estradiol 17β-tetrahydropyranyl ether | 3589-90-0

• 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: estradiol 17β-tetrahydropyranyl ether
• 英文别名: 17β-O-(tetrahydropyranyl)estradiol；17beta-Estradiol 3-tetrahydropyranyl ether；(8R,9S,13S,14S,17S)-13-methyl-17-(oxan-2-yloxy)-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-ol
• CAS: 3589-90-0
• 化学式: C₂₃H₃₂O₃
• 分子量: 356.505
• InChiKey: DRRJWMXJIVWKKW-CUFSGNDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  estradiol 17β-tetrahydropyranyl ether 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 雌二醇
  参考文献：
  名称：

  Al-Hassan, Mohammed I., Synthetic Communications, 1989, vol. 19, # 3and4, p. 453 - 462

  摘要：

  DOI：
• 作为产物：
  描述：

  诺龙 在 双氧水 、 lithium diisopropyl amide 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 3.67h， 生成 estradiol 17β-tetrahydropyranyl ether
  参考文献：
  名称：

  Al-Hassan, Mohammed I., Synthetic Communications, 1989, vol. 19, # 3and4, p. 453 - 462

  摘要：

  DOI：

文献信息

• Proton and carbon-13 nuclear magnetic resonance spectroscopy of diastereoisomeric 3- and 17β-tetrahydropyranyl ether derivatives of estrone and estradiol
  作者：Vincent Boucheau、Mélanie Renaud、Marc Rolland de Ravel、Elisabeth Mappus、Claude Y. Cuilleron

  DOI：10.1016/0039-128x(90)90018-7

  日期：1990.5

  Protection of 3- and 17 beta-hydroxyl groups of estrone and estradiol as tetrahydropyranyl ether derivatives led to mixtures of 2'(R)- and 2'(S)-diastereoisomers which were separated by crystallization (3-tetrahydropyranyl ethers), or by thin-layer chromatography (17-tetrahydropyranyl ethers), and characterized by 1H and 13C nuclear magnetic resonance (NMR). Assignments for NMR signals of estradiol 3,17 beta-ditetrahydropyranyl ether were facilitated by comparison with those of its 15 zeta, 16 zeta-dideuterio analog and by 2D 1H-13C heteroshift correlation experiments. Diastereoisomers of 3-tetrahydropyranyl ether derivatives could be identified through the 13C NMR doublet signals of the anomeric C-2' and the aromatic C-4 carbon atoms in CDCl3. Diastereoisomers of 17-tetrahydropyranyl ether derivatives were recognized from characteristic modifications of 1H NMR signals of H-2', H-6', H-1, H-17, and 18-CH3 protons as well as from the 13C NMR doublet signals corresponding to C-2', C-4', C-6', C-12, C-13, C-16, and C-17 carbon atoms. Low-temperature experiments showed a splitting of the C-2', C-6', and C-17 13C NMR signals of each of the two 17-tetrahydropyranyl ether isomers. The downfield signal (equatorial conformer) of the three resulting doublets was more intense for the 17-tetrahydropyranyl ether 2'(S)-isomer, whereas the upfield signal (axial conformer) was more intense for the 2'(R)-isomer.
• Mechanistic studies on a placental aromatase model reaction
  作者：Philip A. Cole、Cecil H. Robinson

  DOI：10.1021/ja00021a044

  日期：1991.10

  Aromatase is a cytochrome P-450 enzyme that converts androgens to estrogens via three successive oxidative reactions. The mechanism of the third step has previously been intensively studied, with no clear resolution. A leading theory for the third step proposes nucleophilic attack of the heme ferric peroxide species on the 19-aldehyde intermediate to produce a 19-hydroxy 19-ferric peroxide intermediate. We have shown previously that analogues of this intermediate failed to aromatize under nonenzymatic conditions. In this study, we prepared a 2,4-dien-3-ol analogue of the 19-aldehyde intermediate and showed that it reacted with HOOH to produce the corresponding estrogen derivative. Evidence has been accrued to suggest that this reaction, which we have called the aromatase model reaction, involves a 19-hydroxy 19-hydroperoxide intermediate. The model reaction was shown to be faithful to the actual aromatase-catalyzed reaction with regard to stoichiometric formic acid production, O-18-incorporation patterns, and stereoselectivity for 1-beta-hydrogen removal. A kinetic analysis at 37-degrees-C was also performed, and the reaction was demonstrated to be pseudo-first-order by using an excess of HOOH, and first-order with respect to HOOH at the concentrations studied. The effects of KOH, EDTA, and BHT on the reaction were also examined, and are discussed.
• Al-Hassan, Mohammed I., Synthetic Communications, 1989, vol. 19, # 3and4, p. 453 - 462
  作者：Al-Hassan, Mohammed I.

  DOI：——

  日期：——