(E)-prop-2-yn-1-yl 11-nitroundec-10-enoate | 1440549-02-9

• 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: (E)-prop-2-yn-1-yl 11-nitroundec-10-enoate
• 英文别名: prop-2-ynyl (E)-11-nitroundec-10-enoate
• CAS: 1440549-02-9
• 化学式: C₁₄H₂₁NO₄
• 分子量: 267.325
• InChiKey: ZJNJAIVIRWPPIZ-ZRDIBKRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  prop-2-yn-1-yl undec-10-enoate 在 Iron(III) nitrate nonahydrate 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 以58%的产率得到(E)-prop-2-yn-1-yl 11-nitroundec-10-enoate
  参考文献：
  名称：

  A Predictably Selective Nitration of Olefin with Fe(NO₃)₃ and TEMPO

  摘要：

  Ferric nitrate with catalytic TEMPO has been identified as a useful reagent for regio- and stereoselective nitration of a wide variety of aromatic, aliphatic, and heteroaromatic olefins. This reaction provided nitroolefins in preparatively useful yields with excellent E-selectivity. Due to its mild nature and operational simplicity, the present protocol is expected to find application in synthetic setup.

  DOI：

  10.1021/jo400598p

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.