3,17β-dihydroestra-1,3,5(10)-trien-17β-yl formate | 28405-29-0

• 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: 3,17β-dihydroestra-1,3,5(10)-trien-17β-yl formate
• 英文别名: 17β-formyloxyestra-1,3,5(10)-trien-3-ol；estradiol-17β 17-formate；[(8R,9S,13S,14S,17S)-3-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] formate
• CAS: 28405-29-0
• 化学式: C₁₉H₂₄O₃
• 分子量: 300.398
• InChiKey: NFTKKIJRGGLGTJ-GFEQUFNTSA-N

物化性质

• 熔点：
  108-110 °C(Solv: hexane (110-54-3); chloroform (67-66-3))
• 沸点：
  448.4±45.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,17β-dihydroestra-1,3,5(10)-trien-17β-yl formate 在 sodium hydroxide 作用下， 以 吡啶 、 丙酮 为溶剂， 反应 0.33h， 生成 醋酸雌二醇酯
  参考文献：
  名称：

  用三乙胺-三氧化硫制备雌二醇-17β硫酸盐。

  摘要：

  雌二醇-17β与三乙胺-三氧化硫在吡啶中的反应仅在C17-羟基上单硫化，制备了17β-磺基氧基-1,3,5（10）-三烯-3-醇三乙铵盐（V） 。综合研究证实了光谱测量表明的结构归属。（分子式：参见文字）在制备17β-甲酰氧基-1,3的基础上，完成了3-磺基氧基乙酸酯1,3,5（10）-trien-17β-醇三乙铵盐（II）的合成， 5（10）-三烯-3-醇（XIII）。3-硫酸盐三乙铵盐II的融合产生了17硫酸盐三乙胺盐V。雌二醇-17β二硫酸盐的制备也已实现。

  DOI：

  10.1016/0039-128x(85)90079-0
• 作为产物：
  描述：

  雌酚酮 在 sodium tetrahydroborate 、 三氯氧磷 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 3,17β-dihydroestra-1,3,5(10)-trien-17β-yl formate
  参考文献：
  名称：

  A simple, convenient and chemoselective formylation of sterols by Vilsmeier reagent

  摘要：

  Vilsmeier reagent (DMF-POCl3) was used as an efficient formylating agent. Several sterols having sec-hydroxyl group at 3/17-position have been modified into respective formate esters. The method is simple, mild, chemoselective and provides sec-alcoholic protection in good yields. (c) 2006 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2006.03.005

文献信息

• Structure-activity relationships of estrogens: Effects of esterification of the 11β-hydroxyl group
  作者：Albert Segaloff、R.Bruce Gabbard

  DOI：10.1016/0039-128x(84)90063-1

  日期：1984.1

  Fourteen esters (formate, acetate, propionate, butyrate, hexanoate, heptanoate, and benzoate) located at C-11 of 11 beta-hydroxyesterone and 11 beta-hydroxyestradiol-17 beta were synthesized and evaluated for uterotropic and gonadotropin release inhibition in rats, as well as their ability to displace (3H) estradiol-17 beta from the rat uterine cytosolic estrogen receptor. The most potent uterotropic agent was 11 beta-formoxyestrone which was 1,625 or 2,500 times as active as 11 beta-hydroxyesterone in the uterotropic or gonadotropin release inhibition assay, respectively. 11 beta-Formoxyestrone was 7.5 times as uterotropic as estradiol-17 beta and equal to estradiol-17 beta in inhibiting gonadotropin release. However, the most potent inhibitor of gonadotropin release was 11 beta-acetoxy-estradiol-17 beta which had 133% of the activity of estradiol-17 beta, although it had only 38% of the activity of estradiol-17 beta in the uterotropic assay. Esters larger than the acetoxy group showed sharply decreased activities in either assay. Despite the high estrogenic potency of the 11-formates or 11-acetates, they were rather weak (6% to 35% as active as estradiol-17 beta) in displacing (3H) estradiol-17 beta from the rat uterine cytosolic estrogen receptor.