[(8R,9S,13S,14S)-3-Allyloxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-(17E)-ylidene]-phenyl-amine | 474459-37-5

• 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: [(8R,9S,13S,14S)-3-Allyloxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-(17E)-ylidene]-phenyl-amine
• 英文别名: (8R,9S,13S,14S)-13-methyl-N-phenyl-3-prop-2-enoxy-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-imine
• CAS: 474459-37-5
• 化学式: C₂₇H₃₁NO
• 分子量: 385.549
• InChiKey: QTRXKAWPMUHYAX-QUUPDEESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [(8R,9S,13S,14S)-3-Allyloxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-(17E)-ylidene]-phenyl-amine 、 2-(氯甲基)喹啉 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.0h， 以48%的产率得到(3'R,8R,9S,13S,14S,17S)-13-methyl-1'-phenyl-3-prop-2-enoxy-3'-quinolin-2-ylspiro[7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-17,2'-aziridine]
  参考文献：
  名称：

  Chemoselective construction of novel steroid derivatives

  摘要：

  alpha-Halo-alpha-heteroarylalkyllithiums, generated by deprotonation of the corresponding halides, when added promptly to steroids with C=O or C=NR groups, lead to epoxides and aziridines. The reactions are regio- and stereoselective; in fact, in the presence of more than one C=O group, the oxido or aziridino functions are formed uniquely at the C=O of C-17 (or C-20 depending on its position in the starting molecule), and the C-20(R) stereoisomer is often the only product isolated. Protection of the hydroxyl group present on several considered steroids was required, and it was accomplished through derivatization in acetyl, ether, or lactone. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(02)00032-6
• 作为产物：
  描述：

  雌酚酮 在 sodium hydroxide 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 1.0h， 生成 [(8R,9S,13S,14S)-3-Allyloxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-(17E)-ylidene]-phenyl-amine
  参考文献：
  名称：

  Chemoselective construction of novel steroid derivatives

  摘要：

  alpha-Halo-alpha-heteroarylalkyllithiums, generated by deprotonation of the corresponding halides, when added promptly to steroids with C=O or C=NR groups, lead to epoxides and aziridines. The reactions are regio- and stereoselective; in fact, in the presence of more than one C=O group, the oxido or aziridino functions are formed uniquely at the C=O of C-17 (or C-20 depending on its position in the starting molecule), and the C-20(R) stereoisomer is often the only product isolated. Protection of the hydroxyl group present on several considered steroids was required, and it was accomplished through derivatization in acetyl, ether, or lactone. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(02)00032-6