2-碘-4-甲氧基-1,1'-联苯 | 481071-90-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-碘-4-甲氧基-1,1'-联苯
• 英文名称: 2-iodo-4-methoxybiphenyl
• 英文别名: 2-iodo-4-methoxy-1,1'-biphenyl；2-iodo-4-methoxy-1,1′-biphenyl；2-Iodo-4-methoxy-1-phenylbenzene；2-iodo-4-methoxy-1-phenylbenzene
• CAS: 481071-90-3
• 化学式: C₁₃H₁₁IO
• 分子量: 310.134
• InChiKey: KQKPAZKMNIQCSD-UHFFFAOYSA-N

物化性质

• 沸点：
  376.4±35.0 °C(Predicted)
• 密度：
  1.544±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-碘-4-甲氧基-1,1'-联苯 在 copper diacetate 、 sodium carbonate 、 乙二醇 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 17.0h， 生成 2-methoxy-9-tosyl-9H-carbazole
  参考文献：
  名称：

  通过将一锅铜催化的胺插入环状二苯并碘鎓中来合成咔唑，作为生成类似药物的化学文库的策略

  摘要：

  AbstractCarbazoles have attracted high interest among synthetic chemists due to their unique structural features and potential pharmacological activities. Compared to linear aryliodoniums, cyclic diphenyleneiodoniums are more inert and have not attracted much attention to their application as building blocks. Employing our synthetic strategy, diversified carbazoles can be efficiently obtained from a single cyclic diphenyleneiodonium under mild conditions. The reactions catalyzed by copper(II) acetate have provided a variety of carbazoles in modest to good yields with a broad range of amines including anilines, aliphatic amines and sulfonamides. Moreover, one of the obtained carbazoles has displayed an outstanding ability to protect HT‐22 neuronal cells from the damage induced by neurotoxins glutamate and homocysteic acid.magnified image

  DOI：

  10.1002/adsc.201300271
• 作为产物：
  描述：

  2-amino-4-methoxybiphenyl 在 盐酸 、 sodium nitrite 、 potassium iodide 作用下， 以 水 为溶剂， 生成 2-碘-4-甲氧基-1,1'-联苯
  参考文献：
  名称：

  室温磷光合成含碲的π扩展芳香族化合物。

  摘要：

  已经开发了由碲粉和容易获得的环状二芳基碘鎓盐合成嵌入碲的π-延伸的芳族化合物。该方法的多功能性已通过合成各种功能化的二苯并二氮杂吩（DBTe's），梯型π-系统和异丁二烯烯来证明。这些化合物表现出良好的空气/水分稳定性和高热稳定性。值得注意的是，许多DBTe在固态下均表现出令人感兴趣的可调室温磷光（RTP）。

  DOI：

  10.1021/acs.orglett.9b03106

文献信息

• Recyclable copper catalyzed nitrogenation of biphenyl halides: a direct approach to carbazoles
  作者：Yang Ou、Ning Jiao

  DOI：10.1039/c3cc41443d

  日期：——

  A novel A21-CuI catalyzed direct nitrogenation of biphenyl halides for the direct synthesis of carbazoles via a direct C–H amination process has been developed. A recyclable and inexpensive Cu-catalyst was successfully employed in N-heterocyclic compound synthesis via tandem azidation and C–H amination, which makes this protocol very practical and easy to handle.

  一种新型的A21-CuI催化的二苯基卤化物的直接氮化反应已被开发，用于通过直接C–H氨化反应合成卡巴唑。成功使用了一种可回收且廉价的铜催化剂，通过串联叠氮化和C–H氨化合成N-杂环化合物，使这一方法非常实用且容易操作。
• Two-in-one strategy for fluorene-based spirocycles<i>via</i>Pd(0)-catalyzed spiroannulation of<i>o</i>-iodobiaryls with bromonaphthols
  作者：Bojun Tan、Long Liu、Huayu Zheng、Tianyi Cheng、Dianhu Zhu、Xiaofeng Yang、Xinjun Luan

  DOI：10.1039/d0sc04386a

  日期：——

  Rapid assembly of fluorene-based spirocycles represents a highly significant but challenging task in organic synthesis. Reported herein is a novel Pd(0)-catalyzed [4+1] spiroannulation of simple o-iodobiaryls with bromonaphthols for the one-step construction of [4,5]-spirofluorenes in high yields with excellent functional group tolerance. Noteworthily, these valuable fluorene-based coumarin skeletons

  芴基螺环的快速组装代表了有机合成中非常重要但具有挑战性的任务。本文报道的是一种新颖的Pd（0）催化的简单邻碘二芳基与溴酚合成的Pd（0）螺环化，用于一步合成高纯度[4,5]-螺芴并具有出色的官能团耐受性。值得注意的是，这些有价值的芴基香豆素骨架可以丰富C-香豆素的数据库，并具有出色的光谱性能。
• Synthesis of Tribenzo[<i>b</i>,<i><i>d</i></i>,<i>f</i>]azepines via Palladium-Catalyzed Annulation Reaction of 2-Iodobiphenyls with 2-Halogenoanilines
  作者：Mao-Ying Fang、Li-Ping Chen、Lin Huang、Dong-Mei Fang、Xiao-Zhen Chen、Bi-Qin Wang、Chun Feng、Shi-Kai Xiang

  DOI：10.1021/acs.joc.1c01082

  日期：2021.7.2

  with 2-halogenoanilines has been developed. A variety of 2-iodobiphenyls and 2-halogenoanilines can undergo this transformation. Diversified tribenzo[b,d,f]azepine derivatives can be synthesized in moderate to excellent yields according to this method.

  已开发出钯催化的 2-碘联苯与 2-卤代苯胺的环化反应。多种 2-碘联苯和 2-卤代苯胺都可以进行这种转化。根据该方法可以以中等至优异的产率合成多样化的三苯并[ b、d、f ]氮杂衍生物。
• Aryl to Aryl Palladium Migration in the Heck and Suzuki Coupling of <i>o</i>-Halobiaryls
  作者：Marino A. Campo、Haiming Zhang、Tuanli Yao、Abdellatif Ibdah、Ryan D. McCulla、Qinhua Huang、Jian Zhao、William S. Jenks、Richard C. Larock

  DOI：10.1021/ja069238z

  日期：2007.5.1

  A novel 1,4-palladium migration between the o- and o'-positions of biaryls has been observed in organopalladium intermediates derived from o-halobiaryls. The organopalladium intermediates generated by this migration have been trapped either by a Heck reaction employing ethyl acrylate or by Suzuki cross-coupling using arylboronic acids. This palladium migration can be activated or deactivated by choosing the appropriate reaction conditions. Chemical and computational evidence supports the presence of an equilibrium that correlates with the C-H acidity of the available arene positions.
• Novel 1,4-Palladium Migration in Organopalladium Intermediates Derived from <i>o</i>-Iodobiaryls
  作者：Marino A. Campo、Richard C. Larock

  DOI：10.1021/ja027548l

  日期：2002.12.1

  A novel 1,4-palladium migration in organopalladium intermediates derived from o-iodobiaryls has been observed under modified Heck reaction conditions. This migration process can be switched "on" or "off" by simply choosing the appropriate reaction conditions.