(2E)-5-methyl-2-nitrohex-2-en-1-ol | 1175712-43-2

• 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: (2E)-5-methyl-2-nitrohex-2-en-1-ol
• CAS: 1175712-43-2
• 化学式: C₇H₁₃NO₃
• 分子量: 159.185
• InChiKey: JSQRLIMJGTUMAR-QPJJXVBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.19
• 重原子数：
  11.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  63.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2E)-5-methyl-2-nitrohex-2-en-1-ol 、 ethyl N-{[(4-nitrobenzene)sulfonyl]oxy}carbamate 在 calcium oxide 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以96%的产率得到ethyl 2-(hydroxymethyl)-3-(2-methylpropyl)-2-nitroaziridine-1-carboxylate
  参考文献：
  名称：

  Selective Amination Reactions of α-Nitro Aryl and Heteroaryl Enoates

  摘要：

  Highly functionalized tetrasubstituted alkenes were obtained by an unexpected amination reaction promoted by ethyl nosyloxycarbamate on various alpha-nitro aryl and heteroaryl enoates. A nitrene is likely the aminating species responsible for the observed insertion reaction leading to (E)-beta-amino alpha-nitro enoates as the major products, regardless of the substrate configuration. The compounds, bearing two nitrogenous functional groups in different oxidation states, can be regarded as interesting synthons. In contrast, aziridination was observed for alpha-nitro alkyl enoates or beta-nitro allylic alcohols.

  DOI：

  10.1021/jo4012859
• 作为产物：
  描述：

  2-硝基乙醇 、 异戊醛 在 哌啶 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以89%的产率得到(2E)-5-methyl-2-nitrohex-2-en-1-ol
  参考文献：
  名称：

  O-Arylsulfonyl hydroxylamines via a decarboxylative rearrangement

  摘要：

  (E)-O-aryl-sulfonyl-N-[2-nitroalk(-2-enyl)]hydroxyl-aamines were readily obtained with good yields starting from (E)-nitro-allyl-alcohols, the crucial step being an inorganic base-catalyzed de-carboxylative rearrangement of proposed labile unstable carbamates. A possible mechanism for the reaction, characterized by the unusual retention of the sulfonyl-oxy group, is proposed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.05.016