9beta-Estradiol | 5864-38-0

• 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: 9beta-Estradiol
• 英文别名: (9β)-estra-1,3,5(10)-triene-3,17β-diol；β-estradiol；9-Iso-oestradiol；9-iso-estradiol；Dihydrofolliculin,(S)；(8R,9R,13S,14S,17S)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
• CAS: 5864-38-0
• 化学式: C₁₈H₂₄O₂
• 分子量: 272.387
• InChiKey: VOXZDWNPVJITMN-ADHGMGHFSA-N

物化性质

• 熔点：
  223 °C
• 沸点：
  445.9±45.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  雄甾-1,4,9(11)-三烯-3,17-二酮 在 potassium fluoride 、 sodium hydroxide 、 sodium tetrahydroborate 、 六甲基二硅氧烷 、 对甲苯磺酸 、 硅烷 作用下， 以 甲醇 、 二氯甲烷 、 乙二醇 为溶剂， 反应 2.0h， 生成 9beta-Estradiol
  参考文献：
  名称：

  An environmentally friendly and cost effective synthesis of estradiol featuring two novel reagents: Si(0)/KF and PMHS/hexamethyldisiloxane/pTSA

  摘要：

  Si(O)/KF is introduced as a strong, inexpensive, environmentally friendly, and safe reagent for 'dissolving metal'-type reduction. PMHS/hexamethyldisiloxane/pTSA is introduced as an inexpensive substitute for Et3SiH/TFA for 'ionic hydrogenation', where the hexamethyldisiloxane functions as a capping agent to block the oligomeric silicone by-product from cross-linking to a gel, rubber, or plastic. An environmentally friendly and cost effective synthesis of estradiol is described which showcases these new reagents. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.06.136

文献信息

• Structure-activity relationships of 9β-estrogens
  作者：R. Bruce Gabbard、Albert Segaloff

  DOI：10.1016/0039-128x(83)90119-8

  日期：1983.11

  The 9 beta isomers of estradiol-17 beta, estradiol-17 a estrone and 17-ethinylestradiol-17 beta were synthesized and compared with their 9a-counterparts in the rat uterine cytosol estrogen receptor, uterotropic, and gonadotropin release inhibition assays. Except for 17-ethinyl-9 beta-estradiol-17 beta which was as active as its 9a isomer in the uterotropic assay, none of the 9 beta estrogens exhibited any biological activity which was equal to or greater than their 9a counterparts. For examples, 9 beta-estradiol-17 beta was 1/10 as active as estradiol-17 beta, and 9 beta-estrone was 1/4 as active as estrone in the uterotropic assay.
• An environmentally friendly and cost effective synthesis of estradiol featuring two novel reagents: Si(0)/KF and PMHS/hexamethyldisiloxane/pTSA
  作者：Chongsoo Lim、Gerald N. Evenson、William R. Perrault、Bruce A. Pearlman

  DOI：10.1016/j.tetlet.2006.06.136

  日期：2006.9

  Si(O)/KF is introduced as a strong, inexpensive, environmentally friendly, and safe reagent for 'dissolving metal'-type reduction. PMHS/hexamethyldisiloxane/pTSA is introduced as an inexpensive substitute for Et3SiH/TFA for 'ionic hydrogenation', where the hexamethyldisiloxane functions as a capping agent to block the oligomeric silicone by-product from cross-linking to a gel, rubber, or plastic. An environmentally friendly and cost effective synthesis of estradiol is described which showcases these new reagents. (c) 2006 Elsevier Ltd. All rights reserved.