by Copper (II) Sulphate Adsorbed on Silica Gel
  作者：G. M. Caballero、E. G. Gros

  DOI：10.1080/00397919508011371

  日期：1995.2

  Copper sulphate supported on silica gel promotes the easy removal of cyclic acetals and tetrahydropyranyl ethers to give the respective parent carbonyl and hydroxyl compounds.