6-nitro-4H-chromene | 1133728-83-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-nitro-4H-chromene
• 英文别名: 6-Nitro-2H-chromen
• CAS: 1133728-83-2
• 化学式: C₉H₇NO₃
• 分子量: 177.159
• InChiKey: VYDSLQQERGDWSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-nitro-4H-chromene 、 4-methoxybenzenediazonium tetrafluoroborate 在 2,6-二叔丁基-4-甲基吡啶 、 palladium diacetate 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 2.5h， 以53%的产率得到2-(4-methoxyphenyl)-6-nitro-2H-chromene
  参考文献：
  名称：

  The scope of the Heck arylation of enol ethers with arenediazonium salts: a new approach to the synthesis of flavonoids

  摘要：

  The scope of the Heck arylation of cyclic and acyclic enol ethers with arenediazonium salts was evaluated. Arylation of 2,3-dihydrofuran yielded 2-aryl-2,5-dihydrofurans as the major adducts (>99:1) except when using n-Bu4NHSO4 as additive or 4-NO2PhN2BF4 as arenediazonium salt. 2,3-Dihydropyran provided mixtures of the three possible isomeric Heck adducts. Arylation of n-butylvinylether with arenediazonium bearing electron-donating groups resulted in substituted acetophenones as almost exclusive products in good overall yields, Substituted 4H-chromenes provided 2-aryl-2H-chromenes in moderate yield when applying the Pd(OAc)(2)/2,6-di-t-butyl-4-methylpyridine catalytic system, which were applied in the synthesis of flavonoids. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.01.017
• 作为产物：
  描述：

  2-allyl-4-nitro-1-(vinyloxy)benzene 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以91%的产率得到6-nitro-4H-chromene
  参考文献：
  名称：

  The scope of the Heck arylation of enol ethers with arenediazonium salts: a new approach to the synthesis of flavonoids

  摘要：

  The scope of the Heck arylation of cyclic and acyclic enol ethers with arenediazonium salts was evaluated. Arylation of 2,3-dihydrofuran yielded 2-aryl-2,5-dihydrofurans as the major adducts (>99:1) except when using n-Bu4NHSO4 as additive or 4-NO2PhN2BF4 as arenediazonium salt. 2,3-Dihydropyran provided mixtures of the three possible isomeric Heck adducts. Arylation of n-butylvinylether with arenediazonium bearing electron-donating groups resulted in substituted acetophenones as almost exclusive products in good overall yields, Substituted 4H-chromenes provided 2-aryl-2H-chromenes in moderate yield when applying the Pd(OAc)(2)/2,6-di-t-butyl-4-methylpyridine catalytic system, which were applied in the synthesis of flavonoids. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.01.017

文献信息

• [EN] GLYCOPROTEIN IIb/IIIa ANTAGONISTS<br/>[FR] ANTAGONISTES DE LA GLYCOPROTEINE IIb/IIIa
  申请人：ELI LILLY AND COMPANY

  公开号：WO1996022288A1

  公开（公告）日：1996-07-25

  (EN) This invention relates to certain bicyclic compounds having a nucleus formed of two fused six membered rings, for example, benzopyran, isoquinoline, isoquinolone, tetrahydronaphthalene, dihydronaphthalene, or tetralone, substituted with both basic and acidic functionality, which are useful in inhibition of platelet aggregation.(FR) Cette invention se rapporte à certains composés bicycliques possédant un noyau constitué de deux cycles hexagonaux fusionnés, par exemple, benzopyrane, isoquinoline, isoquinolone, tétrahydronaphtalène, dihydronaphtalène ou tétralone, remplacés par une fonctionnalité à la fois basique et acide. Ces composés sont utilisés dans l'inhibition de l'agrégation plaquettaire.

  该发明涉及某些具有由两个融合的六元环组成的核的双环化合物，例如苯并吡喃、异喹啉、异喹啉酮、四氢萘、二氢萘或四酮，被基础和酸性官能团取代，可用于抑制血小板聚集。
• Glycoprotein llb/llla antagonists
  申请人：——

  公开号：US20030130342A1

  公开（公告）日：2003-07-10

  This invention relates to certain bicyclic compounds having a nucleus formed of two fused six membered rings, for example, benzopyran, isoquinoline, isoquinolone, tetrahydronaphthalene, dihydronaphthalene, or tetralone, substituted with both basic and acidic functionality, which are useful in inhibition of platelet aggregation.

  本发明涉及某些自行车环化合物，其核由两个融合的六元环组成，例如苯并吡喃，异喹啉，异喹啉酮，四氢萘，二氢萘或四酮，同时带有酸性和碱性官能团，对于抑制血小板聚集具有用处。
• Synthesis of benzofurans via Pd2+-catalyzed oxidative cyclization of 2-allylphenols
  作者：Alexander I. Roshchin、Sergey M. Kel’chevski、Nikolai A. Bumagin

  DOI：10.1016/s0022-328x(98)00415-x

  日期：1998.6

  Substituted 2-methylbenzofurans were obtained from 2-allylphenols via Pd2+-catalyzed oxidative cyclization using Cu(OAc)(2)LiCl as a reoxidant and wet DMF as a solvent. (C) 1998 Elsevier Science S.A. All rights reserved.
• GLYCOPROTEIN IIb/IIIa ANTAGONISTS
  申请人：ELI LILLY AND COMPANY

  公开号：EP0804431B1

  公开（公告）日：2002-07-24
• EP0804431A4
  申请人：——

  公开号：EP0804431A4

  公开（公告）日：1998-04-29