6-bromo-2-phenyl-2H-chromene | 902835-95-4

• 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: 6-bromo-2-phenyl-2H-chromene
• CAS: 902835-95-4
• 化学式: C₁₅H₁₁BrO
• 分子量: 287.156
• InChiKey: JJZHGOBPUUAZTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  17
• 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：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  5-溴水杨醛 、 反式-苯乙烯三氟硼酸钾 在 二苄胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以71%的产率得到6-bromo-2-phenyl-2H-chromene
  参考文献：
  名称：

  Synthesis of 2-substituted 2H-chromenes using potassium vinyltrifluoroborates

  摘要：

  2H-Chromenes were synthesized from salicylaldehyde using potassium vinylic borates in the presence of secondary amines. We synthesized these 2H-chromene derivatives as a part of an ongoing project to develop inhibitors for TGF-beta receptors. Potassium vinyl trifluoroborates react with salicylaldehydes at 80 degrees C in the presence of a secondary amine and produced 2-substituted 2H-chromene derivatives with a 70-90% yield. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.01.008

文献信息

• Metalloradical Approach to 2<i>H</i>-Chromenes
  作者：Nanda D. Paul、Sutanuva Mandal、Matthias Otte、Xin Cui、X. Peter Zhang、Bas de Bruin

  DOI：10.1021/ja4111336

  日期：2014.1.22

  Cobalt(III)-carbene radicals, generated through metalloradical activation of salicyl N-tosylhydrazones by cobalt(II) complexes of porphyrins, readily undergo radical addition to terminal alkynes to produce salicyl-vinyl radical intermediates. Subsequent hydrogen atom transfer (HAT) from the hydroxy group of the salicyl moiety to the vinyl radical leads to the formation of 2H-chromenes. The Co(II)-catalyzed

  钴(III)-卡宾自由基是通过卟啉钴(II)配合物对水杨基N-甲苯磺酰腙进行金属自由基活化而产生的，很容易与末端炔进行自由基加成，产生水杨基-乙烯基自由基中间体。随后氢原子从水杨基部分的羟基转移(HAT)至乙烯基，导致2H-色烯的形成。Co(II) 催化的过程可以耐受各种取代模式，并以良好的分离收率生产相应的 2H-色烯产物。EPR 光谱和 TEMPO 自由基捕获实验与所提出的自由基机制一致。DFT 计算揭示了通过金属自由基介导的过程形成水杨基-乙烯基自由基中间体。出乎意料的是，随后从羟基部分到乙烯基的 HAT 导致形成邻醌甲基化物中间体，该中间体自发地从钴中心解离，并很容易进行环内、σ 闭环反应，形成最终的 2H-色烯产物。
• [EN] MITOCHONDRIAL INHIBITORS TO TREAT HUMAN DISEASE<br/>[FR] INHIBITEURS MITOCHONDRIAUX PERMETTANT DE TRAITER UNE MALADIE HUMAINE
  申请人：EINSTEIN COLL MED

  公开号：WO2010120337A1

  公开（公告）日：2010-10-21

  The present invention relates to inhibitors of mitochondria-associated, granulocyte- macrophage colony stimulating factor signaling molecule (Magmas), and related compositions and uses thereof.

  本发明涉及线粒体相关的粒细胞-巨噬细胞集落刺激因子信号分子（Magmas）的抑制剂，以及相关的组合物和用途。
• Synthesis of 2H-chromenes and 1,2-dihydroquinolines from aryl aldehydes, amines, and alkenylboron compounds
  作者：Nicos A. Petasis、Alexey N. Butkevich

  DOI：10.1016/j.jorganchem.2008.11.050

  日期：2009.5

  The one-step reaction of salicylaldehydes with amines and alkenyl boronic acids or alkenyl trifluoroborates to form 2H-chromenes (2H-1-benzopyrans) has been investigated in more detail and new suitable conditions have been identified, including the use of tertiary amines and protic solvents including water. This process was applied to a concise synthesis of a tocopherol analog. The analogous condensation reaction between 2-sulfamidobenzaldehydes and alkenyl trifluoroborates provides an efficient synthesis of 1,2-dihydroquinoline derivatives. (C) 2008 Elsevier B.V. All rights reserved.
• MITOCHONDRIAL INHIBITORS TO TREAT HUMAN DISEASE
  申请人：Jubinsky Paul

  公开号：US20120093728A1

  公开（公告）日：2012-04-19

  The present invention relates to inhibitors of mitochondria-associated, granulocyte-macrophage colony stimulating factor signaling molecule (Magmas), and related compositions and uses thereof.
• US8581005B2
  申请人：——

  公开号：US8581005B2

  公开（公告）日：2013-11-12