(8R,9S,13S,14S,16S,17R)-17-(tert-Butyl-diphenyl-silanyloxy)-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-16-ylamine | 443889-50-7

• 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: (8R,9S,13S,14S,16S,17R)-17-(tert-Butyl-diphenyl-silanyloxy)-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-16-ylamine
• 英文别名: (8R,9S,13S,14S,16S,17R)-17-[tert-butyl(diphenyl)silyl]oxy-3-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-16-amine
• CAS: 443889-50-7
• 化学式: C₃₅H₄₅NO₂Si
• 分子量: 539.833
• InChiKey: CBCLSPUEVYIYJL-PYDWYRNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.43
• 重原子数：
  39
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (8R,9S,13S,14S,16S,17R)-17-(tert-Butyl-diphenyl-silanyloxy)-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-16-ylamine 在 palladium diacetate 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 23.0h， 生成 [(8R,9S,13S,14S,16S,17R)-17-(tert-Butyl-diphenyl-silanyloxy)-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-16-yl]-[1-((1S,2S)-2-phenyl-cyclopropyl)-meth-(E)-ylidene]-amine
  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：

  16β-amino-17β-hydroxy-3-methoxy-estra-1,3,5(10)-triene 、 叔丁基二苯基氯硅烷 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 96.0h， 生成 (8R,9S,13S,14S,16S,17R)-17-(tert-Butyl-diphenyl-silanyloxy)-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-16-ylamine
  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

文献信息

• O-Silylated steroidal cis-aminoalcohols as chiral auxiliaries: highly diastereoselective Pd-catalyzed cyclopropanation of α,β-unsaturated aldimines
  作者：M. Dubs、H. Dieks、W. Günther、M. Kötteritzsch、W. Poppitz、B. Schönecker

  DOI：10.1016/s0040-4039(02)00334-9

  日期：2002.4

  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.