2-(tert-butyldimethylsilanyloxy)-1-prop-2-ynylcyclopent-2-enecarboxylic acid ethyl ester | 1187777-40-7

• 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: 2-(tert-butyldimethylsilanyloxy)-1-prop-2-ynylcyclopent-2-enecarboxylic acid ethyl ester
• 英文别名: Ethyl 2-[tert-butyl(dimethyl)silyl]oxy-1-prop-2-ynylcyclopent-2-ene-1-carboxylate
• CAS: 1187777-40-7
• 化学式: C₁₇H₂₈O₃Si
• 分子量: 308.493
• InChiKey: MQXBCBSERMJHAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.26
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(tert-butyldimethylsilanyloxy)-1-prop-2-ynylcyclopent-2-enecarboxylic acid ethyl 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， 反应 12.0h， 以85%的产率得到8-oxo-bicyclo[3.2.1]oct-3-ene-1-carboxylic acid ethyl 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：

  叔丁基二甲硅基三氟甲磺酸酯 、 2-(ethoxycarbonyl)-2-propargylcyclopentanone 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以86%的产率得到2-(tert-butyldimethylsilanyloxy)-1-prop-2-ynylcyclopent-2-enecarboxylic acid ethyl 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