17-(1-methyl-2-propenyl)-3-(phenylmethoxy)-estra-1,3,5(10),16-tetraene | 533925-83-6

• 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: 17-(1-methyl-2-propenyl)-3-(phenylmethoxy)-estra-1,3,5(10),16-tetraene
• 英文别名: (8S,9S,13S,14S)-17-[(2S)-but-3-en-2-yl]-13-methyl-3-phenylmethoxy-6,7,8,9,11,12,14,15-octahydrocyclopenta[a]phenanthrene
• CAS: 533925-83-6
• 化学式: C₂₉H₃₄O
• 分子量: 398.588
• InChiKey: LXAPWGBTUIUALS-KXZNEODKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  17-(1-methyl-2-propenyl)-3-(phenylmethoxy)-estra-1,3,5(10),16-tetraene 在 Wilkinson's catalyst 、 氢气 、 sodium 、 正丁醇 作用下， 以 苯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 7.0h， 生成 (20S)-3-hydroxy-19,24-dinorchola-1,3,5(10),16-tetraene
  参考文献：
  名称：

  [EN] SUBSTITUTED (4'-HYDROXYPHENYL)CYCLOALKANE COMPOUNDS AND USES THEREOF AS SELECTIVE AGONISTS OF THE ESTROGEN RECEPTOR BETA ISOFORM
  [FR] COMPOSÉS SUBSTITUÉS DE (4'-HYDROXYPHENYL)CYCLOALKANE ET LEURS UTILISATIONS EN TANT QU'AGONISTES SÉLECTIFS DE L'ISOFORME BÊTA DU RÉCEPTEUR D'ŒSTROGÈNES

  摘要：

  本文披露了替代的(4'-羟基苯基)环烷化合物及其作为雌激素受体β异构体（ERβ）的选择性激动剂的用途。所披露的化合物可以制成药物组合物，并用于治疗与ERβ活性相关的疾病，如增生性疾病和紊乱以及精神疾病或紊乱。

  公开号：

  WO2015077611A1
• 作为产物：
  描述：

  乙烯 、 (8R,9S,13S,14S)-3-Benzyloxy-13-methyl-17-vinyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthrene 在 四氟硼酸-二乙醚络合物 、 Ru(CO)H(Cl)(tri(cyclohexyl)phosphine)₃ 作用下， 以 乙醚 、 苯 为溶剂， 反应 7.25h， 以88%的产率得到17-(1-methyl-2-propenyl)-3-(phenylmethoxy)-estra-1,3,5(10),16-tetraene
  参考文献：
  名称：

  Regio- and Stereoselective Ruthenium-Catalyzed Hydrovinylation of 1,3-Dienes:  Application to the Generation of a 20(S) Steroidal Side Chain

  摘要：

  The addition of ethylene to 1,3-dienes and 1-vinylcycloalkenes, catalyzed by two ruthenium complexes, proceeds in a regioselective fashion to afford 3-methyl-1,4-dienes as products. For a steroidal-based 1-vinylcycloalkene, the addition is stereospecific, giving a product with a 20(S) configuration.

  DOI：

  10.1021/ol030031+

文献信息

• Substituted (4'-hydroxyphenyl)cyclohexane compounds and uses thereof as selective agonists of the estrogen receptor beta isoform
  申请人：Marquette University

  公开号：US10570077B2

  公开（公告）日：2020-02-25

  Disclosed are substituted (4′-hydroxylphenyl)cycloalkane compounds and there use as selective agonists of the estrogen receptor beta isoform (ERβ). The disclosed compounds may be formulated as pharmaceutical compositions and administered to treat diseases associated with ER activity, such as proliferative diseases and disorders and/or psychiatric diseases or disorders.

  公开了取代的（4′-羟基苯基）环烷烃化合物及其作为雌激素受体β异构体（ERβ）选择性激动剂的用途。所公开的化合物可配制成药物组合物，用于治疗与ER活性相关的疾病，如增殖性疾病和紊乱和/或精神疾病或紊乱。
• Ligand Tuning in Asymmetric Hydrovinylation of 1,3-Dienes: A Stereoselective Route to Either Steroid-C₂₀ (<i>S</i>) or -C₂₀ (<i>R</i>) Derivatives
  作者：Biswajit Saha、Craig R. Smith、T. V. RajanBabu

  DOI：10.1021/ja711475f

  日期：2008.7.1

  1,3-Dienes derived from steroidal D-ring C(17)-ketones undergo Ni(II)-catalyzed hydrovinylation to give 1,2- or 1,4-addition of ethylene. Using finely tuned phosphoramidite ligands, it is possible to synthesize either the C(20) (R)- or (S)-derivatives without mutual contamination. The proportion of the 1,4-adduct, which is also formed stereoselectively, can be minimized by optimizing the reaction conditions. Because the two alkenes in the resultant dienes have differing steric demands for many potential reactions, and are ideally juxtaposed for further D-ring functionalization, these intermediates could be useful for the preparation of biologically important compounds such as vitamin D analogs and various antitumor steroidal glycosides.
• SUBSTITUTED (4'-HYDROXYPHENYL)CYCLOAKLKANE COMPOUNDS AND USES THEREOF AS SELECTIVE AGONISTS OF THE ESTROGEN RECEPTOR BETA ISOFORM
  申请人：Marquette University

  公开号：US20160340279A1

  公开（公告）日：2016-11-24

  Disclosed are substituted (4′-hydroxylphenyl)cycloalkane compounds and there use as selective agonists of the estrogen receptor beta isoform (ERβ). The disclosed compounds may be formulated as pharmaceutical compositions and administered to treat diseases associated with ER activity, such as proliferative diseases and disorders and/or psychiatric diseases or disorders.