3-nitro-2-(4-bromophenyl)-2H-chromene | 1227402-09-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 3-nitro-2-(4-bromophenyl)-2H-chromene
• 英文别名: (R)-2-(4-bromophenyl)-3-nitro-2H-chromene；(2R)-2-(4-bromophenyl)-3-nitro-2H-chromene
• CAS: 1227402-09-6
• 化学式: C₁₅H₁₀BrNO₃
• 分子量: 332.153
• InChiKey: LZFDMLKMSPCJKO-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-bromo-β-nitrostyrene 、 salicyl N-tosylimine 在 N-[3,5-双(三氟甲基)苯基]-N'-[(8a,9S)-6'-甲氧基-9-金鸡宁]硫脲 作用下， 以 甲苯 为溶剂， 反应 16.0h， 生成 3-nitro-2-(4-bromophenyl)-2H-chromene 、 (S)-2-(4-bromophenyl)-3-nitro-2H-chromene
  参考文献：
  名称：

  双功能硫脲催化对映选择性合成2-Aryl-3-nitro-2H-chromenes

  摘要：

  双功能硫脲催化的oxa-Michael-aza-Henry-脱磺酰胺串联方法用于合成手性2-芳基-3-硝基-2H-色烯。该方法以中等至良好的产率和对映选择性直接获得相应的产品。

  DOI：

  10.1055/s-0030-1259956

文献信息

• Efficient kinetic resolution of racemic 3-nitro-2H-chromene derivatives catalyzed by Takemoto's organocatalyst
  作者：Jian-Wu Xie、Li-Ping Fan、Hong Su、Xin-Sheng Li、Dong-Cheng Xu

  DOI：10.1039/b922668k

  日期：——

  Efficient kinetic resolution of racemic 3-nitro-2H-chromenes by bifunctional thiourea afforded optically active (R)-3-nitro-2H-chromene derivatives with moderate to good enantioselectivities, which simultaneously gave the multifunctional 3,4-diphenyl-3a-nitrobenzopyrano-[3,4-c]-pyrrolidine-1,1-dicarboxylate derivatives with four vicinal chiral carbon centers.

  通过双官能硫脲对外消旋 3-硝基-2H-苯进行高效动力学解析，得到了具有光学活性的(R)-3-硝基-2H-苯衍生物，其对映体选择性为中等至良好，同时还得到了具有四个手性碳中心的多功能 3,4-二苯基-3a-硝基苯并吡喃-[3,4-c]-吡咯烷-1,1-二甲酸酯衍生物。
• The Role of L-Proline and Co-Catalysts in the Enantioselectivity of OXA-Michael-Henry Reactions
  作者：Lucas do Carmo、Simone Silva、Matheus Machado、Paloma Prata、Alberto Wisniewski Júnior、Diogo Vidal、José Augusto Villar

  DOI：10.21577/0103-5053.20180226

  日期：——

  The use of L-proline derivatives employed in OXA-Michael-Henry tandem reactions has been an efficient method to produce enantiomerically enriched compounds. In this work it was carried out a study of the OXA-Michael-Henry reactions between salicylaldehyde and beta-nitrostyrenes, catalyzed by L-proline and its derivatives. The corresponding (R)-3-nitro-2-phenyl-2H-chromenes were obtained in 55% enantiomeric excess (ee, 20 mol% L-proline) and 70% ee (stoichiometric amount) employing Ti((OPr)-Pr-i)(4) as Lewis acid. Despite the ee obtained, to the best of our knowledge, this result represents the highest enantioselectivity obtained in this reaction. Therefore, this work demonstrated that it is possible to obtain considerable enantiomeric excesses in OXA-Michael-Henry reactions using L-proline, an inexpensive and accessible amino acid.
• Asymmetric catalysis by l-prolinamide based small molecules: synthesis, characterization and first principle studies on their enantioselectivity
  作者：Dixita Rani、Mayank Khera、Neetu Goel、Jyoti Agarwal

  DOI：10.1016/j.mcat.2023.113185

  日期：2023.7
• Enantioselective Synthesis of 2-Aryl-3-nitro-2H-chromenes Catalyzed by a Bifunctional Thiourea
  作者：Peter Schreiner、Zhiguo Zhang、Gergely Jakab

  DOI：10.1055/s-0030-1259956

  日期：2011.6

  A bifunctional thiourea-catalyzed tandem approach of oxa-Michael―aza-Henry―desulfonamidation was used to synthesize chiral 2-aryl-3-nitro-2H-chromenes. This method provides direct access to the corresponding products in moderate to good yields and enantioselectivities.

  双功能硫脲催化的oxa-Michael-aza-Henry-脱磺酰胺串联方法用于合成手性2-芳基-3-硝基-2H-色烯。该方法以中等至良好的产率和对映选择性直接获得相应的产品。