(E)-1-nitro-1-tetradecene

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (E)-1-nitro-1-tetradecene
• 英文别名: 1-Nitrotetradec-1-ene；(E)-1-nitrotetradec-1-ene
• 化学式: C₁₄H₂₇NO₂
• 分子量: 241.374
• InChiKey: JXKYYLLCYKPPNX-BUHFOSPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  17
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  1-十四烯 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 dipotassium peroxodisulfate 、 sodium nitrite 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以57%的产率得到(E)-1-nitro-1-tetradecene
  参考文献：
  名称：

  K 2 S 2 O 8 -mediated nitration of alkenes with NaNO 2 and 2,2,6,6-tetramethylpiperidine-1-oxyl: stereoselective synthesis of ( E )-nitroalkenes

  摘要：

  A transition-metal-free nitration of alkenes with NaNO2 in the presence of K2S2O8 and 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) is developed. The transformation exhibits a broad substrate scope and good functional group tolerance, thus providing a new and expedient protocol for stereoselective synthesis of (E)-nitroalkenes with moderate to good yields. Moreover, the nitration processes of (E)- and (Z)-stilbene are also studied: even though the proportion of substrates is different, the E/Z ratio of the products is basically the same. Based upon experimental observations, a possible reaction mechanism is proposed. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.11.064

文献信息

• K 2 S 2 O 8 -mediated nitration of alkenes with NaNO 2 and 2,2,6,6-tetramethylpiperidine-1-oxyl: stereoselective synthesis of ( E )-nitroalkenes
  作者：An Zhao、Qing Jiang、Jing Jia、Bin Xu、Yufeng Liu、Mingzhong Zhang、Qiang Liu、Weiping Luo、Cancheng Guo

  DOI：10.1016/j.tetlet.2015.11.064

  日期：2016.1

  A transition-metal-free nitration of alkenes with NaNO2 in the presence of K2S2O8 and 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) is developed. The transformation exhibits a broad substrate scope and good functional group tolerance, thus providing a new and expedient protocol for stereoselective synthesis of (E)-nitroalkenes with moderate to good yields. Moreover, the nitration processes of (E)- and (Z)-stilbene are also studied: even though the proportion of substrates is different, the E/Z ratio of the products is basically the same. Based upon experimental observations, a possible reaction mechanism is proposed. (C) 2015 Elsevier Ltd. All rights reserved.