ethyl 2-((2S,3R,4S)-4-((2-hydroxyphenyl)amino)-3-methyl-3-nitrochroman-2-yl)acetate | 1266339-54-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-((2S,3R,4S)-4-((2-hydroxyphenyl)amino)-3-methyl-3-nitrochroman-2-yl)acetate
• 英文别名: ethyl 2-[(2S,3R,4S)-4-(2-hydroxyanilino)-3-methyl-3-nitro-2,4-dihydrochromen-2-yl]acetate
• CAS: 1266339-54-1
• 化学式: C₂₀H₂₂N₂O₆
• 分子量: 386.404
• InChiKey: OFAYLSPBZBLDOB-IHPCNDPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (E)-ethyl 3-(2-((E)-2-nitroprop-1-enyl)phenoxy)acrylate 、 2-氨基苯酚 在 thiourea catalyst 作用下， 以 异丙醇 为溶剂， 反应 6.0h， 以98%的产率得到ethyl 2-((2S,3R,4S)-4-((2-hydroxyphenyl)amino)-3-methyl-3-nitrochroman-2-yl)acetate
  参考文献：
  名称：

  Catalytic Asymmetric Aza-Michael−Michael Addition Cascade: Enantioselective Synthesis of Polysubstituted 4-Aminobenzopyrans

  摘要：

  A catalytic asymmetric aza-Michael-Michael addition cascade of anilines to nitroolefin enoates in the presence of chiral bifunctional thiourea catalysts has been disclosed. This reaction provides a mild and efficient approach to polysubstituted chiral 4-aminobenzopyrans bearing three consecutive stereocenters in high yields with excellent stereoselectivities.

  DOI：

  10.1021/ol1031188

文献信息

• Organocatalytic Asymmetric Sulfa-Michael/Michael Addition Reactions: A Strategy for the Synthesis of Highly Substituted Chromans with a Quaternary Stereocenter
  作者：Xu-Fan Wang、Qiu-Lin Hua、Ying Cheng、Xiao-Lei An、Qing-Qing Yang、Jia-Rong Chen、Wen-Jing Xiao

  DOI：10.1002/anie.201004534

  日期：2010.11.2

  Simply complex: Diverse and structurally complex chroman derivatives with a quaternary stereocenter have been obtained through the titled reaction of thiols with nitroolefin enoates using the bifunctional catalyst 1. The reaction features simple experimental procedures, high yield, enantiomeric excess, and excellent diastereoselectivity.

  简单复杂：使用双功能催化剂1，通过巯基与硝基烯烃烯酸酯的标题反应，获得了具有四级立体中心的多样且结构复杂的苯并二氢吡喃衍生物。该反应具有简单的实验步骤，高收率，对映体过量和优异的非对映选择性。
• Catalytic Asymmetric Aza-Michael−Michael Addition Cascade: Enantioselective Synthesis of Polysubstituted 4-Aminobenzopyrans
  作者：Xu-Fan Wang、Jing An、Xiao-Xiao Zhang、Fen Tan、Jia-Rong Chen、Wen-Jing Xiao

  DOI：10.1021/ol1031188

  日期：2011.2.18

  A catalytic asymmetric aza-Michael-Michael addition cascade of anilines to nitroolefin enoates in the presence of chiral bifunctional thiourea catalysts has been disclosed. This reaction provides a mild and efficient approach to polysubstituted chiral 4-aminobenzopyrans bearing three consecutive stereocenters in high yields with excellent stereoselectivities.