1-(3-bromoprop-2-ynyl)-3-methyl-2-triethylsilanyloxycyclohex-2-enecarboxylic acid methyl ester | 1187777-65-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1-(3-bromoprop-2-ynyl)-3-methyl-2-triethylsilanyloxycyclohex-2-enecarboxylic acid methyl ester
• CAS: 1187777-65-6
• 化学式: C₁₈H₂₉BrO₃Si
• 分子量: 401.416
• InChiKey: NPYNRKKRZUGERO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.37
• 重原子数：
  23.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(3-bromoprop-2-ynyl)-3-methyl-2-triethylsilanyloxycyclohex-2-enecarboxylic acid methyl ester 在 (乙腈)[(2-联苯)二叔丁基膦]六氟锑酸金(I) 作用下， 以 丙酮 为溶剂， 以93%的产率得到4-bromo-5-methyl-9-oxobicyclo[3.3.1]non-3-ene-1-carboxylic acid methyl ester
  参考文献：
  名称：

  Gold-Catalyzed Synthesis of Carbon-Bridged Medium-Sized Rings

  摘要：

  Bicyclo[m.n.1]alkenone frameworks possessing quaternary carbon centers adjacent to a bridged ketone are frequently found in bioactive natural products. Although several methods have been developed to construct such frameworks, most of them are specific to a particular scaffold. Herein, we report a mild and highly efficient method to generate carbon-bridged frameworks of various sizes using phosphino gold(I) catalysts.

  DOI：

  10.1021/ol901722q
• 作为产物：
  描述：

  3-methyl-1-prop-2-ynyl-2-triethylsilanyloxy-cyclohex-2-enecarboxylic acid methyl ester 在 N-溴代丁二酰亚胺(NBS) 、 silver nitrate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以85%的产率得到1-(3-bromoprop-2-ynyl)-3-methyl-2-triethylsilanyloxycyclohex-2-enecarboxylic acid methyl ester
  参考文献：
  名称：

  Gold-Catalyzed Synthesis of Carbon-Bridged Medium-Sized Rings

  摘要：

  Bicyclo[m.n.1]alkenone frameworks possessing quaternary carbon centers adjacent to a bridged ketone are frequently found in bioactive natural products. Although several methods have been developed to construct such frameworks, most of them are specific to a particular scaffold. Herein, we report a mild and highly efficient method to generate carbon-bridged frameworks of various sizes using phosphino gold(I) catalysts.

  DOI：

  10.1021/ol901722q