(Z)-ethyl 3-(naphthalen-2-yl)-2-nitroacrylate | 60859-83-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (Z)-ethyl 3-(naphthalen-2-yl)-2-nitroacrylate
• 英文别名: ethyl (Z)-3-naphthalen-2-yl-2-nitroprop-2-enoate
• CAS: 60859-83-8
• 化学式: C₁₅H₁₃NO₄
• 分子量: 271.273
• InChiKey: YHQJMLCTEMYLGW-UVTDQMKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  吲哚 、 (Z)-ethyl 3-(naphthalen-2-yl)-2-nitroacrylate 在 C₄₆H₄₁F₃IrN₈O₃S₂⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-) 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以92%的产率得到
  参考文献：
  名称：

  Asymmetric Friedel–Crafts alkylation of indoles with 2-nitro-3-arylacrylates catalyzed by a metal-templated hydrogen bonding catalyst

  摘要：

  An asymmetric Friedel-Crafts alkylation of indoles with 2-nitro-3-arylacrylates catalyzed by a metal-templated hydrogen bonding catalyst has been established. The asymmetric induction relies on chirality transfer solely from the octahedral metal stereocenter via three weak hydrogen bonds. All the products are provided with good to excellent enantioselectivities while modest diastereoselectivities, which can be converted into a variety of valuable indole-containing chiral building blocks including tryptophan derivatives. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.06.046
• 作为产物：
  描述：

  2-萘甲醛 在 乙酸酐 、 magnesium sulfate 作用下， 以 四氢呋喃 为溶剂， 反应 22.0h， 生成 (Z)-ethyl 3-(naphthalen-2-yl)-2-nitroacrylate
  参考文献：
  名称：

  Asymmetric Friedel–Crafts alkylation of indoles with 2-nitro-3-arylacrylates catalyzed by a metal-templated hydrogen bonding catalyst

  摘要：

  An asymmetric Friedel-Crafts alkylation of indoles with 2-nitro-3-arylacrylates catalyzed by a metal-templated hydrogen bonding catalyst has been established. The asymmetric induction relies on chirality transfer solely from the octahedral metal stereocenter via three weak hydrogen bonds. All the products are provided with good to excellent enantioselectivities while modest diastereoselectivities, which can be converted into a variety of valuable indole-containing chiral building blocks including tryptophan derivatives. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.06.046

文献信息

• Amides as surrogates of aldehydes for C-C bond formation: amide-based direct Knoevenagel-type condensation reaction and related reactions
  作者：Wei Ou、Pei-Qiang Huang

  DOI：10.1007/s11426-019-9586-3

  日期：2020.1

  Aldehydes are perhaps the most versatile compounds that enable many C-C bond forming reactions, which are not amenable for other subclasses of carbonyl compounds. We report the first use of amides as surrogates of aldehydes for C-C bond formation, namely, the direct Knoevenagel-type condensation based on amides. The one-pot method consists of controlled reduction of an amide with LDBIPA [LiAlH(iBu)2(OiPr)]

  醛也许是最能实现许多CC键形成反应的多功能化合物，这些不适用于羰基化合物的其他亚类。我们报道了酰胺的首次使用作为CC代形成醛的替代品，即基于酰胺的直接Knoevenagel型缩合反应。一锅法包括用LDBIPA [LiAlH（i Bu）2（O i Pr）]控制酰胺还原，路易斯酸介导的反应性亚胺离子中间体的释放，亲核加成和原位反应消除胺。该反应显示出良好的官能团耐受性。我们还证明了Schwartz试剂可以用作LDBIPA的替代品。使用硝基甲烷和甲硅烷基烯醇醚作为亲核试剂分别为空前的基于酰胺的硝基-羟醛缩合反应和羟醛缩合反应开辟了道路。