(1S,4R,E)-2,2-dimethyl-3-(nitromethylene)bicyclo[2.2.1]heptane

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,4R,E)-2,2-dimethyl-3-(nitromethylene)bicyclo[2.2.1]heptane
• 英文别名: (1S,3E,4R)-2,2-dimethyl-3-(nitromethylidene)bicyclo[2.2.1]heptane
• 化学式: C₁₀H₁₅NO₂
• 分子量: 181.235
• InChiKey: YSRRDKSJZLZZDU-HWSTVNFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (-)-莰烯 在 亚硝酸特丁酯 、 2,2,6,6-四甲基哌啶氧化物 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以72%的产率得到(1S,4R,E)-2,2-dimethyl-3-(nitromethylene)bicyclo[2.2.1]heptane
  参考文献：
  名称：

  Stereoselective Nitration of Olefins with ^tBuONO and TEMPO: Direct Access to Nitroolefins under Metal-free Conditions

  摘要：

  Nitroolefins are essential elements for both synthetic chemistry and medicinal research. Despite significant improvements in nitration of olefin an efficient metal-free synthesis remains elusive so far. Herein, we disclose a new set of reagents to access nitroolefins in a single step under metal-free conditions. A wide range of olefins with diverse functionalities has been nitrated in synthetically useful yields. This transformation is operationally simple and exhibits excellent E-selectivity. Furthermore, site selective nitration in a complex setup makes this method advantageous.

  DOI：

  10.1021/ol401426p

文献信息

• Stereoselective Nitration of Olefins with ^<i>t</i>BuONO and TEMPO: Direct Access to Nitroolefins under Metal-free Conditions
  作者：Soham Maity、Togati Naveen、Upendra Sharma、Debabrata Maiti

  DOI：10.1021/ol401426p

  日期：2013.7.5

  Nitroolefins are essential elements for both synthetic chemistry and medicinal research. Despite significant improvements in nitration of olefin an efficient metal-free synthesis remains elusive so far. Herein, we disclose a new set of reagents to access nitroolefins in a single step under metal-free conditions. A wide range of olefins with diverse functionalities has been nitrated in synthetically useful yields. This transformation is operationally simple and exhibits excellent E-selectivity. Furthermore, site selective nitration in a complex setup makes this method advantageous.