4-(4-(((8R,9S,13S,14S,17S)-3,17-dihydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl)ethynyl)phenyl)butanal | 1215455-18-7

• 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: 4-(4-(((8R,9S,13S,14S,17S)-3,17-dihydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl)ethynyl)phenyl)butanal
• CAS: 1215455-18-7
• 化学式: C₃₀H₃₄O₃
• 分子量: 442.598
• InChiKey: MAIAYYQKYVXXAW-ZNOUKXQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.55
• 重原子数：
  33.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  57.53
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  炔雌醇 、 4-(4-iodophenyl)butyraldehyde 在 tris-(dibenzylideneacetone)dipalladium(0) 、 copper(l) iodide 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以60%的产率得到4-(4-(((8R,9S,13S,14S,17S)-3,17-dihydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl)ethynyl)phenyl)butanal
  参考文献：
  名称：

  Click synthesis of estradiol–cyclodextrin conjugates as cell compartment selective estrogens

  摘要：

  Cyclodextrin (CD) is a well known drug carrier and excipient for enhancing aqueous solubility. CDs themselves are anticipated to have low membrane permeability because of relatively high hydrophilicity and molecular weight. CD derivatization with 17-beta estradiol (E-2) was explored extensively using a number of different click chemistries and the cell membrane permeability of synthetic CD-E-2 conjugate was explored by cell reporter assays and confocal fluorescence microscopy. In simile with reported dendrimer-E-2 conjugates, CD-E-2 was found to be a stable, extranuclear receptor selective estrogen that penetrated into the cytoplasm. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.11.046