7α-methyl-17β-hydroxy-4-androsten-3-one | 7642-58-2

• 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: 7α-methyl-17β-hydroxy-4-androsten-3-one
• 英文别名: 7α-methyltestosterone；17β-hydroxy-7α-methyl-androst-4-en-3-one；17β-Hydroxy-7α-methyl-androst-4-en-3-on；7α-methyl-19-nortestosterone；7-α-methyl testosterone；7α-Methyl-17β-hydroxyandrost-4-en-3-on；7alpha-Methyltestosterone；(7R,8R,9S,10R,13S,14S,17S)-17-hydroxy-7,10,13-trimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS: 7642-58-2
• 化学式: C₂₀H₃₀O₂
• 分子量: 302.457
• InChiKey: HZWZHWTZLZZBFF-UQYBFTDGSA-N

物化性质

• 熔点：
  211-214 °C
• 沸点：
  438.9±45.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 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：

  7α-methyl-17β-hydroxy-4-androsten-3-one 反应 2.0h， 生成 (7S,8R,9S,10R,13S,14S)-3,7,10,13-Tetramethyl-1,2,7,8,9,10,11,12,13,14,15,16-dodecahydro-cyclopenta[a]phenanthren-17-one
  参考文献：
  名称：

  甾体3,5-二烯。

  摘要：

  DOI：

  10.1021/jm00234a009
• 作为产物：
  描述：

  睾酮 在 盐酸 、 对甲苯磺酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 苯 为溶剂， 生成 7α-methyl-17β-hydroxy-4-androsten-3-one
  参考文献：
  名称：

  Antiprogestational agents. The synthesis of 7-alkyl steroidal ketones with anti-implantational and antidecidual activity

  摘要：

  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.

  DOI：

  10.1016/0039-128x(76)90136-7

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。
• TRANSDERMAL ADMINISTRATION OF MENT
  申请人：——

  公开号：US20020012694A1

  公开（公告）日：2002-01-31

  The present invention relates to transdermal dosage forms for delivery of androgens.

  本发明涉及用于递送雄激素的经皮剂量形式。
• ANDROGEN AS A MALE CONTRACEPTIVE AND NON-CONTRACEPTIVE ANDROGEN REPLACEMENT
  申请人：——

  公开号：US20020193359A1

  公开（公告）日：2002-12-19

  The present invention relates to methods of providing male contraception using a specified androgen without the need of a separate sterilizing agent. The invention also describes methods for non-contraceptive androgen replacement and devices useful for carrying out both processes.

  本发明涉及使用指定雄激素提供男性避孕的方法，无需单独的灭菌剂。本发明还描述了用于进行非避孕雄激素替代和实施两种过程的设备的方法。
• [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。