16-oximino-17α-benzyl-17β-hydroxy-16-hydroxyimino-3-methoxyestra-1,3,5(10)-triene | 182161-85-9

• 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
• 英文名称: 16-oximino-17α-benzyl-17β-hydroxy-16-hydroxyimino-3-methoxyestra-1,3,5(10)-triene
• 英文别名: (8R,9S,13S,14S,16E,17R)-17-benzyl-16-hydroxyimino-3-methoxy-13-methyl-6,7,8,9,11,12,14,15-octahydrocyclopenta[a]phenanthren-17-ol
• CAS: 182161-85-9
• 化学式: C₂₆H₃₁NO₃
• 分子量: 405.537
• InChiKey: VOOVKZQCWNIZGI-CCNORUBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  62
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  16-oximino-17α-benzyl-17β-hydroxy-16-hydroxyimino-3-methoxyestra-1,3,5(10)-triene 在 氢氧化钾 作用下， 以 乙二醇 为溶剂， 以84%的产率得到(4aS,4bR,10bS,12aS)-3-amino-8-methoxy-12a-methyl-2-phenyl-4,4a,4b,5,6,10b,11,12-octahydrochrysen-1-one
  参考文献：
  名称：

  甾族α-羟基肟的新型断裂环化反应

  摘要：

  通过新颖的“一锅”裂解-环化反应，雄甾烷和雌激素系列中的17β-羟基-17α-取代的16-肟基衍生物被转化为新型的D-homo衍生物。

  DOI：

  10.1016/s0040-4039(98)02166-2
• 作为产物：
  描述：

  benzyllithium 、 3-methoxy-estra-1,3,5(10)-triene-17-keto-16-oxime 以 四氢呋喃 为溶剂， 以68%的产率得到16-oximino-17α-benzyl-17β-hydroxy-16-hydroxyimino-3-methoxyestra-1,3,5(10)-triene
  参考文献：
  名称：

  17α-Benzyl-17β-hydroxy-16-hydroxyimino-3-methoxyestra-1,3,5(10)-triene

  摘要：

  The asymmetric unit of the title compound, 17 alpha-benzyl- 16-hydroxyimino-3-methoxyestra-1,3,5(10)-trien-17 beta-ol, C26H31NO3, contains two molecules which differ in the orientations of the methoxy groups at C(3). The 17-hydroxy and 16-hydroxyimino moieties are involved in intramolecular N ... O and intermolecular N ... O and O ... O hydrogen bonds. The hydrogen-bond network accounts for the differences in bond and torsion angles of the alpha-hydroxyimino moieties of the symmetry-independent molecules. This has been confirmed by molecular-mechanics calculations on the individual molecules which indicate that they have the same geometry in their energy minimum states.

  DOI：

  10.1107/s0108270195011309

文献信息

• A novel rearrangement of steroidal α-hydroxy oximes
  作者：Dušan Miljković、Katarina Penov-Gaši、Evgenija Djurendić、Marija Sakač、Ljubica Medić-Mijačević、Vjera Pejanović、Slobodanka Stanković、Dušan Lazar

  DOI：10.1016/s0040-4039(97)00996-9

  日期：1997.6

  16-oximino-17α-benzyl-17β-hydroxy derivatives in the androstane and estrane series the 16-oxo-17β-benzyl-17α-hydroxy derivatives 6 and 7 with inversed configuration at C17 were obtained. A mechanism for this novel rearrangement is proposed.

  通过酸性三氯化钛对雄甾烷和雌激素系列中的16-氧亚氨基-17α-苄基-17β-羟基衍生物的作用，得到在C 17处具有反向构型的16-氧代-17β-苄基-17α-羟基衍生物6和7。。提出了用于这种新颖的重排的机制。
• <scp>D</scp>-Secoestrone derivatives. VI. 17β-Benzyl-17α-hydroxy-3-methoxyestra-1,3,5(10)-trien-16-one
  作者：Slobodanka Stanković、Dušan Lazar、Ljubica Medić-Mijačević、Katarina Penov-Gaši、Marija Sakač、Silvana Andrić、Bruvo Milenko

  DOI：10.1107/s0108270101020807

  日期：2002.3.15

  The title molecule, C(26)H(30)O(3), shows a novel chemical rearrangement of the substituents at position 17, i.e. an alpha-orientation of the hydroxy group and a beta-orientation of the bulky benzyl moiety. The packing arrangement consists of coils formed by O(2)...O(3) hydrogen bonds along the c axis. The compound shows complete loss of oestrogenic activity, and neither does it exhibit an antagonistic

  标题分子C（26）H（30）O（3）显示出位置17处取代基的新型化学重排，即羟基的α-方向和大体积苄基部分的β-方向。填料排列由沿c轴由O（2）... O（3）氢键形成的线圈组成。该化合物显示出完全的雌激素活性丧失，也没有显示出拮抗作用。