3-[5-[Tert-butyl(dimethyl)silyl]oxy-2-chlorophenyl]propan-1-ol | 181648-41-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-[5-[Tert-butyl(dimethyl)silyl]oxy-2-chlorophenyl]propan-1-ol
• CAS: 181648-41-9
• 化学式: C₁₅H₂₅ClO₂Si
• 分子量: 300.901
• InChiKey: RRYPOCWWIMBGDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.65
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  3-[5-[Tert-butyl(dimethyl)silyl]oxy-2-chlorophenyl]propan-1-ol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到3-[5-[Tert-butyl(dimethyl)silyl]oxy-2-chlorophenyl]propanal
  参考文献：
  名称：

  Synthesis of an Azasteroid Using an Acyl Iminium Ion-Initiated Tandem Cyclization

  摘要：

  An acyl iminium ion-initiated tandem cyclization gave an unexpected dienone product, a secoazasteroid (2). The factors governing the formation of 2 were investigated in an attempt to optimize its formation. The reaction was applied to a more elaborate system, resulting in the synthesis of the full steroid skeleton of 13-azaandrosta-1,4-diene-3,17-dione (8), which contains the unusual substitution of a chlorine atom for the axial 19-methyl.

  DOI：

  10.1021/jo960673t
• 作为产物：
  描述：

  4-氯-3-甲基苯酚 在 咪唑 、 N-溴代丁二酰亚胺(NBS) 、 lithium aluminium tetrahydride 、 过氧化氢苯甲酰 、 lithium diisopropyl amide 作用下， 以 四氯化碳 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.67h， 生成 3-[5-[Tert-butyl(dimethyl)silyl]oxy-2-chlorophenyl]propan-1-ol
  参考文献：
  名称：

  Synthesis of an Azasteroid Using an Acyl Iminium Ion-Initiated Tandem Cyclization

  摘要：

  An acyl iminium ion-initiated tandem cyclization gave an unexpected dienone product, a secoazasteroid (2). The factors governing the formation of 2 were investigated in an attempt to optimize its formation. The reaction was applied to a more elaborate system, resulting in the synthesis of the full steroid skeleton of 13-azaandrosta-1,4-diene-3,17-dione (8), which contains the unusual substitution of a chlorine atom for the axial 19-methyl.

  DOI：

  10.1021/jo960673t

文献信息

• Synthesis of an Azasteroid Using an Acyl Iminium Ion-Initiated Tandem Cyclization
  作者：Arthur G. Romero、Jeffrey A. Leiby、Stephen A. Mizsak

  DOI：10.1021/jo960673t

  日期：1996.1.1

  An acyl iminium ion-initiated tandem cyclization gave an unexpected dienone product, a secoazasteroid (2). The factors governing the formation of 2 were investigated in an attempt to optimize its formation. The reaction was applied to a more elaborate system, resulting in the synthesis of the full steroid skeleton of 13-azaandrosta-1,4-diene-3,17-dione (8), which contains the unusual substitution of a chlorine atom for the axial 19-methyl.