3-hydroxy-4-methylestra-1,3,5(10)-trien-17-one | 68969-90-4

• 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-hydroxy-4-methylestra-1,3,5(10)-trien-17-one
• 英文别名: 4-Methyl-oestron；4-Methylestrone；(8R,9S,13S,14S)-3-hydroxy-4,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
• CAS: 68969-90-4
• 化学式: C₁₉H₂₄O₂
• 分子量: 284.398
• InChiKey: ZHKWXIUEKZTDQH-JEWRLFTDSA-N

物化性质

• 熔点：
  >126oC (dec.)
• 溶解度：
  氯仿（微溶）、乙酸乙酯（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-hydroxy-4-methylestra-1,3,5(10)-trien-17-one 在 palladium diacetate 、 2,6-二叔丁基-4-甲基吡啶 、 三苯基膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成 N,N-diisopropyl-3-<<(trifluoromethyl)sulfonyl>oxy>-4-methylestra-1,3,5(10),16-tetraene-17-carboxamide
  参考文献：
  名称：

  Steroidal A ring aryl carboxylic acids: a new class of steroid 5.alpha.-reductase inhibitors

  摘要：

  A series of 17 beta-carbamoyl-1,3,5(10)-estratriene-3-carboxylic acids has been prepared and evaluated in vitro as inhibitors of human and rat prostatic steroid 5 alpha-reductase (EC 1.3.1.30). Potent inhibition of the human enzyme, in particular, was observed and preliminary studies using rat enzyme suggest that the inhibition results from the formation of an enzyme-NADP(+)-inhibitor complex. The compounds were synthesized from estrone, generally employing a differentiated bis-triflate carbonylation strategy.

  DOI：

  10.1021/jm00165a009
• 作为产物：
  描述：

  4-methyl-4-estrene-3,17-dione 生成 3-hydroxy-4-methylestra-1,3,5(10)-trien-17-one
  参考文献：
  名称：

  HOLT, DENNIS A.;LEVY, MARK A.;LADD, DAVID L.;OH, HYE-JA;ERB, JILL M.;HEAS+, J. MED. CHEM., 33,(1990) N, C. 937-942

  摘要：

  DOI：

文献信息

• The Synthesis of 2-and 4-Alkoxymethylestrogens.
  作者：Hidehiko Kaneko、Masahisa Hashimoto、Akio Kobayashi

  DOI：10.1248/cpb.12.196

  日期：——

  2-Dimethylaminomethylestrone (Ia) and the 4-isomer (IIa) were obtained from the Mannich product of estrone. Methiodides of I'a-c and II'a-c were treated with alcoholic alkali to give 2-and 4-alkoxymethylestrogens in good yields. Methylation in the usual manner of I and II failed, but reaction of I and II with dimethylsulfate in a boiling methanolic alkali gave the 3-methyl ethers of 2-and 4-methoxymethylestrogens, respectively. The structural assignments of the isomers were discussed based on nuclear magnetic resonance, infrared and ultraviolet spectra.

  2-二甲氨基甲基雌酮 (Ia) 和其4-异构体 (IIa) 通过雌酮的曼尼希产物获得。I'a-c 和 II'a-c 的碘甲基化衍生物与醇性碱反应，良好产率地得到了2-和4-烷氧基甲基雌激素。对I和II的常规甲基化反应未成功，但I和II与二甲基硫酸酯在沸腾的甲醇碱中反应，分别得到了2-和4-甲氧基甲基雌激素的3-甲基醚。根据核磁共振、红外和紫外光谱，讨论了这些异构体的结构指派。
• Modified, hydroxy-substituted aromatic structures having cytoprotective activity
  申请人：Covey Douglas F.

  公开号：US09156876B2

  公开（公告）日：2015-10-13

  The present invention is directed to a process for conferring cytoprotection on a population of cells which comprises administering to that population of cells a compound comprising a hydroxy-substituted aromatic ring structure and a non-fused polycyclic, hydrophobic substituent attached thereto. In particular, the present invention is directed to such a process wherein the administered compound is phenolic, such as a steriod (e.g., estrogen), and has a non-fused polycyclic, hydrophobic substituent attached to the hydroxy-substituted A-ring thereof.

  本发明涉及一种为细胞群体提供细胞保护作用的过程，包括向该细胞群体施用一种包含一个氢氧基取代芳环结构和一个与之相连的非融合多环疏水取代基的化合物。具体来说，本发明涉及一种这样的过程，其中所施用的化合物是酚类的，例如类固醇（例如雌激素），并且具有一个与其氢氧基取代A环相连接的非融合多环疏水取代基。
• MODIFIED, HYDROXY-SUBSTITUTED AROMATIC STRUCTURES HAVING CYTOPROTECTIVE ACTIVITY
  申请人：Covey F. Douglas

  公开号：US20060009438A2

  公开（公告）日：2006-01-12

  Abstract of the Disclosure The present invention is directed to a process for conferring cytoprotection on a population of cells which comprises administering to that population of cells a compound comprising a hydroxy-substituted aromatic ring structure and a non-fused polycyclic, hydrophobic substituent attached thereto. In particular, the present invention is directed to such a process wherein the administered compound is phenolic, such as a steriod (e.g., estrogen), and has a non-fused polycyclic, hydrophobic substituent attached to the hydroxy-substituted A-ring thereof.

  本发明涉及一种用于给细胞群体提供细胞保护的方法，该方法包括向该细胞群体中投与一种化合物，所述化合物包含一个羟基取代的芳香环结构和一个附着于其上的非融合多环、疏水取代基。特别地，本发明涉及一种这样的方法，其中所投与的化合物为酚类，例如类固醇（例如雌激素），并且具有附着于其羟基取代的A环上的非融合多环、疏水取代基。
• Verfahren zur schnellen thermischen Anregung einer chemischen Reaktion in einer überkritisch fluiden Lösung
  申请人：Buback, Michael, Prof. Dr.

  公开号：EP1247566A1

  公开（公告）日：2002-10-09

  Bei einem Verfahren zur schnellen thermischen Anregung einer chemischen Reaktion in einer Lösung, die sich während der Reaktion in überkritisch fluidem Zustand befindet, wird ein Fluid auf eine Fluidtemperatur aufgeheizt, die oberhalb einer Reaktionstemperatur liegt, wobei die Zusammensetzung des Fluids so abgestimmt ist, daß das Fluid bei der Fluidtemperatur stabil ist und nicht abgebaut wird, dann wird das Fluid mit mindestens einem Reaktionspartner der gewünschten Reaktion vermischt, der sich zuvor auf einer Vorreaktionstemperatur unterhalb der Reaktionstemperatur befindet, wobei die Lösung entsteht und der Reaktionspartner binnen einem Zeitraum auf die Reaktionstemperatur gebracht wird, der kürzer als die Halbwertszeit der gewünschten Reaktion bei der Reaktionstemperatur ist.

  一种在反应期间处于超临界流体状态的溶液中快速热激发化学反应的方法，是将流体加热到高于反应温度的流体温度，调整流体的成分，使流体在流体温度下稳定而不降解、然后将流体与所需反应的至少一种反应物混合，该反应物之前处于低于反应温度的预反应温度下，由此形成溶液，并在比所需反应在反应温度下的半衰期更短的时间内将反应物带到反应温度。
• Synthesis of 4-Formyl Estrone Using a Positional Protecting Group and Its Conversion to Other C-4-Substituted Estrogens
  作者：Yong Liu、Byoungmoo Kim、Scott D. Taylor

  DOI：10.1021/jo7017075

  日期：2007.11.1

  [GRAPHICS]4-Formyl estrone was synthesized in overall good yield in three steps starting from estrone. This was achieved by conducting an electrophilic aromatic substitution reaction using formaldehyde, triethylamine, and MgCl2 on 2-tert-butyl estrone, which was readily prepared in 96% yield from estrone using tertbutyl alcohol and BF3OEt2. The tert-butyl group acted as a positional protecting group to prevent reaction at the 2-position. The tert-butyl group was readily removed in good yield using AlCl3 in dichloromethane/CH3NO2. To our knowledge, this represents the first use of a positional protecting group for the synthesis of a C-4-modified estrogen. 4-Formyl estrone was used as a common precursor to obtain a variety of other C-4 modified estrogens in very high yields such as 4-methylestrone and 4-hydroxymethylestrone as well as the novel estrogen 4-carboxyestrone. The syntheses of 4-formyl, -methyl-, and -hydroxymethyl estrone represent dramatic improvements over previously reported syntheses of these compounds.