(S)-2-(1-(2-bromophenyl)-2-nitroethyl)-3-hydroxynaphthalene-1,4-dione | 1391940-89-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-2-(1-(2-bromophenyl)-2-nitroethyl)-3-hydroxynaphthalene-1,4-dione
• CAS: 1391940-89-8
• 化学式: C₁₈H₁₂BrNO₅
• 分子量: 402.201
• InChiKey: DUJZHHUNBWMHDU-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  97.51
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  2-羟基-1,4-萘醌 、 o-bromonitrostyrene 在 C₃₅H₄₆N₄O₁₀S 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以94%的产率得到(S)-2-(1-(2-bromophenyl)-2-nitroethyl)-3-hydroxynaphthalene-1,4-dione
  参考文献：
  名称：

  Sugar thiourea catalyzed highly enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinone to β-nitroalkenes

  摘要：

  利用一类新型糖-金鸡纳硫脲偶联物，实现了2-羟基-1,4-萘醌对β-硝基苯乙烯的高度对映选择性迈克尔加成反应。该方法具有显著优势，如催化剂用量低（1摩尔%）、高对映选择性（可达99% 对映体过量）、反应时间短和环境反应条件。

  DOI：

  10.1039/c2ra22270a

文献信息

• Threonine-derived thioureas as bifunctional organocatalysts for enantioselective Michael addition
  作者：Zhi Zheng、Jian Lin、Yang Sun、Suoqin Zhang

  DOI：10.1016/j.tetlet.2019.151382

  日期：2020.1

  A series of threonine-derived thioureas were developed through the facile modification of L-threonine chiral scaffold. The enantioselective efficiency were evaluated in the catalytic asymmetric Michael addition of 2-hydroxy-1,4-naphthoquinone to nitroalkenes, which afforded the chiral nitroalkylated naphthoquinone derivatives in high yields (up to 93%) and enantio-selectivities (up to 99% ee) under

  通过对L-苏氨酸手性骨架的轻松修饰，开发了一系列苏氨酸衍生的硫脲。通过将2-羟基-1,4-萘醌催化不对称迈克尔加成到硝基烯烃中来评估对映选择性效率，从而以高收率（高达93％）和对映选择性（高达99％ee）提供手性硝基烷基化萘醌衍生物。）在低催化剂负载量（3 mol％）下进行。
• BINOL–quinine–squaramides as efficient organocatalysts for the asymmetric Michael addition of 2-hydroxy-1,4-naphthoquinone to nitroalkenes
  作者：Enshan Zhou、Bin Liu、Chune Dong

  DOI：10.1016/j.tetasy.2013.11.019

  日期：2014.1

  A set of BINOL-quinine-squaramides were synthesized, and then used as organocatalysts to promote the catalytic enantioselective Michael addition reaction of 2-hydroxy-1,4-naphthoquinone to nitroalkenes with excellent yields and ees (up to 99% yield and 93% ee) at low catalyst loading (0.5 mol %). (C) 2013 Elsevier Ltd. All rights reserved.