(17R)-3-甲氧基-19-去甲孕甾-1,3,5(10),20-四烯-17-醇 | 6885-48-9

• 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: (17R)-3-甲氧基-19-去甲孕甾-1,3,5(10),20-四烯-17-醇
• 英文名称: 17β-hydroxy-3-methoxy-17α-vinylestra-1,3,5(10)-triene
• 英文别名: 17α-Vinyl-oestradiol-3-methylether；3-methoxy-19-nor-17βH-pregna-1,3,5(10),20-tetraen-17-ol；(8R)-17c-Hydroxy-3-methoxy-13c-methyl-17t-vinyl-(8rH,9tH,14tH)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren；Methyl-[17β-hydroxy-17α-vinyl-oestratrien-(1,3,5(10))-yl-(3)]-aether；3-Methoxy-17α-vinyl-oestratrien-(1,3,5(10))-ol-(17β)；3-Methoxy-17α-vinyl-oestratrien-(A)-ol-(17β)；(8R,9S,13S,14S,17R)-17-ethenyl-3-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ol
• CAS: 6885-48-9
• 化学式: C₂₁H₂₈O₂
• 分子量: 312.452
• InChiKey: BFJGDRRSEQORFA-MJCUULBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (17R)-3-甲氧基-19-去甲孕甾-1,3,5(10),20-四烯-17-醇 在 四氧化锇 、 双氧水 、 叔丁醇 作用下， 生成 17,21-dihydroxy-3-methoxy-19-nor-pregna-1,3,5(10)-trien-20-one
  参考文献：
  名称：

  17-glycolyl-estradiols

  摘要：

  公开号：

  US02666769A1
• 作为产物：
  描述：

  炔雌醇 在 吡啶 、 氢氧化钾 、 palladium on activated charcoal 、 Lindlar's catalyst 作用下， 生成 (17R)-3-甲氧基-19-去甲孕甾-1,3,5(10),20-四烯-17-醇
  参考文献：
  名称：

  The Preparation of Two Aromatic Analogs of Desoxycorticosterone Acetate

  摘要：

  DOI：

  10.1021/ja01180a022

文献信息

• Synthese vonracem-3-Methoxy-17β-hydroxy-1.3.5(10)-östratrien-17α-carbonsäure und 3-Methoxy-17α-hydroxy-1.3.5(10)-östratrien-17β-carbonsäure
  作者：Klaus Prezewowsky、Rudolf Wiechert、Walter Hohlweg

  DOI：10.1002/jlac.19717520110

  日期：1971.10.29

  Es werden Methoden zur Darstellung der Titelverbindungen 1a und 2a sowie deren Methylester 1b und 2b beschrieben. Die pharmakologischen Wirkungen der Verbindungen 1a und 2a werden angegeben.

  Es werden Methoden zur Darstellung der Titelverbindungen 1a和2a sowie deren甲酯1b和2b beschrieben。药房是1a和2a werden angegeben。
• Vanadium (IV) chloride induced allylic rearrangement of a steroidal alcohol
  作者：A. Krubiner、A. Perrotta、H. Lucas、E.P. Oliveto

  DOI：10.1016/s0039-128x(72)80030-8

  日期：1972.5

  Abstract 17-α-Vinylestradiol 3-methyl ether 1 undergoes allylic rearrangement in the presence of vanadium (IV) chloride to produce a Δ17(20)-21-chloride 2 in high yield. The latter compound can be converted to the 21-acetoxy-17α-hydroxy-20-keto side-chain by two different routes.

  摘要 17-α-乙烯基雌二醇 3-甲基醚 1 在氯化钒 (IV) 存在下发生烯丙基重排，以高产率生成 Δ17(20)-21-氯化物 2。后一种化合物可以通过两种不同的途径转化为 21-乙酰氧基-17α-羟基-20-酮侧链。
• ——
  作者：R. P. Litvinovskaya、S. V. Drach、Yu. I. Lapchinskaya、V. A. Khripach

  DOI：10.1023/a:1012317215582

  日期：——

  1,3-Dipolar cycloaddition of nitrile oxides to 17 beta -hydroxy-17 alpha -vinyl steroids of the estrone series proceeds both regio- and stereoselectively. The stereoselectivity of the process decreases in going to steroids of the androstane series. The major epimer has S configuration of the new chiral center.
• Lehmann,H.-G. et al., Chemische Berichte, 1965, vol. 98, p. 1470 - 1475
  作者：Lehmann,H.-G. et al.

  DOI：——

  日期：——
• Synthesis, receptor binding, and tissue distribution of (17.alpha.,20E)- and (17.alpha.,20Z)-21-[125I]Iodo-19-norpregna-1,3,5-(10),20-tetraene-3,17-diol
  作者：H. Ali、J. Rousseau、M. A. Ghaffari、J. E. Van Lier

  DOI：10.1021/jm00118a013

  日期：1988.10

  The isomeric (17 alpha,20E)- and (17 alpha,20Z)-(iodovinyl)estradiol derivatives 3 and 6, and their no-carrier-added (nca) [125I]iodovinyl analogues, were tested for their relative target tissue retention and binding affinity for the estrogen receptor. The (iodovinyl)estradiols 3 and 6 were prepared via destannylation of the (17 alpha,20E)- and (17 alpha,20Z)-tributylstannyl precursors 2 and 4 with retention of configuration. Selective formation of the E or Z isomers 2 and 4 during the reaction of 17 alpha-ethynylestradiol 1a with tri-n-butyltin hydride was controlled by the presence or absence of the catalyst, the polarity of the solvent, and the reaction temperature. The nca [125I]iodovinyl analogues [125I]-3a and [125I]-6a were obtained in good radiochemical yield and high purity by treatment of 2a and 4a with [125I]NaI in the presence of H2O2 and chloroamine-T, respectively. Of the two isomeric iodovinyl derivatives 3 and 6, the 20Z isomer 6a exhibited the highest receptor binding affinity and the [125I]-6a gave the highest in vivo receptor-mediated target tissue uptake.