1,4-二乙炔基-2-硝基苯 | 113639-27-3

• 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: 1,4-二乙炔基-2-硝基苯
• 英文名称: 1,4-diethynyl-2-nitrobenzene
• 英文别名: 1-nitro-2,5-diethynylbenzene；2-nitro-1,4-diethynylbenzene
• CAS: 113639-27-3
• 化学式: C₁₀H₅NO₂
• 分子量: 171.155
• InChiKey: CWBMRLUVZIIYHK-UHFFFAOYSA-N

物化性质

• 熔点：
  127-128 °C(Solv: ethanol (64-17-5))
• 沸点：
  269.4±35.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4-二乙炔基-2-硝基苯 在 ammonium hydroxide 、 sodium hydride 、 copper(l) chloride 、 锌 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 19.0h， 生成 2-morpholinomethyl-6-(3-morpholinoprop-1-ynyl)indole
  参考文献：
  名称：

  Synthesis and transformations of 1,4-diethynyl-2-nitrobenzene

  摘要：

  用POCl3加热2-硝基-1,4-双(1,3,3-三甲基吲哚啉-2-亚基乙酰)苯，然后用NaOH水溶液处理，得到2-硝基-1,4-二乙炔苯。考虑了涉及该产品的某些转化。2-乙酰氨基-1,4-二乙炔苯及其二吗啉甲基衍生物发生杂环化反应，生成末端和甲烷碳取代的吲哚乙炔。

  DOI：

  10.1007/s11172-006-0160-z
• 作为产物：
  描述：

  2,5-二溴硝基苯 在 甲醇 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 1,4-二乙炔基-2-硝基苯
  参考文献：
  名称：

  作为潜在电子器件的大环分子棒的合成

  摘要：

  报道了大环 1 和 2 作为模型化合物的设计和合成，用于研究分子连接中的负微分电导现象。大环 1 和 2 包含由三个乙炔基连接的苯环组成的分子棒亚基。虽然两个末端苯环沿杆轴的旋转自由度受到大环框架的限制，但中心苯环是旋转的。棒子结构末端用乙酰基保护的硫醇基团官能化，以使其固定在金触点之间。中心苯环分别用一个和两个硝基官能化，分别代表 1 和 2。硝基特别重要，因为 i) 两个大环都是模型化合物，用于研究硝基与相反大环亚基的假设分子内相互作用，以及 ii) 硝基导致化合物的热稳定性有限，因为分子内重排为包含 isatogen 亚基的大环化合物。这些高度官能化的大环化合物是通过乙炔支架策略结合官能团转化化学组装而成的。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

  DOI：

  10.1002/ejoc.200600336

文献信息

• Carbodithioate-Terminated Oligo(phenyleneethynylene)s:  Synthesis and Surface Functionalization of Gold Nanoparticles
  作者：Tae-Hong Park、Michael J. Therien

  DOI：10.1021/ol070789j

  日期：2007.7.1

  Carbodithioate-terminated bis(phenylene)ethynylenes and oligo(phenyleneethynylene)s have been synthesized from TMSE-protected 4-iododithiobenzoic acid ester (1) and 4-ethynyldithiobenzoic acid ester (3) via Pd-catalyzed cross-coupling reactions. TEM and spectroscopic studies demonstrate that the reaction of 4-(phenylethynyl)dithiobenzoate with alkylamine-protected gold nanoparticles (AuNPs) produces the corresponding organocarbodithioate-functionalized AuNPs.
• Acetylenic fragmentation of acyl derivatives of the Fischer base
  作者：N. M. Prizhiyalgovskaya、L. I. Kon'kov、D. L. Tarshits、S. V. Salmina、N. T. Segizova、N. N. Suvorov

  DOI：10.1007/bf00475641

  日期：1987.7
• Improved and new syntheses of potential molecular electronics devices
  作者：David W Price、Shawn M Dirk、Francisco Maya、James M Tour

  DOI：10.1016/s0040-4020(03)00246-1

  日期：2003.3

  New syntheses of ethyl and nitro substituted oligo(phenylene ethynylene)s (OPEs) have been developed. To further explore whether the presence of nitro functionality in OPEs leads to switching and memory capabilities, new nitro substituted OPEs have been designed and synthesized. An isatogen-based system, a structure that is isomeric to the nitro OPE, has been synthesized. Additionally, pyridine-based and chromium-based compounds have been synthesized. We surmise that redox reactions of these candidates may impart switching capabilities and electrochemical studies are shown. U-shaped OPEs were synthesized to inhibit leakage of metals deposited during formation of top contacts on self-assembled monolayers (SAMs). The OPEs contain either thiol-based moieties or isonitrile groups to enable formation of SAMs on metal substrates. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Synthesis, Characterization, and Substituent Effects of Binuclear Ruthenium Vinyl Complexes [RuCl(CO)(PMe₃)₃]₂(μ-CH═CH−Ar−CH═CH)
  作者：Xiang Hua Wu、Shan Jin、Jin Hua Liang、Zi Yong Li、Guang-ao Yu、Sheng Hua Liu

  DOI：10.1021/om900018y

  日期：2009.4.27

  A series of binuclear ruthenium vinyl complexes [RuCl(CO)(PMe3)(3)](2)(mu-CH=CH-Ar-CH=CH) (Ar = C6H4 (6a), C6H3CH3 (6b), C6H3OCH3 (6c), C6H3F (6d), C6H3Cl (6e), C6H3Br (6f), C6H3CN (6g), C6H3NO2 (6h), C6H2(CH3)(2)-2,5 (6i), C6H2(OCH3)(2)-2,5 (6i), C6H2(F)(2)-2,5 (6k), C6H2(CF3)(2)-2,5 (6l), and C6H3CF3 (6m)) have been prepared. The respective products have been characterized by elemental analyses, NMR spectrometry, and UV/vis spectrophotometry. The structures of 6h, 6i, and 6j have been established by X-ray crystallography. Electrochemical studies have revealed that intermetallic electron communication between the two Ru centers may be fine-tuned by modification of the bridging spacers, that is, by introducing one or two substituent groups on the 1,4-diethenylphenylene bridge. Electron-releasing substituents have been found to facilitate electron communication between the two metal centers.
• Scanning Tunneling Microscopy of Self-Assembled Phenylene Ethynylene Oligomers on Au(111) Substrates
  作者：Karsten Walzer、Eike Marx、Neil C. Greenham、Robert J. Less、Paul R. Raithby、Kurt Stokbro

  DOI：10.1021/ja036771v

  日期：2004.2.1

  In this paper, we report the self-assembly, electrical characterization, and surface modification of dithiolated phenylene-ethynylene oligomer monolayers on a Au(111) surface. The self-assembly was accomplished by thiol bonding the molecules from solution to a Au(111) surface. We have confirmed the formation of self-assembled monolayers by scanning tunneling microscopy (STM) and optical ellipsometry, and have studied the kinetics of film growth. We suggest that self-assembled phenylene ethynylene oligomers on Au(111) surfaces grow as thiols rather than as thiolates. Using low-temperature STM, we collected local current-voltage spectra showing negative differential resistance at 6 K.