1-甲基雌甾-1,3,5(10),6-四烯e-3,17beta-二醇 | 10506-68-0

• 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
• 中文名称: 1-甲基雌甾-1,3,5(10),6-四烯e-3,17beta-二醇
• 英文名称: 1-methyl-estra-1,3,5(10),6-tetraene-3,17β-diol
• 英文别名: 1-Methyl-oestra-1,3,5(10),6-tetraen-3,17β-diol；1-Methylestra-1,3,5(10),6-tetraene-3,17beta-diol；(8R,9S,13S,14S,17S)-1,13-dimethyl-8,9,11,12,14,15,16,17-octahydrocyclopenta[a]phenanthrene-3,17-diol
• CAS: 10506-68-0
• 化学式: C₁₉H₂₄O₂
• 分子量: 284.398
• InChiKey: WCHXTGUTQVBYIP-QSUVVDIXSA-N

物化性质

• 沸点：
  467.7±45.0 °C(Predicted)
• 密度：
  1.174±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-甲基雌甾-1,3,5(10),6-四烯e-3,17beta-二醇 在 palladium on activated charcoal 、 乙酸乙酯 作用下， 生成 (8R,9S,13S,14S,17S)-1,13-二甲基-6,7,8,9,11,12,14,15,16,17-十氢环戊烯并[a]菲-3,17-二醇
  参考文献：
  名称：

  Steroids. VII.¹ Contribution to the Bromination of ▵⁴-3-Ketosteroids and a New Partial Synthesis of the Natural Estrogens

  摘要：

  DOI：

  10.1021/ja01166a055
• 作为产物：
  描述：

  3-acetoxy-1-methyl-estra-1,3,5(10),6-tetraen-17-one 在 lithium aluminium tetrahydride 作用下， 生成 1-甲基雌甾-1,3,5(10),6-四烯e-3,17beta-二醇
  参考文献：
  名称：

  Steroids. VII.¹ Contribution to the Bromination of ▵⁴-3-Ketosteroids and a New Partial Synthesis of the Natural Estrogens

  摘要：

  DOI：

  10.1021/ja01166a055

文献信息

• Potential steroidal antiestrogens
  作者：E. R. Clark、A. M. E. Omar、G. Prestwich

  DOI：10.1021/jm00218a022

  日期：1977.8

  A series of analogues of 17beta-estradiol has been synthesized and the compounds have been tested, using sucrose density gradient analysis, for their ability to compete with [6,7-3H]-17beta-estradiol for the estrogen-receptor protein from mouse uterine homogenates. Active compounds were also tested for antiuterotrophic activity in immature rats and/or mice. 3,17beta-Dihydroxy-6-phenylestra-1,3,5(10),6-tetraene (14) was the most active new compound in the in vitro test suppressing the binding of 17beta-estradiol by 34 and 87%, respectively, at molar ratios of 1 and 3.16. It was significantly more potent than the intermediate 6-oxoestradiol (4) which produced a 52% inhibition of binding at a molar ratio of 3.16. The thiosemicarbazone of 6-oxoestradiol (17) and the derived 3,17beta-dihydroxy-6-(2-imino-4-oxothiazolidinyl-1-imino)estra-1,3,5(10)-triene (19) produced, respectively, only 46 and 16% inhibition of binding at a molar ratio of 10. Introduction of a 1-methyl substituent into either 6-oxo or 6-phenyl compounds reduced affinity for the receptor significantly (compounds 5 and 15) and conversion of the 3-OH into a beta-dialkylaminoethoxy group virtually destroyed all binding activity (compounds 2, 6, 10, and 11). At a molar ratio of 10 compound 14 failed to suppress the uterine weight response of immature rats to 17beta-estradiol, whereas compound 15, at a molar ratio of 200, produced a significant increase in the uterine weight of immature rats but not of immature mice even at a molar ratio of 1000.
• Steroids. VII.¹ Contribution to the Bromination of ▵⁴-3-Ketosteroids and a New Partial Synthesis of the Natural Estrogens
  作者：Carl Djerassi、G. Rosenkranz、J. Romo、St. Kaufmann、J. Pataki

  DOI：10.1021/ja01166a055

  日期：1950.10