1-(1-bromobut-3-en-1-yl)-4-nitrobenzene | 1391057-12-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(1-bromobut-3-en-1-yl)-4-nitrobenzene
• CAS: 1391057-12-7
• 化学式: C₁₀H₁₀BrNO₂
• 分子量: 256.099
• InChiKey: ABEDTRHOLFWHCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  43.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-(1-bromobut-3-en-1-yl)-4-nitrobenzene 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-1-(buta-1,3-dien-1-yl)-4-nitrobenzene
  参考文献：
  名称：

  三卤化硼介导的芳醛的卤代烯丙基化及其在（E）-1,3-二烯制备中的应用

  摘要：

  在三卤化硼存在下，芳基醛容易与烯丙基金属偶合，得到卤代烯丙基化产物。反应可耐受多种官能团。简单的卤代烯丙基化反应的水性处理，然后用1,8-二氮杂双环[5.4.0] undec-7-ene处理，为合成有用的（E）-1,3-二烯提供了直接途径。温和的反应条件，容易获得的起始原料以及高的立体选择性使这种两步式（E）-1,3-二烯合成非常有吸引力。 三卤化硼-烯丙基金属-卤代烯丙基-二烯-立体选择性

  DOI：

  10.1055/s-0031-1289304
• 作为产物：
  描述：

  1-(4-硝基苯基)丁-3-烯-1-醇 在 三溴化磷 作用下， 以 乙醚 为溶剂， 以36%的产率得到1-(1-bromobut-3-en-1-yl)-4-nitrobenzene
  参考文献：
  名称：

  Carbene-Catalyzed Reductive Coupling of Nitrobenzyl Bromide and Nitroalkene via the Single-Electron-Transfer (SET) Process and Formal 1,4-Addition

  摘要：

  A carbene-catalyzed reductive 1,4-addition of nitrobenzyl bromides to nitroalkenes is disclosed. The reaction proceeds via a carbene-enabled single-electron-transfer process that generates radicals as key intermediates. The present study expands the potentials of carbene catalysis and offers unusual transformations for common substrates in organic synthesis.

  DOI：

  10.1021/acs.orglett.6b03792

文献信息

• Synthesis of indanes via carbene-catalyzed single-electron-transfer processes and cascade reactions
  作者：Yuhuang Wang、Xingxing Wu、Yonggui Robin Chi

  DOI：10.1039/c7cc07208b

  日期：——

  carbene-catalyzed cascade reaction is developed for the synthesis of multi-substituted indane derivatives. The reaction involves two sequential Michael-addition steps, of which the first step is enabled by an NHC-mediated radical process. This work demonstrates the synthetic potentials of NHC-mediated single-electron-transfer processes for efficient reactions and rapid synthesis.

  开发了卡宾催化的级联反应，用于合成多取代的茚满衍生物。该反应涉及两个连续的迈克尔加成步骤，其中第一步是通过NHC介导的自由基过程实现的。这项工作证明了NHC介导的单电子转移过程对于有效反应和快速合成的合成潜力。
• Toward a fragment-based approach to MMPs inhibitors: an expedite and efficient synthesis of N-hydroxylactams
  作者：Francesco Leonetti、Giovanni Muncipinto、Angela Stefanachi、Orazio Nicolotti、Saverio Cellamare、Marco Catto、Leonardo Pisani、Giovanni Pellegrino、Angelo Carotti

  DOI：10.1016/j.tetlet.2012.05.124

  日期：2012.8

  Matrix metalloproteinases (MMPs), a class of zinc-enzymes over-activated in many pathologies, such as arthritis and cancer, can be efficiently inhibited by a variety of molecules bearing zinc-binding groups (ZBGs). The hydroxamic acid moiety represents one of the most potent and widely exploited ZBG but the poor target selectivity and in vivo toxicity have tempered the initial enthusiasm for this class of potential therapeutics. These drawbacks might be circumvented, at least in part, by increasing the structural constraints around the hydroxamic moiety. Following this strategy we designed and prepared N-hydroxylactam molecules of different size through a synthetic protocol based on a ring closing metathesis amenable to a fragment-based approach potentially leading to a large molecular diversity. (C) 2012 Elsevier Ltd. All rights reserved.