(E)-4-(1-Bromo-2-naphthalenyl)-3-buten-2-one | 159305-88-1

• 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: (E)-4-(1-Bromo-2-naphthalenyl)-3-buten-2-one
• 英文别名: (E)-4-(1-bromonaphthalen-2-yl)but-3-en-2-one
• CAS: 159305-88-1
• 化学式: C₁₄H₁₁BrO
• 分子量: 275.145
• InChiKey: GEXWHJDCIQBUOU-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-4-(1-Bromo-2-naphthalenyl)-3-buten-2-one 在 palladium on activated charcoal 偶氮二异丁腈 、 氢气 、 三正丁基氢锡 作用下， 以 乙酸乙酯 、 苯 为溶剂， 反应 8.0h， 生成 4-(naphthalen-2-yl)butan-2-one
  参考文献：
  名称：

  Enediyne- and Tributyltin Hydride-Mediated Aryl Radical Additions onto Various Radical Acceptors

  摘要：

  Tandem enediyne-radical cyclizations were carried out on substrates that contain nitrile and ketone radical accepters. The products of these cyclizations and the previously reported tandem enediyne-radical cyclizations containing aldehyde and oxime ether radical accepters were compared with tributyltin hydride-mediated aryl radical addition reactions with 1-bromonaphthalene derivatives containing aldehyde, oxime ether, nitrile, and ketone radical accepters, since these substrates go through similar initial radical intermediates. Although many of the same products were observed using either method of aryl radical generation, there were distinct differences in the product composition and identity depending on which method was used. These differences can probably be primarily attributed to the temperature difference of the two modes of radical generation.

  DOI：

  10.1021/jo00104a053
• 作为产物：
  描述：

  2-羟甲基-1-溴萘 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 5.0h， 生成 (E)-4-(1-Bromo-2-naphthalenyl)-3-buten-2-one
  参考文献：
  名称：

  Enediyne- and Tributyltin Hydride-Mediated Aryl Radical Additions onto Various Radical Acceptors

  摘要：

  Tandem enediyne-radical cyclizations were carried out on substrates that contain nitrile and ketone radical accepters. The products of these cyclizations and the previously reported tandem enediyne-radical cyclizations containing aldehyde and oxime ether radical accepters were compared with tributyltin hydride-mediated aryl radical addition reactions with 1-bromonaphthalene derivatives containing aldehyde, oxime ether, nitrile, and ketone radical accepters, since these substrates go through similar initial radical intermediates. Although many of the same products were observed using either method of aryl radical generation, there were distinct differences in the product composition and identity depending on which method was used. These differences can probably be primarily attributed to the temperature difference of the two modes of radical generation.

  DOI：

  10.1021/jo00104a053

文献信息

• Nickel-Catalyzed Cross-Electrophile Coupling Reactions between Allylic Acetates and <i>gem</i>-Difluorovinyl Tosylate
  作者：Xiaochun He、Jiangjun Liu、Gang Chen、Baojian Xiong、Xue Xiao、Lei Chen、Xuemei Zhang、Lin Dong、Xuelei Ma、Zhong Lian

  DOI：10.1021/acs.orglett.2c01245

  日期：2022.5.20

  A nickel-catalyzed cross-electrophile coupling of allylic acetates and gem-difluorovinyl tosylate is presented, which first achieves allylic gem-difluoroolefins via C(sp3)–C(sp2) cross-electrophile coupling. In addition, this protocol was performed under mild reaction conditions, affording a variety of allylic gem-difluorovinyl arenes in moderate to good yields. Moreover, both linear and branched allylic

  提出了一种镍催化的烯丙基乙酸酯和偕二氟乙烯基甲苯磺酸酯的交叉亲电偶联，它首先通过C(sp 3 )–C(sp 2 ) 交叉亲电偶联实现了烯丙基偕二氟烯烃。此外，该协议是在温和的反应条件下进行的，以中等至良好的产率提供各种烯丙基宝石-二氟乙烯基芳烃。此外，直链和支链的烯丙基乙酸酯都可以单独产生直链交叉偶联产物。机理研究表明，该反应涉及两个不同的 Ni(0)/Ni(II) 催化循环。
• Enediyne- and Tributyltin Hydride-Mediated Aryl Radical Additions onto Various Radical Acceptors
  作者：Janet Wisniewski Grissom、Detlef Klingberg、Sabine Meyenburg、Brenda L. Stallman

  DOI：10.1021/jo00104a053

  日期：1994.12

  Tandem enediyne-radical cyclizations were carried out on substrates that contain nitrile and ketone radical accepters. The products of these cyclizations and the previously reported tandem enediyne-radical cyclizations containing aldehyde and oxime ether radical accepters were compared with tributyltin hydride-mediated aryl radical addition reactions with 1-bromonaphthalene derivatives containing aldehyde, oxime ether, nitrile, and ketone radical accepters, since these substrates go through similar initial radical intermediates. Although many of the same products were observed using either method of aryl radical generation, there were distinct differences in the product composition and identity depending on which method was used. These differences can probably be primarily attributed to the temperature difference of the two modes of radical generation.