(8R,9S,13S,14S,16S,17R)-3-Methoxy-13-methyl-16-[(E)-3-phenyl-prop-2-en-(E)-ylideneamino]-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-ol | 250713-46-3

• 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,16S,17R)-3-Methoxy-13-methyl-16-[(E)-3-phenyl-prop-2-en-(E)-ylideneamino]-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-ol
• CAS: 250713-46-3
• 化学式: C₂₈H₃₃NO₂
• 分子量: 415.576
• InChiKey: XGQHFSITZOUMDW-KBKOPDLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.67
• 重原子数：
  31.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  41.82
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 (8R,9S,13S,14S,16S,17R)-3-Methoxy-13-methyl-16-[(E)-3-phenyl-prop-2-en-(E)-ylideneamino]-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-ol 在 palladium diacetate 、 水 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 trans-2-phenylcyclopropanecarbaldehyde
  参考文献：
  名称：

  O-Silylated steroidal cis-aminoalcohols as chiral auxiliaries: highly diastereoselective Pd-catalyzed cyclopropanation of α,β-unsaturated aldimines

  摘要：

  alpha,beta-Unsaturated imines, obtained from cis-17-silyloxy-16-amino steroids and alpha,beta-unsaturated aldehydes, react with diazomethane in the presence of a catalytic amount of Pd(OAc)(2) with high chemo- and diastereoselectivities to form steroidal cyclopropanocarbaldimines, chromatography on silica gel gives the substituted cyclopropanocarbaldehydes with a high enantiomeric excess and allows recovery of the chiral steroidal auxiliaries. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00334-9
• 作为产物：
  描述：

  反式肉桂醛 、 16β-amino-17β-hydroxy-3-methoxy-estra-1,3,5(10)-triene 以 甲醇 为溶剂， 反应 4.0h， 以87.5%的产率得到(8R,9S,13S,14S,16S,17R)-3-Methoxy-13-methyl-16-[(E)-3-phenyl-prop-2-en-(E)-ylideneamino]-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-ol
  参考文献：
  名称：

  Steroid imines as chiral ligands. Diastereoselective formation of (1-azadiene)Fe(CO)3 complexes by sterically tuning the ligand coordination spheres

  摘要：

  The condensation of steroid amines with alpha,beta-unsaturated aldehydes leads to the formation of chiral 1-azadiene ligands with a steroid core attached to nitrogen. If the azadiene chain is situated at the D-ring of the steroid at C-16 or C-17, respectively, the two diastereotopic faces of the ligand may be discriminated by different neighbouring substituents and their configuration. The reaction of these ligands with Fe-2(CO)(9) produces mixtures of diastereomeric (1-azadiene)Fe(CO)(3) complexes. By increasing the steric demands of the neighbouring groups it is possible to improve the diastereoselectivity of this complexation reaction from 1:1 mixtures using the least sterically hindered ligands to complete diastereoselectivity using the azadiene derived from cinnamaldehyde and 16 beta-amino-3-methoxy-estra-1,3,5(10)-triene-17 beta-ol. In addition, the molecular structure of [17 beta-(3-phenyl-prop-2-enyliden)-amino-3-methoxy-estra-1,3,5(10)-triene]Fe(CO)(3) was determined by X-ray structure analysis. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00281-5