1,2-dihexyl-4,5-diiodobenzene | 155259-26-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,2-dihexyl-4,5-diiodobenzene
• 英文别名: 4,5-dihexyl-1,2-diiodobenzene
• CAS: 155259-26-0
• 化学式: C₁₈H₂₈I₂
• 分子量: 498.229
• InChiKey: NGKQUWFTHLBHSL-UHFFFAOYSA-N

物化性质

• 沸点：
  419.2±45.0 °C(Predicted)
• 密度：
  1.503±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,2-dihexyl-4,5-diiodobenzene 在 bis-triphenylphosphine-palladium(II) chloride 氢氧化钾 、 copper(l) iodide 、 四甲基乙二胺 、 氧气 、 二异丙胺 、 copper(l) chloride 作用下， 以 四氢呋喃 、 甲醇 、 邻二氯苯 为溶剂， 反应 0.5h， 生成 2,2'-diethynyl-4,4',5,5'-tetrahexyldiphenyldiacetylene
  参考文献：
  名称：

  Synthesis of Diacetylene Macrocycles Derived from 1,2-Diethynyl Benzene Derivatives: Structure and Reactivity of the Strained Cyclic Dimer

  摘要：

  Diacetylene macrocycles 2-4 (n = 1-3) (R = H, C4H9, C6H13, C10H21, C12H25, OC10H21) have been prepared from the oxidative coupling of 1,2-diethynylbenzene derivatives. These compounds can be produced in useful quantities and are of interest as precursors to novel conjugated organic polymers. The reported results indicate that when the R groups are large the dimeric macrocycle (n = 1) can be prepared in as high as 74% yield from the corresponding 1,2-diethynylbenzene in a one-step procedure. An alternate multistep procedure was found to produce the tetrameric macrocycle (n = 3, R = C6H13) in 45 % yield. The highly strained dimeric macrocycle was characterized by an X-ray structure and was found to be very reactive. The dimers undergo a rapid very exothermic polymerization at 100-125-degrees-C, indicative of a chain reaction. Reaction of the dimeric macrocycles with iodine results in intramolecular cyclization and a new 20pi electron tetraiodide fused ring system. Reaction of the tetraiodide with oxygen produces a related compound in which two of the iodides have been converted to ketones.

  DOI：

  10.1021/jo00085a016
• 作为产物：
  描述：

  邻二氯苯 在 bis(triphenylphosphine)nickel(II) chloride sodium iodate 、 硫酸 、 碘 、 magnesium 作用下， 以 溶剂黄146 为溶剂， 反应 1.5h， 生成 1,2-dihexyl-4,5-diiodobenzene
  参考文献：
  名称：

  Synthesis of Diacetylene Macrocycles Derived from 1,2-Diethynyl Benzene Derivatives: Structure and Reactivity of the Strained Cyclic Dimer

  摘要：

  Diacetylene macrocycles 2-4 (n = 1-3) (R = H, C4H9, C6H13, C10H21, C12H25, OC10H21) have been prepared from the oxidative coupling of 1,2-diethynylbenzene derivatives. These compounds can be produced in useful quantities and are of interest as precursors to novel conjugated organic polymers. The reported results indicate that when the R groups are large the dimeric macrocycle (n = 1) can be prepared in as high as 74% yield from the corresponding 1,2-diethynylbenzene in a one-step procedure. An alternate multistep procedure was found to produce the tetrameric macrocycle (n = 3, R = C6H13) in 45 % yield. The highly strained dimeric macrocycle was characterized by an X-ray structure and was found to be very reactive. The dimers undergo a rapid very exothermic polymerization at 100-125-degrees-C, indicative of a chain reaction. Reaction of the dimeric macrocycles with iodine results in intramolecular cyclization and a new 20pi electron tetraiodide fused ring system. Reaction of the tetraiodide with oxygen produces a related compound in which two of the iodides have been converted to ketones.

  DOI：

  10.1021/jo00085a016

文献信息

• Improved Access to 1,8-Dichloro-10-(ethynyl)anthracene: A Useful Building Block for (Semi-)rigid Organic Frameworks
  作者：Jan-Hendrik Lamm、Philipp Niermeier、Leif Körte、Beate Neumann、Hans-Georg Stammler、Norbert Mitzel

  DOI：10.1055/s-0036-1591925

  日期：2018.5

  a substrate in (cross-)coupling reactions and some examples of linked 1,8-dichloroanthracen-10-yls (e.g., 1,8-bis[(1,8-dichloroanthracen-10-yl)-ethynyl]naphthalene or 1,2-bis[(1,8-dichloroanthracen-10-yl)ethynyl]-benzene) were synthesized in good to moderate yields. Linked 1,8-dichloroanthracen-10-yl derivatives were also synthesized by cross-coupling reactions using 10-bromo-1,8-dichloroanthracene

  ‡这些作者对这项工作做出了同等的贡献。 抽象的 据报道，很容易获得1,8-二氯-10-（乙炔基）蒽，它广泛适用于在两个1,8-二氯蒽单元之间建立刚性连接基。为此，在CeCl 3存在下，使1,8-二氯蒽-10（9 H）-1与乙炔基溴化镁反应; 产率为65％。该结构单元用作（交叉）偶联反应和（例如）1,8-双[（1,8-dichloroanthracen-10-yl）-合成乙炔基萘或1,2-双[（1,8-二氯蒽-10-基）乙炔基]-苯）的产率中等至中等。还使用10-溴-1,8-二氯蒽和双乙炔基取代的底物通过交叉偶联反应合成了连接的1,8-二氯蒽-10-基团衍生物。1,8-二氯蒽单元之间的连接基为：丁二炔二基，二甲基甲硅烷基二乙炔基，辛基1,8,7-二炔-1,8-二基，丙烷-1,3-二基双（二甲基甲硅烷基）二乙炔基，苯1,2-二乙炔基，萘-1，8-二基二乙炔基和蒽-1，8-二基二乙炔基。通过NM
• Redox-switchable Intramolecular<i>π−π</i>-Stacking of Perylene Bisimide Dyes in a Cyclophane
  作者：Felix Schlosser、Michael Moos、Christoph Lambert、Frank Würthner

  DOI：10.1002/adma.201201266

  日期：2013.1.18

  Molecular actuation by stepwise electrochemical reduction is demonstrated for a cyclophane that exhibits a pronounced conformational transition from a closed cavity with cofacially stacked PBIs in the neutral state to an expanded open cavity in the three‐ and fourfold reduced state.

  已证明，通过逐步电化学还原的分子致动环烯具有明显的构象过渡，该闭合构象从具有中性状态的界面堆叠的PBI的封闭腔到三倍和四倍还原态的扩展开腔。
• Synthesis of a Trinuclear Tropolone–Palladium(II) Macrocycle and Its C₆₀ Inclusion Properties
  作者：Hiroyuki Otani、Chisaki Sumi、Hideyuki Shimizu、Masashi Hasegawa、Masahiko Iyoda

  DOI：10.1246/cl.140638

  日期：2014.11.5

  4,5-Dialkyl-1,2-bis(5-tropolonylethynyl)benzenes 5a and 5b were synthesized, and dioctyl derivative 5a was converted into the corresponding trinuclear palladium(II) macrocycle 1a by reacting it with Pd(OAc)2. Macrocyclic supramolecular coordination complex 1a has an inner cavity just large enough to include C60. Although trinuclear palladium complex 1a incompletely incorporated C60 in solution owing to weak interactions between the bis(tropolono)palladium(II) moieties and C60, it formed an inclusion complex with C60 in the solid state. The inclusion complex showed a moderate charge-transfer absorption in the UV–vis–NIR spectra.

  合成了4,5-二烷基-1,2-双(5-环丙炔基乙炔基)苯5a和5b，二辛基衍生物5a通过与Pd(OAc)2反应转化为相应的三核钯(II)大环1a。大环超分子配位络合物1a的内腔刚好足以容纳C60。尽管三核钯配合物1a由于双(托波罗)钯(II)部分与C60之间的弱相互作用而在溶液中不完全结合C60，但它在固态下与C60形成了包合物。包合物在紫外-可见-近红外光谱中显示出中等的电荷转移吸收。
• Phenylene Ethynylene-Tethered Perylene Bisimide Folda-Dimer and Folda-Trimer: Investigations on Folding Features in Ground and Excited States
  作者：Benjamin Fimmel、Minjung Son、Young Mo Sung、Matthias Grüne、Bernd Engels、Dongho Kim、Frank Würthner

  DOI：10.1002/chem.201405231

  日期：2015.1.7

  been studied by solvent‐dependent UV/Vis absorption and 1D and 2D NMR spectroscopy, revealing facile folding of both systems in tetrahydrofuran (THF). In CHCl3 the dimer exists in extended (unfolded) conformation, whereas partially folded conformations are observed in the trimer. Temperature‐dependent 1H NMR spectroscopic studies in [D8]THF revealed intramolecular dynamic processes for both PBI foldamers

  在这项工作中，我们已经详细说明了两个分别由两个和三个PBI单元组成的二per双酰亚胺（PBI）折叠剂的折叠特性，它们分别连接到亚苯基亚乙炔主链上。这些新的PBI折叠二聚体和三聚体的折叠行为已通过溶剂依赖性的UV / Vis吸收以及1D和2D NMR光谱进行了研究，揭示了这两个系统在四氢呋喃（THF）中的容易折叠。在CHCl 3中，二聚体以延伸（未折叠）构象存在，而在三聚体中观察到部分折叠的构象。温度依赖性1周1 H NMR光谱中的研究[d 8 ] THF揭示由于分子内的动态过程两者PBI foldamers，在一方面，受阻围绕Ç旋转N个酰亚胺键，另一方面，主链拍打；由于仅在升高的温度下才观察到，后一种方法的能量要求更高。[D 8]中的不同2D-NMR光谱（例如ROESY和DOSY）已经阐明了二聚体和三聚体的折叠构象的结构特征。]四氢呋喃。PBI二聚体和三聚体的折叠过程的能量已经通过应用各
• Accessing Indenoazulenes <i>via</i> a Gold‐Catalysed Cyclisation of Cycloheptatrienyl‐Substituted 1,5‐Diynes
  作者：Alexandra V. Mackenroth、Alexander Ahrens、Jonas F. Wunsch、Raphael Berger、Frank Rominger、Matthias Rudolph、A. Stephen K. Hashmi

  DOI：10.1002/adsc.202301037

  日期：2024.3.19

  Plattner and Pfau,14 as well as the noteworthy access to azulenes developed in 1955 by Ziegler and Hafner,15 were followed by various other synthetic approaches.16 However, to date it still remains challenging to access azulenes with specific substitution patterns and functionalities, which necessitates the development of further complementary synthetic strategies. In the recent years, several transition

  介绍 在过去的几年中，1,5-二炔已成为金催化环化的非常有价值的合成支架，为有趣的芳香系统提供了机会。1根据炔烃单元上的主链和取代基，这些二炔可以进行 5-内位环化或 6-内位环化。2最初，重点放在具有至少一个末端炔烃单元的系统上，该系统可以通过双金催化激活，其中涉及 σ 配位的金乙炔化物对 π 配位的第二个炔烃的攻击。3对于 5- end - dig环化的情况，这会导致金亚乙烯基的形成，这些亚乙烯基可以被 CH 插入捕获，例如产生苯并富烯2a、4或二苯并五烯5子结构（方案 1）。随后开发的方法能够激活非末端二炔。芳基取代的 1,5-二炔被证明可以通过单金活化产生芳基化二苯并戊二烯，涉及形成芳基稳定的乙烯基阳离子（方案 1）。6这开启了访问许多潜在有趣结构的可能性，特别是在材料科学方面。7在此，我们设想用环庚三烯基取代基代替炔烃上的芳基，可能能够合成 11 H -茚并-[2,1- a ]薁