(16α,17β)-3-(benzyloxy)-17-methylgona-1,3,5(10),13-tetraen-16-ol | 1314110-76-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: (16α,17β)-3-(benzyloxy)-17-methylgona-1,3,5(10),13-tetraen-16-ol
• 英文别名: (8R,9S,16R,17R)-17-methyl-3-phenylmethoxy-7,8,9,11,12,15,16,17-octahydro-6H-cyclopenta[a]phenanthren-16-ol
• CAS: 1314110-76-3
• 化学式: C₂₅H₂₈O₂
• 分子量: 360.496
• InChiKey: LDTSRXCFWRUBFA-KHRGITBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  (16α,17β)-3-(benzyloxy)-17-methylgona-1,3,5(10),13-tetraen-16-ol 在 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate 作用下， 反应 30.0h， 以75%的产率得到3-(benzyloxy)-17-methylgona-1,3,5(10),8,11,13-hexaene
  参考文献：
  名称：

  Ionic Liquid-Promoted Wagner–Meerwein Rearrangement of 16α,17α-Epoxyandrostanes and 16α,17α-Epoxyestranes

  摘要：

  Ionic liquids 1-butyl-3-methylimidazolium hexafluorophosphate ([bmitn](+)[PF(6)](-)) and 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim](-)(+)[BF(4)](-)) were found to promote an unusual Wagner-Meerwein rearrangement of steroidal 16 alpha,17 alpha-epolddes leading to unnatural 13-epi-18-nor-16-one derivatives as the main products. These compounds were isolated in good to excellent yields. 16 alpha-Hydroxy-Delta(13)-18-norsteroid5, the results of the usual rearrangement, were obtained as minor components of the reaction mixtures. The ionic liquid [bmim](+)[PF(6)](-) was shown to induce C-ring aromatization of 16 alpha,17 alpha-epoxyestranes due to the formation of HF, the hydrolysis product of [PF(6)](-). Increasing amounts of HF and [PO(2)F(2)](-) were detected by (19)F and (31)P NMR when the ionic liquid was reused. The structures of the steroidal products, 16-oxo-18-nor-13 alpha-steroid derivatives, 16 alpha-hydroxy-Delta(13)-18-norsteroids, and C-aromatic compounds were determined by two-dimensional NMR techniques and high-resolution mass spectrometry (HRMS). The ionic liquids were recirculated efficiently.

  DOI：

  10.1021/jo2006285
• 作为产物：
  描述：

  在 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate 作用下， 反应 30.0h， 以73%的产率得到(13α,17α)-3-(benzyloxy)-17-methylgona-1,3,5(10)-trien-16-one
  参考文献：
  名称：

  Ionic Liquid-Promoted Wagner–Meerwein Rearrangement of 16α,17α-Epoxyandrostanes and 16α,17α-Epoxyestranes

  摘要：

  Ionic liquids 1-butyl-3-methylimidazolium hexafluorophosphate ([bmitn](+)[PF(6)](-)) and 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim](-)(+)[BF(4)](-)) were found to promote an unusual Wagner-Meerwein rearrangement of steroidal 16 alpha,17 alpha-epolddes leading to unnatural 13-epi-18-nor-16-one derivatives as the main products. These compounds were isolated in good to excellent yields. 16 alpha-Hydroxy-Delta(13)-18-norsteroid5, the results of the usual rearrangement, were obtained as minor components of the reaction mixtures. The ionic liquid [bmim](+)[PF(6)](-) was shown to induce C-ring aromatization of 16 alpha,17 alpha-epoxyestranes due to the formation of HF, the hydrolysis product of [PF(6)](-). Increasing amounts of HF and [PO(2)F(2)](-) were detected by (19)F and (31)P NMR when the ionic liquid was reused. The structures of the steroidal products, 16-oxo-18-nor-13 alpha-steroid derivatives, 16 alpha-hydroxy-Delta(13)-18-norsteroids, and C-aromatic compounds were determined by two-dimensional NMR techniques and high-resolution mass spectrometry (HRMS). The ionic liquids were recirculated efficiently.

  DOI：

  10.1021/jo2006285