(E)-allyl 11-nitroundec-10-enoate | 1423157-14-5

• 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)-allyl 11-nitroundec-10-enoate
• 英文别名: prop-2-enyl (E)-11-nitroundec-10-enoate
• CAS: 1423157-14-5
• 化学式: C₁₄H₂₃NO₄
• 分子量: 269.341
• InChiKey: CLBPESYRAIZMBC-ZRDIBKRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  12
• 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-enyl 10-oxodecanoate 在 亚硝酸特丁酯 、 2,2,6,6-四甲基哌啶氧化物 、 potassium tert-butylate 作用下， 以 1,4-二氧六环 、 苯 为溶剂， 反应 12.0h， 生成 (E)-allyl 11-nitroundec-10-enoate
  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

• Efficient and Stereoselective Nitration of Mono- and Disubstituted Olefins with AgNO₂ and TEMPO
  作者：Soham Maity、Srimanta Manna、Sujoy Rana、Togati Naveen、Arijit Mallick、Debabrata Maiti

  DOI：10.1021/ja311942e

  日期：2013.3.6

  common and versatile reagent. Its synthesis from olefin is generally limited by the formation of mixture of cis and trans compounds. Here we report that silver nitrite (AgNO2) along with TEMPO can promote the regio- and stereoselective nitration of a broad range of olefins. This work discloses a new and efficient approach wherein starting from olefin, nitroalkane radical formation and subsequent transformations

  硝基烯烃是一种常见且用途广泛的试剂。它从烯烃合成通常受到顺式和反式化合物混合物的形成的限制。在这里，我们报告亚硝酸银 (AgNO2) 与 TEMPO 一起可以促进范围广泛的烯烃的区域和立体选择性硝化。这项工作公开了一种新的有效方法，其中从烯烃开始，硝基烷烃自由基形成和随后的转化以立体选择性方式导致所需的硝基烯烃。
• A Predictably Selective Nitration of Olefin with Fe(NO₃)₃ and TEMPO
  作者：Togati Naveen、Soham Maity、Upendra Sharma、Debabrata Maiti

  DOI：10.1021/jo400598p

  日期：2013.6.21

  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.