2,5-二碘-1,3-二甲苯 | 4102-48-1

• 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: 2,5-二碘-1,3-二甲苯
• 英文名称: 1,4-diiodo-2,6-dimethylbenzene
• 英文别名: 2,5-diiodo-1,3-dimethylbenzene；2,5-Diiod-m-xylol；2,5-Dijod-m-xylol
• CAS: 4102-48-1
• 化学式: C₈H₈I₂
• 分子量: 357.961
• InChiKey: VOEUAVLLUTWZPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2903999090

反应信息

• 作为反应物：
  描述：

  2,5-二碘-1,3-二甲苯 、 丙二腈 在 六甲基磷酰三胺 、 copper(l) iodide 、 sodium hydride 作用下， 生成 2-iodo-5-(dicyanomethyl)-1,3-dimethylbenzene
  参考文献：
  名称：

  New electron acceptors: synthesis, electrochemistry, and radical anions of N,7,7-tricyanoquinomethanimines and x-ray crystal structures of the trimethyl and tetramethyl derivatives

  摘要：

  The reaction of a range of quinones 3 with malononitrile in the presence of titanium tetrachloride/pyridine yields dicyanoquinomethides 4, which on reaction with N,N'-bis(trimethylsilyl)carbodiimide are converted into the corresponding N,7,7-tricyanoquinomethanimines 6. The solution electrochemical redox properties of compounds 6 have been studied by cyclic voltammetry; they are strong acceptors which readily form radical anions and dianions. The radical anions of N,7,7-tricyanoquinodimethanimine 6a and the tetra-, tri- and dimethyl derivatives 6c, 6d, and 6e, respectively, have been studied by ESR and ENDOR spectroscopy. X-ray crystal structure analysis reveals that trimethyl derivative 6d is planar, whereas the tetramethyl derivative 6c is strongly deformed with the ring existing in a boat conformation, similar to that found previously for tetrasubstituted TCNQ derivatives.

  DOI：

  10.1021/jo00032a017
• 作为产物：
  描述：

  4-碘-2,6-二甲基苯胺 生成 2,5-二碘-1,3-二甲苯
  参考文献：
  名称：

  四种异构二碘间二甲苯的合成。它们在硫酸和多聚磷酸中的异构化

  摘要：

  已合成了四种异构二碘间二甲苯，并研究了它们在浓酸中的异构化，以阐明在 2-碘间二甲苯的雅各布森反应中观察到的新重排机制。2,4- 和 4,5- 二碘间二甲苯在冷硫酸或热多磷酸存在下，分别异构化为 4,6- 和 2,5- 二碘间二甲苯。所有四种异构体都容易与热硫酸发生歧化反应，得到三和四碘间二甲苯的混合物。在与多磷酸的反应中未观察到歧化。已经讨论了磺基在该反应中所起的重要作用。

  DOI：

  10.1246/bcsj.38.1590

文献信息

• Copper(I) Phenoxide Complexes in the Etherification of Aryl Halides
  作者：Jesse W. Tye、Zhiqiang Weng、Ramesh Giri、John F. Hartwig

  DOI：10.1002/anie.200902245

  日期：2010.3.15

  No copping out! Copper(I) phenoxide complexes containing chelating ligands (see picture), proposed intermediates in copper‐catalyzed etherification of aryl halides, have been synthesized and fully characterized. The kinetic and chemical competence of the isolated complexes are demonstrated for the synthesis of aryl phenyl ethers, and experiments provide evidence against mechanistic pathways involving

  无处遁形！含有螯合配体的苯酚铜（I）络合物（见图）是铜催化芳基卤化物醚化的中间体，已被合成并充分表征。分离的复合物的动力学和化学能力在芳基苯基醚的合成中得到了证明，实验提供了反对涉及形成自由基或笼状自由基的机制途径的证据。
• A Radical and An Electron Transfer Process Are Compared in Their Regioselectivities Towards A Molecule with Two Different C−I Bonds: Effect of Steric Congestion
  作者：Barbara Branchi、Carlo Galli、Patrizia Gentili、Manuela Marinelli、Paolo Mencarelli

  DOI：10.1002/1099-0690(200007)2000:14<2663::aid-ejoc2663>3.0.co;2-y

  日期：2000.7

  bonding interaction of the hindered C−I bond of 2a. This causes a remarkable regioselectivity toward the weaker bond in dehalogenation by stannyl radicals. Conversely, a much lower regioselectivity is found for a process −a photostimulated SRN1 reaction with the enolate ion of a ketone − which requires the conversion of 2a into a radical anion. A calculation of the BDE of the C−I bond for aa ArI•− system

  1,4-二碘-2,6-二甲基苯 (2a) 中的空间压缩使甲基侧翼的 C-I 键比不受阻碍的 C-I 键弱得多（一种支撑效应）。计算还证实了 2a 的受阻 CI 键较弱的键合相互作用。这导致了对甲硅烷基自由基脱卤中较弱键的显着区域选择性。相反，发现一个过程的区域选择性要低得多 - 光刺激的 SRN1 反应与酮的烯醇离子 - 这需要将 2a 转化为自由基阴离子。提供了对 ArI•− 系统的 C−I 键的 BDE 计算。最后，由 2a•- 较弱的 C-I 键断裂产生的受阻芳基中间体在还原或取代之间显示出适度但可检测的区分，
• Composition of matter for use in organic light-emitting diodes
  申请人：Kyulux North America, Inc.

  公开号：US10892425B1

  公开（公告）日：2021-01-12

  The present disclosure relates to compounds of formula (I) or formula (II) as compounds capable of emitting delayed fluorescence and uses of these compounds in organic light-emitting diodes.

  本公开涉及公式(I)或公式(II)的化合物，这些化合物能够发出延迟荧光，并且在有机发光二极管中使用这些化合物。
• POLYMERIC COMPOUND AND LIGHT-EMITTING ELEMENT MANUFACTURED USING SAME
  申请人：Sumitomo Chemical Company Limited

  公开号：EP2980114A1

  公开（公告）日：2016-02-03

  A polymer compound comprising a constituent unit represented by the formula (1') and a constituent unit having a mono-valent cross-linkable group: [wherein R1' to R4' represent an alkyl group, an alkoxy group, an aryl group, an aryloxy group or a mono-valent heterocyclic group, R5 to R10 represent a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group or a mono-valent heterocyclic group, RA and RB represent a hydrogen atom, an alkyl group, an aryl group or a mono-valent heterocyclic group, and Ar1 and Ar2 represent an arylene group or a di-valent heterocyclic group.].

  一种聚合物化合物，包含由式（1'）表示的组成单元和具有单价可交联基团的组成单元： [其中 R1'至 R4'代表烷基、烷氧基、芳基、芳氧基或单价杂环基团，R5 至 R10 代表氢原子、烷基、烷氧基、芳基、芳氧基或单价杂环基团、RA 和 RB 代表氢原子、烷基、芳基或单价杂环基团，Ar1 和 Ar2 代表芳烯基团或二价杂环基团。].
• Mapping the mechanisms of oxidative addition in cross-coupling reactions catalysed by phosphine-ligated Ni(0)
  作者：Christina N. Pierson、John F. Hartwig

  DOI：10.1038/s41557-024-01451-x

  日期：——

  aryl halides to Ni(0) ligated by monophosphines occurs by both mechanisms and delineate how the branching of radical and non-radical pathways depends on the electronic properties of both the ligand and reactant arene as well as the identity of the halide. The one-electron pathway occurs by outer-sphere electron transfer to form an aryl radical rather than the often-proposed halogen atom transfer.

  第一行过渡金属的配合物可以通过多种途径进行基本反应，因为它们倾向于经历单电子和双电子氧化还原步骤。关于芳基卤化物与 Ni（0） 的氧化加成（广泛实践的交叉偶联过程中的常见步骤）的经典和最新研究得出了关于逐步、自由基与协同机制的相互矛盾的结论，但这些信息对于基于地球上丰富的金属的催化剂的设计至关重要。在这里，我们展示了芳基卤化物与单膦连接的 Ni（0） 的氧化加成是通过两种机制发生的，并描述了自由基和非自由基途径的分支如何取决于配体和反应物芳烃的电子性质以及卤化物的身份。单电子途径是通过外球电子转移形成芳基自由基而不是通常提出的卤素原子转移而发生的。