androsta-4,6-diene-3,11,17-trione | 50718-37-1

• 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: androsta-4,6-diene-3,11,17-trione
• 英文别名: Androstadien-4,6-trion-3,11,17；(8S,9S,10R,13S,14S)-10,13-dimethyl-1,2,8,9,12,14,15,16-octahydrocyclopenta[a]phenanthrene-3,11,17-trione
• CAS: 50718-37-1
• 化学式: C₁₉H₂₂O₃
• 分子量: 298.382
• InChiKey: JJKJPXNLLLTMNV-IRIMSJTPSA-N

物化性质

• 熔点：
  242-244 °C
• 沸点：
  497.8±45.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  22
• 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：
  51.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  二甲基硫 、 androsta-4,6-diene-3,11,17-trione 在 盐酸 、 甲基锂 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以36%的产率得到7α-Methylandrost-4-ene-3,11,17-trione
  参考文献：
  名称：

  Androgenic steroid compounds and a method of making and using the same

  摘要：

  一种雄激素类固醇化合物，其化学式为：##STR1## 其中：X、Y、Z、R.sup.1、R.sup.2、R.sup.3、R.sup.5 和 R.sup.6 的定义如本文所述。

  公开号：

  US05952319A1
• 作为产物：
  描述：

  肾上腺甾酮 在 氩 、 2,3-dichloro-5,6-dicyanoquionone 、 dihydro-DDQ 、 1,4-二氧六环 、 silica gel 作用下， 以 1,4-二氧六环 、 盐酸 为溶剂， 反应 1.5h， 生成 androsta-4,6-diene-3,11,17-trione
  参考文献：
  名称：

  Androgenic steroid compounds and a method of making and using the same

  摘要：

  这是一种雄激素类固醇化合物，其化学式为：其中，X、Y、Z、R1、R2、R3、R5和R6如本文所定义。

  公开号：

  US06864248B2

文献信息

• Process for the production of 7alpha-methyl steroids
  申请人：Schering AG

  公开号：US20040010138A1

  公开（公告）日：2004-01-15

  This invention relates to a process for the production of 7&agr;-methyl steroids of general formula I, 1 starting from compounds of general formula II, 2 which are reacted in an aprotic solvent in the presence of 1-30 mol % of a copper compound CuY n L m with 1-3 molar equivalents of CH 3 MgX, then with a strong acid. The process according to the invention is distinguished in that 7&agr;-methyl steroids are obtained in good yields as well as high chemical purity and high diastereomer purities. The process is distinguished in that less waste accumulates with considerably higher throughput. The process according to the invention can therefore be suitable for the production of 7&agr;-methyl steroids on the industrial scale.

  这项发明涉及一种从通式II的化合物出发，在无水溶剂中与1-30摩尔％的铜化合物CuYnLm和1-3摩尔当量的CH3MgX反应，然后与强酸反应，生产通式I的7α-甲基类固醇的过程。根据本发明的方法在于获得良好收率、高化学纯度和高对映体纯度的7α-甲基类固醇。该方法的独特之处在于废物积累较少，且产量明显更高。因此，根据本发明的方法可能适用于工业规模上生产7α-甲基类固醇。
• [EN] ANDROGENIC STEROID COMPOUNDS AND A METHOD OF MAKING AND USING THE SAME<br/>[FR] COMPOSES DE STEROIDES ANDROGENES ET PROCEDE DE FABRICATION ET D'UTILISATION DE CEUX-CI
  申请人：RESEARCH TRIANGLE INSTITUTE

  公开号：WO1999026962A1

  公开（公告）日：1999-06-03

  (EN) An androgenic steroid compound of formula (I) wherein: X, Y, Z, R1, R2, R3, R5 and R6 are as defined herein.(FR) L'invention concerne un composé de stéroïde androgène représenté par la formule (I), dans laquelle X, Y, Z, R1, R2, R3, R5 et R6 sont tels que définis dans la demande.

  一种雄激素类固醇化合物，其分子式为（I），其中：X、Y、Z、R1、R2、R3、R5和R6的定义如本申请所述。
• ANDROGENIC STEROID COMPOUNDS AND A METHOD OF MAKING AND USING THE SAME
  申请人：——

  公开号：US20020002156A1

  公开（公告）日：2002-01-03

  An androgenic steroid compound of the formula: 1 wherein: X, Y, Z, R 1 , R 2 , R 3 , R 5 and R 6 are as defined herein.

  一种雄激素类固醇化合物，其化学式为：1，其中X、Y、Z、R1、R2、R3、R5和R6如此处所定义。
• Antiprogestational agents. The synthesis of 7-alkyl steroidal ketones with anti-implantational and antidecidual activity
  作者：Joyce F. Grunwell、Harvey D. Benson、J.O'Neal Johnston、Vladimir Petrow

  DOI：10.1016/0039-128x(76)90136-7

  日期：1976.6

  A series of 7alpha- and 7beta- alkyl derivatives of steroidal 4-en- and 5-en-3-ones were prepared by 1,6-conjugate addition of organocopper reagents to various steroidal 4,6-dien-3-ones of the androstane, estrane and gonane series. Biological study of these and related compounds revealed that 17beta-hydroxy-7alpha-methyl-5-androsten-3-one (2), 17beta-hydroxy-7alpha-methyl-5-estren-3-one acetate and 17beta-hydroxy-7alpha-methyl-4-estren-3-one acetate had significant anti-implantational and antidecidual activities. The contragestative effects were associated with the latter anti-hormonal properties, and not with the androgenicity of these compounds.
• Stereoselective synthesis of some methyl-substituted steroid hormones and their in vitro cytotoxic activity against human gastric cancer cell line MGC-803
  作者：Chun Li、Wenwei Qiu、Zhengfeng Yang、Jian Luo、Fan Yang、Mingyao Liu、Juan Xie、Jie Tang

  DOI：10.1016/j.steroids.2010.05.008

  日期：2010.12

  A series of 3-, 7-, 15-, and 16-methyl-substituted steroid analogs were synthesized via a highly stereoselective 1,6-conjugate addition. Under the catalysis of CuBr, AlMe(3) reacted with four steroid dienone precursors to afford either the corresponding et-epimer of C-3 and C-7 methyl-substituted steroids as the major products, and the ratio of 43 was up to alpha/beta. No beta-epimer has been detected for methyl addition at C-16. However, under the same reaction conditions, enantioselective methyl addition at C-15 afforded the 15 beta-epimer as the major product. The preliminary SAR analysis showed that the methyl substituents at C-7 alpha and C-15 beta positions lead to a dramatical increase in potency against human gastric cancer cell line MGC-803. (C) 2010 Elsevier Inc. All rights reserved.