3-methoxy-estra-1,3,5(10)-triene-17-keto-16-oxime | 40822-17-1

• 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: 3-methoxy-estra-1,3,5(10)-triene-17-keto-16-oxime
• 英文别名: 3-methoxy-16-oximino-1,3,5(10)-estratrien-17-one；3-methoxy-1,3,5(10)-triene-16,17-dione 16-oxime；3-Methoxyestra-1,3,5(10)-triene-16,17-dione 16-oxime；(8R,9S,13S,14S,16E)-16-hydroxyimino-3-methoxy-13-methyl-6,7,8,9,11,12,14,15-octahydrocyclopenta[a]phenanthren-17-one
• CAS: 40822-17-1
• 化学式: C₁₉H₂₃NO₃
• 分子量: 313.397
• InChiKey: CZHINTJOYWQKED-JQQXAHOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  58.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-methoxy-estra-1,3,5(10)-triene-17-keto-16-oxime 在 乙酸酐 作用下， 以 溶剂黄146 为溶剂， 反应 20.0h， 以50%的产率得到3-methoxy-17-aza-D-homo-1,3,5(10)-estratriene-16,17a-dione
  参考文献：
  名称：

  Gupta, Ranju; Jindal, Dharam Paul; Borras, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 5, p. 563 - 571

  摘要：

  DOI：

文献信息

• A novel fragmentation-cyclization reaction of steroidal α-hydroxy oximes
  作者：Katarina Penov-Gaši、Dušan Miljković、Ljubica Medić-Mijačević、Evgenija Durendić、Julijana Petrović、Vjera Pejanović、Slobodanka Stanković、Dušan Lazar

  DOI：10.1016/s0040-4039(98)02166-2

  日期：1998.12

  By a novel “one pot” fragmentation-cyclization reaction 17β-hydroxy-17α-substituted-16-oximino derivatives in the androstane and estrane series were converted to a new type of D-homo derivative.

  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。
• 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。
• 17α-Benzyl-17β-hydroxy-16-hydroxyimino-3-methoxyestra-1,3,5(10)-triene
  作者：S. Stankovic、D. Lazar、D. Miljkovic、L. Medic-Mijacevic、K. Gasi、R. Kovacevic、C. Courseille

  DOI：10.1107/s0108270195011309

  日期：1996.8.15

  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.
• <scp>D</scp>-Secoestrone derivatives. V
  作者：Dušan Lazar、Slobodanka Stanković、Vjera Pejanović、Christiane Courseille

  DOI：10.1107/s0108270101018182

  日期：2002.2.15

  The two title 16,17-secoestrone derivatives, 3-methoxy-17-oxo-17-phenyl-16,17-secoestra-1,3,5(10)-triene-16-nitrile, C25H27NO2, (I) (17-oxo substituent), and 17-hydroxy-3-methoxy-17-phenyl-16,17-secoestra-1,3,5(10)-triene-16-nitrile, C25H29NO2, (II) (17-hydroxy substituent), have quite different conformations in the solid state. These conformational differences can be minimized by molecular mechanics calculations. Thus, the remarkable difference in the biological activity of the two compounds, e.g. the strong oestrogenic characteristics of (I) and the moderate antioestrogenic action of (II), must be caused by the difference in substitution at C17. In (II), the molecules are linked by O-H...N hydrogen bonds, forming spirals along the b direction.
• Gupta, Ranju; Jindal, Dharam Paul; Borras, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 5, p. 563 - 571
  作者：Gupta, Ranju、Jindal, Dharam Paul、Borras、Legros、Leclercq

  DOI：——

  日期：——