(Z)-ethyl 3-(4-bromophenyl)-2-nitroacrylate | 1255517-01-1

• 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-(4-bromophenyl)-2-nitroacrylate
• 英文别名: (Z)-ethyl 3-(4-bromophenyl)-2-nitropropenoate；ethyl 3-(4-bromophenyl)-2-nitroacrylate；z-Ethyl 3-(4-bromophenyl)-2-nitropropenoate；ethyl (Z)-3-(4-bromophenyl)-2-nitroprop-2-enoate
• CAS: 1255517-01-1
• 化学式: C₁₁H₁₀BrNO₄
• 分子量: 300.109
• InChiKey: ZBQHHABAEMBGCT-YFHOEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  (Z)-ethyl 3-(4-bromophenyl)-2-nitroacrylate 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 以86%的产率得到ethyl 5-(4-bromophenyl)-1,2,3-triazole-4-carboxylate
  参考文献：
  名称：

  与叠氮化钠反应时，经Geminally活化的硝基乙烯。官能化的1,2,3-三唑的合成

  摘要：

  双键活化的烷氧基羰基（乙酰基，苯甲酰基，氰基）硝基乙烯与叠氮化钠的反应提供了一系列功能取代的1,2,3-三唑。它们的结构通过IR，1 H和13 C– { 1 H} NMR光谱表征。

  DOI：

  10.1134/s1070363216060086
• 作为产物：
  描述：

  对溴苯甲醛 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-(4-bromophenyl)-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

• Monofluorinated 5-membered rings <i>via</i> fluoromethylene transfer: synthesis of monofluorinated isoxazoline <i>N</i>-oxides
  作者：Arturs Sperga、Armands Kazia、Janis Veliks

  DOI：10.1039/d1ob00270h

  日期：——

  The synthesis of five-membered rings using fluoromethylene transfer chemistry is an attractive method for building fluorinated products of high value. This work demonstrates for the first time that one-fluorine-one-carbon modification of a substrate could be a viable strategy to access monofluorinated five-membered rings. The synthetic methodology was developed to access monofluorinated isoxazoline-N-oxides

  使用氟代亚甲基转移化学方法合成五元环是构建高价值氟化产物的一种有吸引力的方法。这项工作首次证明，对基材进行单氟单碳修饰可能是访问单氟化五元环的可行策略。开发了一种合成方法，可使用氟甲基s试剂从取代的2-硝基丙烯酸酯开始，一步获得单氟化异恶唑啉-N-氧化物。
• Catalytic Asymmetric Formal [4 + 1] Annulation Leading to Optically Active <i>cis</i>-Isoxazoline <i>N</i>-Oxides
  作者：Zugui Shi、Bin Tan、Wendy Wen Yi Leong、Xiaofei Zeng、Min Lu、Guofu Zhong

  DOI：10.1021/ol102181r

  日期：2010.12.3

  The catalytic asymmetric synthesis of densely functionalized cis-isoxazoline N-oxides was realized with novel use of an organocatalyst, (S)-2-(azidodiphenylmethyl)pyrrolidine (4e) (Tan, B.; Zhu, D.; Zhang, L.; Chua, P. J.; Zeng, X.; Zhong, G. Chem.-Eur. J. 2010, 16, 3842; Olivares-Romero, J. L.; Juaristi, E. Tetrahedron 2008, 64, 9992), via an elegant formal [4 + 1] annulation strategy using readily available 2-nitroacrylates and alpha-iodoaldehydes.
• Asymmetric Friedel–Crafts alkylation of indoles with 2-nitro-3-arylacrylates catalyzed by a metal-templated hydrogen bonding catalyst
  作者：Jingfen Liu、Lei Gong、Eric Meggers

  DOI：10.1016/j.tetlet.2015.06.046

  日期：2015.8

  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.
• Geminally activated nitroethenes in reactions with sodium azide. Synthesis of functionalized 1,2,3-triazoles
  作者：V. M. Berestovitskaya、R. I. Baichurin、N. I. Aboskalova、L. V. Baichurina、E. V. Trukhin、A. V. Fel’gendler、M. A. Gensirovskaya

  DOI：10.1134/s1070363216060086

  日期：2016.6

  Reactions of geminally activated alkoxycarbonyl(acetyl, benzoyl, cyano)nitroethenes with sodium azide provided a series of functionally substituted 1,2,3-triazoles. Their structure was characterized by IR, 1H, and 13C–1H} NMR spectroscopy.

  双键活化的烷氧基羰基（乙酰基，苯甲酰基，氰基）硝基乙烯与叠氮化钠的反应提供了一系列功能取代的1,2,3-三唑。它们的结构通过IR，1 H和13 C– 1 H} NMR光谱表征。