1,2-二癸基-4,5-二碘苯 | 191231-92-2

• 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: 1,2-二癸基-4,5-二碘苯
• 英文名称: 1,2-didecyl-4,5-diiodobenzene
• CAS: 191231-92-2
• 化学式: C₂₆H₄₄I₂
• 分子量: 610.444
• InChiKey: ZJFWXVDZAOGFNN-UHFFFAOYSA-N

物化性质

• 沸点：
  522.5±50.0 °C(Predicted)
• 密度：
  1.317±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  13.5
• 重原子数：
  28
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 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：

  1,2-二癸基-4,5-二碘苯 在 bis-triphenylphosphine-palladium(II) chloride 、 四(三苯基膦)钯 甲醇 、 copper(l) iodide 、 potassium carbonate 、 二异丙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Carbon Networks Based on Benzocyclynes. 6. Synthesis of Graphyne Substructures via Directed Alkyne Metathesis

  摘要：

  Intramolecular ring closing alkyne metathesis afforded the graphyne biscyclyne (3) in high macrocyclization yield and good overall yield. This methodology also furnished the tris[12]cyclyne 4, which contains the longest linear diphenylacetylene conjugation pathway for any graphyne substructure based on the tribenzo[12]cyclyne core.

  DOI：

  10.1021/ol7014253
• 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 硫酸 、 溶剂黄146 为溶剂， 反应 1.5h， 生成 1,2-二癸基-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

• Stepwise Assembly of Site Specifically Functionalized Dehydrobenzo[18]annulenes
  作者：Joshua J. Pak、Timothy J. R. Weakley、Michael M. Haley

  DOI：10.1021/ja991749g

  日期：1999.9.1

  Site specifically functionalized dehydrobenzo[18]annulenes (DBAs) with previously inaccessible topologies (C2v and Cs symmetry) were prepared by utilizing an in situ protiodesilylation/alkynylation reaction. By application of a stepwise synthetic route, donor and/or acceptor functional groups were introduced to the annulenic core in a designed manner. The electronic absorption spectra of the DBAs revealed

  通过利用原位蛋白脱甲硅烷基化/炔化反应制备了具有以前无法获得的拓扑结构（C2v 和 Cs 对称性）的位点特异性功能化脱氢苯并 [18] 环烯 (DBA)。通过应用逐步合成路线，以设计的方式将供体和/或受体官能团引入到环核中。DBA 的电子吸收光谱显示，当取代模式和/或官能团发生细微变化时，[18] 轮烯核的电子结构发生了中度至剧烈的变化。包含 C2v 对称性的大环表现出从 20 到 80 nm 的渐进和可预测的红移，以及增加的分子内激发态变化转移 (CT) 行为。不对称（Cs）分子呈现出更有趣的吸收行为，例如可见区域中带的加重。[18]DBA 20、22、23 和 25 的 X 射线晶体结构在平面环内显示出正常的键长和键角。
• Synthesis and photophysical properties of expanded dehydrobenzoannulene macrotricycles
  作者：Takashi Takeda、Michael M. Haley

  DOI：10.1139/cjc-2016-0430

  日期：2017.3

  A sequential Sonogashira cross-coupling/Pd-mediated oxidative homocoupling strategy affords two expanded dehydrobenzoannulene (DBA) structures containing two [14]DBAs fused to an [18]DBA core. Noticeable differences in the absorption and emission spectra are observed in comparison with a structurally related [18]DBA-centered trefoil containing three fused [14]DBAs.

  一种顺序Sonogashira交叉偶联/Pd催化氧化自偶联策略可制备出两种扩展的去氢苯并环戊烯（DBA）结构，其中包含两个[14]DBA融合到一个[18]DBA核心中。与一个结构相关的[18]DBA中心三叶草形式包含三个融合的[14]DBA相比，吸收和发射光谱中观察到明显的差异。
• Carbon Networks Based on Dehydrobenzoannulenes. 5. Extension of Two-Dimensional Conjugation in Graphdiyne Nanoarchitectures
  作者：Jeremiah A. Marsden、Michael M. Haley

  DOI：10.1021/jo050926v

  日期：2005.12.1

  The synthesis and optical properties of a series of multinanometer-sized substructures of the phenyl-diacetylene carbon allotrope, graphdiyne, are described. These molecules are among the largest and most complex annulenic systems yet prepared, with extension of linear conjugation in two-dimensions to over twice that of any previously reported planar macrocycle. The graphdiyne substructures are constructed through convergent syntheses, taking advantage of three key intermediates and silane-protected phenylacetylenes. Intramolecular macrocyclization of alpha,omega-polyyne precursors via Cu-niediated or Pd-catalyzed oxidative homocoupling affords five new graphdiyne "oligomers" possessing two to flour fused 1.8-membered rings. The attempted synthesis of a six-ring analogue is also reported.
• Haley, Michael M.; Brand, Stephen C.; Pak, Joshua J., Angewandte Chemie - International Edition in English, 1997, vol. 36, # 8, p. 835 - 838
  作者：Haley, Michael M.、Brand, Stephen C.、Pak, Joshua J.

  DOI：——

  日期：——
• Zhou Qin, Carroll Patrick J., Swager Timothy M., J. Org. Chem., 59 (1994) N 6, S 1294-1301
  作者：Zhou Qin, Carroll Patrick J., Swager Timothy M.

  DOI：——

  日期：——