2-hydroxy-3-[1-(2-furanyl)-2-nitroethyl]-1,4-naphthoquinone | 1187616-56-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-hydroxy-3-[1-(2-furanyl)-2-nitroethyl]-1,4-naphthoquinone
• 英文别名: 2-(1-(furan-2-yl)-2-nitroethyl)-3-hydroxynaphthalene-1,4-dione
• CAS: 1187616-56-3
• 化学式: C₁₆H₁₁NO₆
• 分子量: 313.266
• InChiKey: XOFNDGKRIZJKHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.53
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  110.65
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  1-(2-糠酰)-2-硝基乙烯 、 2-羟基-1,4-萘醌 以 水 为溶剂， 反应 18.0h， 以88%的产率得到2-hydroxy-3-[1-(2-furanyl)-2-nitroethyl]-1,4-naphthoquinone
  参考文献：
  名称：

  Facile and highly efficient method for the C-alkylation of 2-hydroxy-1,4-naphthoquinone to nitroalkenes under catalyst-free ‘on water’ conditions

  摘要：

  C-Alkylation of 2-hydroxy-1,4-naphthoquinone to various nitroolefins was achieved under catalyst-free employing 'on water' conditions. The mechanism for the formation can be explained oil the basis of dual activation of nitroalkene and 2-hydroxy-1,4-naphthoquinones via hydrogen bonding. Simple reaction conditions, high yields of the products, and environmentally benign medium are attractive features of this method. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.06.107

文献信息

• Organocatalytic Highly Enantioselective Michael Addition of 2-Hydroxy-1,4-naphthoquinones to Nitroalkenes
  作者：Wen-Ming Zhou、Han Liu、Da-Ming Du

  DOI：10.1021/ol800945e

  日期：2008.7.3

  The first organocatalytic enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinones to nitroalkenes for the direct synthesis of chiral nitroalkylated naphthoquinone derivatives was investigated. Good yields and excellent enantioselectivities (up to >99% ee) could be achieved. This organocatalytic asymmetric Michael addition provides an efficient route toward the synthesis of optically active

  为了直接合成手性硝基烷基化萘醌衍生物，研究了2-羟基-1,4-萘醌向硝基烯烃的首次有机催化对映选择性迈克尔加成反应。可以获得良好的产率和优异的对映选择性（高达> 99％ee）。这种有机催化的不对称迈克尔加成提供了合成光学活性官能化萘醌的有效途径。