17α-acetoxy-3-methoxyestra-1,3,5(10)-triene-17β-carbaldehyde | 129012-19-7

• 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: 17α-acetoxy-3-methoxyestra-1,3,5(10)-triene-17β-carbaldehyde
• 英文别名: 17β-Acetoxy-3-methoxyestra-1,3,5(10)-triene-17α-carbaldehyde；[(8R,9S,13S,14S,17S)-17-formyl-3-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl] acetate
• CAS: 129012-19-7
• 化学式: C₂₂H₂₈O₄
• 分子量: 356.462
• InChiKey: CIXBBEOJZZSDHG-LXHROKJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  17α-acetoxy-3-methoxyestra-1,3,5(10)-triene-17β-carbaldehyde 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 0.33h， 以88%的产率得到17α-Acetoxymethyl-3-methoxyestra-1,3,5(10)-trien-17β-ol
  参考文献：
  名称：

  Intramolecular condensation of steroidal 17α-formyl 17β-acetates: model studies on 19-norsteroids, and a route to 3-methoxy-19- nor-17α-pregna-1,3,5(10).Triene 21,17-carbolactone

  摘要：

  DOI：

  10.1016/s0040-4020(01)87846-7
• 作为产物：
  描述：

  3-甲氧基雌酮 在 对甲苯磺酸 potassium tert-butylate 作用下， 以 四氢呋喃 、 水 、 叔丁醇 、 苯 为溶剂， 反应 53.0h， 生成 17α-acetoxy-3-methoxyestra-1,3,5(10)-triene-17β-carbaldehyde
  参考文献：
  名称：

  Intramolecular condensation of steroidal 17α-formyl 17β-acetates: model studies on 19-norsteroids, and a route to 3-methoxy-19- nor-17α-pregna-1,3,5(10).Triene 21,17-carbolactone

  摘要：

  DOI：

  10.1016/s0040-4020(01)87846-7

文献信息

• Synthesis of .alpha.-hydroxy ketones by samarium(II) iodide-mediated coupling of organic halides, an isocyanide, and carbonyl compounds
  作者：Masahiro Murakami、Teiji Kawano、Hajime Ito、Yoshihiko Ito

  DOI：10.1021/jo00058a028

  日期：1993.3

  A new strategy for the synthesis of a-hydroxy ketones by samarium(II) iodide-mediated three-component coupling of organic halides, an isocyanide, and carbonyl compounds is disclosed. An (alpha-iminoalkyl)samarium(III) species is generated in situ by treatment of an organic halide with 2 equiv of samarium(II) iodide in the presence of 2,6-xylyl isocyanide. Subsequent treatment of the mixture with a carbonyl compound affords alpha-hydroxy imines, which are converted by acid-catalyzed hydrolysis to the corresponding alpha-hydroxy ketones. The mild reaction conditions employed are compatible with a variety of functionalities including terminal acetylenes and trimethylsilyl ethers. Application of the method to the synthesis of alpha-hydroxy aldehydes is also presented.
• Intramolecular condensation of steroidal 17α-formyl-17β-acetates
  作者：James R Bull、Lynne M Steer

  DOI：10.1016/s0040-4039(01)93385-4

  日期：1989.1