1,2-二丁基-4,5-二碘苯 | 744245-77-0

• 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: 1,2-二丁基-4,5-二碘苯
• 英文名称: 4,5-dibutyl-1,2-diiodobenzene
• 英文别名: 1,2-dibutyl-4,5-diiodobenzene
• CAS: 744245-77-0
• 化学式: C₁₄H₂₀I₂
• 分子量: 442.122
• InChiKey: CRYFHROMGKXYBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  1,2-二丁基-4,5-二碘苯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 4.5h， 生成 4.5-dibutyl-2-trimethylsilylethynylbenzaldehyde
  参考文献：
  名称：

  Synthesis and Properties of a Tricyclic Hexaketone Monohydrate with Hexabutyl Side Chain

  摘要：

  DOI：

  10.3987/com-18-s(f)85
• 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 1,2-二丁基-4,5-二碘苯
  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

• Copper-Mediated Simple and Efficient Synthesis of Tribenzohexadehydro[12]annulene and Its Derivatives
  作者：Masahiko Iyoda、Siriwan Sirinintasak、Yoshihiro Nishiyama、Anusorn Vorasingha、Fatema Sultana、Kazumi Nakao、Yoshiyuki Kuwatani、Haruo Matsuyama、Masato Yoshida、Yoshihiro Miyake

  DOI：10.1055/s-2004-822393

  日期：——

  A simple and efficient synthesis of tribenzohexadehydro[12]annulene and its derivatives was carried out using coupling reaction of acetylenes with iodoarenes in the presence of catalytic amounts of CuI and PPh,, together with three equivalents of K 2 CO 3 in DMF. This synthetic procedure was applied to the synthesis of a large annulenoannulene derivative.

  在催化量的 CuI 和 PPh 以及三当量的 DMF 中的 K 2 CO 3 存在下，使用乙炔与碘代芳烃的偶联反应进行了三苯并六氢[12]环烯及其衍生物的简单有效合成。该合成程序适用于合成大环烯基环烯衍生物。
• Synthesis of pentadecaphenylenes, their inclusion properties, and nanostructure formation with C60
  作者：M. Jalilur Rahman、Hideyuki Shimizu、Yasuyuki Araki、Hiroshi Ikeda、Masahiko Iyoda

  DOI：10.1039/c3cc42922a

  日期：——

  Synthesis of macrocyclic pentadecaphenylene was carried out via electron-transfer oxidation of the corresponding Lipshutz cuprate. Pentadecaphenylene self-aggregated in solution to form a gel. Furthermore, it incorporated C60 in its cavity to produce a fibrous inclusion complex which showed a high gelation ability in benzene.

  通过相应的立普舒兹铜酸盐的电子转移氧化作用，合成了大环十五碳苯。十五碳苯在溶液中自我聚集形成凝胶。此外，它还在其空腔中加入了 C60，产生了一种纤维状包合物，在苯中显示出很强的凝胶能力。
• Synthesis of Nonaphenylenes and Dodecaphenylenes Using Electron-transfer Oxidation of Lipshutz Cuprate Intermediates
  作者：Masahiko Iyoda、Mohammad Jalilur Rahman、Aoi Matsumoto、Mo Wu、Yoshiyuki Kuwatani、Kazumi Nakao、Yoshihiro Miyake

  DOI：10.1246/cl.2005.1474

  日期：2005.11

  Nonaphenylene and its hexaalkyl derivatives have been synthesized using electron-transfer oxidation of Lipshutz cuprates with duroquinone. Oxidation of the Lipshutz cuprate derived from dibromo-o-terphenyl in THF produced nonaphenylene in moderate yield, whereas the similar oxidation of the Lipshutz cuprate derived from diiododiethyl-o-terphenyl in ether afforded the corresponding nonaphenylene and dodecaphenylene. Furthermore, oxidation of Lipshutz cuprate derived from diiododibutyl-o-terphenyl only gave the nonaphenylene.

  利用电子转移氧化法合成了壬基苯及其六烷基衍生物。在四氢呋喃中氧化由二溴邻三联苯衍生的利普舒茨铜酸盐，可生成九亚苯基，收率适中；而在乙醚中氧化由二碘二乙基邻三联苯衍生的利普舒茨铜酸盐，可生成相应的九亚苯基和十二亚苯基。此外，由二碘二丁基邻三联苯衍生的 Lipshutz 铜酸盐氧化反应只能得到壬烯。
• Synthesis of Nonaphenylenes and Dodecaphenylenes Using Electron-Transfer Oxidation of Lipshutz Cuprates and Formation of Nanostructural Materials from Hexadodecyloxynonaphenylene
  作者：M. Jalilur Rahman、Jun Yamakawa、Aoi Matsumoto、Hideo Enozawa、Tohru Nishinaga、Kenji Kamada、Masahiko Iyoda

  DOI：10.1021/jo800787u

  日期：2008.7.1

  Nonaphenylenes and dodecaphenylenes have been synthesized by using electron-transfer oxidation of Lipshutz cuprates with duroquinone. Oxidation of the Lipshutz cuprate derived from 4,4"-dibromo-o-terphenyl 3a in THF produced nonaphenylene la in 46% yield, whereas the similar oxidation of the Lipshutz cuprates derived from 4,4"-diiodo-4',5'-dialkyl-o-terphenyls 3b-d in ether afforded the corresponding nonaphenylenes 1b-d and dodecaphenylenes. 2b-d in moderate total yields. In the case of 4,4"-diiodo-4',5'-didodecyloxy-o-terphenyl 3e as the starting material, oxidation of the corresponding Lipshutz cuprate in ether or THF only led to the formation of nonaphenylene le. Both nonaphenylenes 1a-e and dodecaphenylenes 2b-d are unreactive to fight, atmospheric oxygen, and prolonged heating. These oligophenylenes showed strong UV absorption and fluorescent emission and exhibited some redox properties on CV analysis. Moreover, hexadodecyloxyrionaphenylene le exhibits different nanostructures on the surface and in solution to form a film by casting a solution of 1e in cyclohexane, benzene, chloroform, THF, or diisopropyl ether (EPE) and nanofibers from IPE-MeOH (1: 1), indicating different absorption and emission spectra and XRD patterns. The absorption maxima of THF solution, fiber, and film are in the order of le film (315 nm) > fiber (302 nm) > solution (295 ran), whereas the emission maxima are in the order of 1e fiber (425 m) > solution (418 nm) > film (401 nm). XRD analysis revealed that le aligns laterally on a glass or silicon surface to form a thin film with a lamella structure; however, it forms a nanofiber with a Lego-like stacking structure without pi-pi stacking interaction of the aromatic rings. Reflecting the different nanostructures of the 1e film and fiber, a spin-coated le film is found to be effective in detecting the vapor of explosives due to the intercalation of nitroaromatics to the cracked surface of the loosely stacked 1e. In contrast, the 1e fiber is not effective in detection of nitroaromatics but exhibits fluorescence anisotropy. The maximum fluorescence intensity is obtained in a direction perpendicular to the logitudinal axis of the fiber, indicating the stacking direction to be parallel to the longitudinal axis of the fiber.
• Donor–Acceptor Segregated Paracyclophanes Composed of Naphthobipyrrole and Stacked Fluoroarenes
  作者：Masayoshi Takase、Ayumi Inabe、Yuki Sugawara、Wataru Fujita、Tohru Nishinaga、Kotohiro Nomura

  DOI：10.1021/ol400882q

  日期：2013.7.5

  The expeditious synthesis of donor-acceptor segregated paracyclophanes has been achieved by a selective SNAr reaction of hexafluorobenzene with o-dipyrrolylbenzenes and subsequent cyclodehydrogenation. An orthogonally arranged D-A segregated structure was confirmed by X-ray crystallography. The combined results of DFT calculations and absorption spectra revealed the charge transfer (CT) nature from the naphthobipyrrole (donor) to the stacked fluoroarene moiety (acceptor).