16α-acetoxymethyl-3-benzyloxyestra-1,3,5(10)-trien-17β-ol | 438536-65-3

• 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: 16α-acetoxymethyl-3-benzyloxyestra-1,3,5(10)-trien-17β-ol
• CAS: 438536-65-3
• 化学式: C₂₈H₃₄O₄
• 分子量: 434.576
• InChiKey: DHZIMTLLTHXNCD-LDUAKDNISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.27
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  16α-acetoxymethyl-3-benzyloxyestra-1,3,5(10)-trien-17β-ol 在 palladium on activated charcoal 吡啶 、 chromium(VI) oxide 、 lithium aluminium tetrahydride 、 硫酸 、 氢气 、 sodium methylate 、 叔丁醇 作用下， 以 甲醇 、 乙醚 、 乙醇 、 丙酮 为溶剂， 20.0 ℃ 、2.0 MPa 条件下， 反应 40.0h， 生成 16α-hydroxymethylestra-1,3,5(10)-trien-3,17α-ol
  参考文献：
  名称：

  Synthesis and receptor-binding examination of 16-hydroxymethyl-3,17-estradiol stereoisomers

  摘要：

  The four 16-hydroxyniethylestra-1,3,5(10)-triene-3,17-diol isomers were synthesized and tested in a radioligand-binding assay. The estrogen receptor recognizes these compounds, but their relative binding affinities are lower than 2.0% relative to that of the reference molecule estra-1,3,5(10)-triene-3,17beta-diol. The affinities of the tested compounds for the androgen and progesterone receptors are very low (K-i > 100 mum and 1 muM, respectively). The prepared 16-hydroxymethylestra-1,3,5(10)-triene-3,17-diol isomers are therefore estrogen receptor-selective molecules. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(01)00191-x
• 作为产物：
  描述：

  16-hydroxymethylene-3-benzyloxyestra-1,3,5(10)-trien-17-one 在 吡啶 、 钾硼氢 作用下， 以 乙醇 为溶剂， 反应 27.0h， 生成 16α-acetoxymethyl-3-benzyloxyestra-1,3,5(10)-trien-17β-ol
  参考文献：
  名称：

  Synthesis and receptor-binding examination of 16-hydroxymethyl-3,17-estradiol stereoisomers

  摘要：

  The four 16-hydroxyniethylestra-1,3,5(10)-triene-3,17-diol isomers were synthesized and tested in a radioligand-binding assay. The estrogen receptor recognizes these compounds, but their relative binding affinities are lower than 2.0% relative to that of the reference molecule estra-1,3,5(10)-triene-3,17beta-diol. The affinities of the tested compounds for the androgen and progesterone receptors are very low (K-i > 100 mum and 1 muM, respectively). The prepared 16-hydroxymethylestra-1,3,5(10)-triene-3,17-diol isomers are therefore estrogen receptor-selective molecules. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(01)00191-x