6-Dehydromethyltestosterone | 5585-85-3

• 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: 6-Dehydromethyltestosterone
• 英文别名: 17β-hydroxy-17α-methyl-androsta-4,6-dien-3-one；17β-Hydroxy-17α-methyl-androsta-4,6-dien-3-on；17β-Hydroxy-17α-methyl-Δ^4.6-androstadienon-(3)；17alpha-Methyl-6,7-dehydrotestosterone；(8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13,17-trimethyl-2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-3-one
• CAS: 5585-85-3
• 化学式: C₂₀H₂₈O₂
• 分子量: 300.441
• InChiKey: BRQAXEKVGOTNJM-HLXURNFRSA-N

物化性质

• 熔点：
  196.0-197.6 °C
• 沸点：
  450.4±45.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)
• 溶解度：
  乙腈（微溶）、氯仿（微溶）、甲醇（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  6-Dehydromethyltestosterone 在 四氢呋喃 、 copper(I) chloride 、 氨 、 lithium 作用下， 生成 卡普睾酮
  参考文献：
  名称：

  The Synthesis of Some 7α- and 7β-Methyl Steroid Hormones¹

  摘要：

  DOI：

  10.1021/ja01524a063
• 作为产物：
  描述：

  17-甲睾酮 在 human P₄₅₀ 3A₄ monooxygenase 作用下， 以 甲醇 、 aq. phosphate buffer 、 二甲基亚砜 为溶剂， 反应 24.0h， 以1%的产率得到6-Dehydromethyltestosterone
  参考文献：
  名称：

  使用人 P450 3A4 通过一步生物催化实现天然产物多样化

  摘要：

  全力以赴：在这项研究中，成功​​探索了人类细胞色素 P450 3A4 作为基于毕赤酵母的全细胞生物催化剂在天然产物多样化方面的合成潜力。以 100 mg 的制备规模分离了六种选定天然产物的总共 31 种真实人体代谢物，其中许多是第一次，揭示了前所未有的多样化程度。

  DOI：

  10.1002/cctc.202101564

文献信息

• 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.
• Esters of Some Steroidal 3β-Hydroxy-4,6-dienes and their Biological Activity
  作者：John S. Baran

  DOI：10.1021/jm00339a027

  日期：1963.5
• Imitation of phase I oxidative metabolism of anabolic steroids by titanium dioxide photocatalysis
  作者：Miina Ruokolainen、Minna Valkonen、Tiina Sikanen、Tapio Kotiaho、Risto Kostiainen

  DOI：10.1016/j.ejps.2014.08.009

  日期：2014.12

  The aim of this study was to investigate the feasibility of titanium dioxide (TiO2) photocatalysis for oxidation of anabolic steroids and for imitation of their phase I metabolism. The photocatalytic reaction products of five anabolic steroids were compared to their phase I in vitro metabolites produced by human liver microsomes (HLM). The same main reaction types - hydroxylation, dehydrogenation and combination of these two - were observed both in TiO2 photocatalysis and in microsomal incubations. Several isomers of each product type were formed in both systems. Based on the same mass, retention time and similarity of the product ion spectra, many of the products observed in HLM reactions were also formed in TiO2 photocatalytic reactions. However, products characteristic to only either one of the systems were also formed. In conclusion, TiO2 photocatalysis is a rapid, simple and inexpensive method for imitation of phase I metabolism of anabolic steroids and production of metabolite standards. (C) 2014 Elsevier B.V. All rights reserved.
• Kocor,M. et al., Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques, 1973, vol. 21, # 10, p. 721 - 727
  作者：Kocor,M. et al.

  DOI：——

  日期：——
• US3931167A
  申请人：——

  公开号：US3931167A

  公开（公告）日：1976-01-06