(2R,3R,E)-1-(4-(tert-butoxy)phenyl)-2-((tert-butoxycarbonyl)(methyl)amino)dodec-6-en-3-yl acetate | 1292308-73-6

• 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: (2R,3R,E)-1-(4-(tert-butoxy)phenyl)-2-((tert-butoxycarbonyl)(methyl)amino)dodec-6-en-3-yl acetate
• CAS: 1292308-73-6
• 化学式: C₃₀H₄₉NO₅
• 分子量: 503.723
• InChiKey: QCGJBLRPXYYIJY-FDFRSNTISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.49
• 重原子数：
  36.0
• 可旋转键数：
  13.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  65.07
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,E)-1-(4-(tert-butoxy)phenyl)-2-((tert-butoxycarbonyl)(methyl)amino)dodec-6-en-3-yl acetate 在 二异丁基氢化铝 、 rochelle salt 作用下， 以 二氯甲烷 为溶剂， 反应 1.75h， 以98%的产率得到tert-butyl ((2R,3R,E)-1-(4-(tert-butoxy)phenyl)-3-hydroxydodec-6-en-2-yl)(methyl)carbamate
  参考文献：
  名称：

  Unexpected stereochemical tolerance for the biological activity of tyroscherin

  摘要：

  Here we describe the concise syntheses of the 15 diastereomers and key analogs of the natural product tyroscherin. While systematic analysis of the analogs clearly demonstrated that the hydrocarbon tail is important for biological activity, structure-activity relationship studies of the complete tyroscherin diastereoarray revealed a surprisingly expansive stereochemical tolerance for the cytotoxic activity. Our results represent a departure from the tenet that biological activity is constrained to a narrow pharmacophore, and highlight the recently emerging appreciation for stereochemical flexibility in defining the essential structural elements of biologically active small molecules. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.01.027
• 作为产物：
  描述：

  tert-butyl (2R,3R)-1-(4-tert-butoxyphenyl)-3-hydroxyhept-6-en-2-yl(methyl)carbamate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 生成 (2R,3R,E)-1-(4-(tert-butoxy)phenyl)-2-((tert-butoxycarbonyl)(methyl)amino)dodec-6-en-3-yl acetate
  参考文献：
  名称：

  Unexpected stereochemical tolerance for the biological activity of tyroscherin

  摘要：

  Here we describe the concise syntheses of the 15 diastereomers and key analogs of the natural product tyroscherin. While systematic analysis of the analogs clearly demonstrated that the hydrocarbon tail is important for biological activity, structure-activity relationship studies of the complete tyroscherin diastereoarray revealed a surprisingly expansive stereochemical tolerance for the cytotoxic activity. Our results represent a departure from the tenet that biological activity is constrained to a narrow pharmacophore, and highlight the recently emerging appreciation for stereochemical flexibility in defining the essential structural elements of biologically active small molecules. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.01.027