1-硝基-4-(1-辛炔)苯 | 326487-53-0

• 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-硝基-4-(1-辛炔)苯
• 英文名称: 1-(4-nitrophenyl)-1-octyne
• 英文别名: 1-nitro-4-(oct-1-yn-1-yl)benzene；1-Nitro-4-(oct-1-ynyl)benzene；1-nitro-4-oct-1-ynylbenzene
• CAS: 326487-53-0
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: CGOAGKYOZBGGJG-UHFFFAOYSA-N

物化性质

• 沸点：
  351.6±25.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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-硝基-4-(1-辛炔)苯 在 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、500.01 kPa 条件下， 反应 3.25h， 生成 tert-butyl 2-(4-octylphenylamino)acetate
  参考文献：
  名称：

  Fulleropyrrolidine End-Capped Molecular Wires for Molecular Electronics—Synthesis, Spectroscopic, Electrochemical, and Theoretical Characterization

  摘要：

  In continuation of previous studies showing promising metal molecule contact properties a variety of C-60 end-capped "molecular wires" for molecular electronics were prepared by variants of the Prato 1,3-dipolar cycloaddition reaction. Either benzene or fluorene was chosen as the central wire, and synthetic protocols for derivatives terminated with one or two fullero[c]pyrrolidine "electrode anchoring" groups were developed. An aryl-substituted aziridine could in some cases be employed directly as the azomethine ylide precursor for the Prato reaction without the need of having an electron-withdrawing ester group present. The effect of extending the pi-system of the central wire from 1,4-phenylenediamine to 2,7-fluorenediamine was investigated by absorption, fluorescence, and electrochemical methods. The central wire and the Co-60 end-groups were found not to electronically communicate in the ground state. However, the fluorescence of C60 was quenched by charge transfer from the wire to C-60. Quantum chemical calculations predict and explain the collapse of coherent electronic transmission through one of the fulleropyrrolidine-terminated molecular wires.

  DOI：

  10.1021/jo102066x
• 作为产物：
  描述：

  1-辛炔 、 对硝基氯苯 在 sodium tetrachloropalladate(II) copper(l) iodide 、 sodium carbonate 、 di(1-adamantyl)benzylphosphonium bromide 作用下， 以 甲苯 为溶剂， 反应 10.0h， 以93%的产率得到1-硝基-4-(1-辛炔)苯
  参考文献：
  名称：

  一种用于芳基氯的Sonogashira偶联的多功能催化剂。

  摘要：

  DOI：

  10.1002/anie.200390273

文献信息

• CHLORO-PYRAZINE CARBOXAMIDE DERIVATIVES WITH EPITHELIAL SODIUM CHANNEL BLOCKING ACTIVITY
  申请人：Parion Sciences, Inc.

  公开号：US20140171447A1

  公开（公告）日：2014-06-19

  This invention provides compounds of the formula I: and their pharmaceutically acceptable salts, useful as sodium channel blockers, compositions containing the same, therapeutic methods and uses for the same and processes for preparing the same.

  这项发明提供了式I的化合物及其药用盐，可用作钠通道阻滞剂，包含这些化合物的组合物，以及用于这些化合物的治疗方法和用途，以及制备这些化合物的方法。
• Ligand-, Copper-, and Amine-Free Sonogashira Reaction of Aryl Iodides and Bromides with Terminal Alkynes
  作者：Sameer Urgaonkar、John G. Verkade

  DOI：10.1021/jo049325e

  日期：2004.8.1

  and amine-free palladium-catalyzed Sonogashira reaction of aryl iodides and bromides with terminal alkynes have been developed. Critical to the success of this new protocol is the use of tetrabutylammonium acetate as the base. Noteworthy features of this method are room-temperature conditions and the tolerance of a broad range of functional groups in both reaction partners.

  已经开发出有效的无配体，无铜和无胺的钯催化的芳基碘化物和溴化物与末端炔烃的Sonogashira反应的条件。该新方案成功的关键是使用乙酸四丁铵作为碱。该方法的显着特征是室温条件和两个反应伙伴中多种官能团的耐受性。
• Copper- and phosphine-free Sonogashira coupling reactions of aryl iodides catalyzed by an N,N-bis(naphthylideneimino)diethylenetriamine-functionalized polystyrene resin supported Pd(II) complex under aerobic conditions
  作者：Mohammad Bakherad、Amir H. Amin、Ali Keivanloo、Bahram Bahramian、Mersad Raeissi

  DOI：10.1016/j.tetlet.2010.07.011

  日期：2010.10

  A polymer-supported palladium(II) N,N-bis(naphthylideneimino)diethylenetriamine complex is found to be a highly active catalyst for Sonogashira coupling reactions. The reactions are performed under copper- and phosphine-free conditions in an air atmosphere. The palladium catalyst is easily separated, and can be reused several times without significant loss in catalytic activity.

  发现聚合物负载的钯（II）N，N-双（萘二甲亚氨基）二亚乙基三胺络合物是用于Sonogashira偶联反应的高活性催化剂。反应在无铜和膦的条件下在空气气氛中进行。钯催化剂易于分离，并且可以重复使用几次而不会显着降低催化活性。
• γ-Valerolactone as an alternative biomass-derived medium for the Sonogashira reaction
  作者：Giacomo Strappaveccia、Lorenzo Luciani、Elena Bartollini、Assunta Marrocchi、Ferdinando Pizzo、Luigi Vaccaro

  DOI：10.1039/c4gc01728e

  日期：——

  γ-Valerolactone (GVL) can be used as an efficient and practical alternative to the banned and commonly used dipolar aprotic solvents. In this contribution GVL has been used as a non-toxic, biodegradable, biomass-derived medium, for the definition of a simple and general protocol for the Sonogashira cross-coupling reaction. The chemical efficiency of GVL as a medium is excellent and the best results

  γ-戊内酯（GVL）可以用作禁忌和常用的偶极非质子溶剂的有效替代品。在这一贡献中，GVL已被用作无毒，可生物降解的，生物质来源的培养基，用于定义Sonogashira交叉偶联反应的简单而通用的方案。GVL作为介质的化学效率极好，使用DABCO作为碱已获得了最佳结果，从而可以以60-96％的产率分离出3a-q产物。这些结果代表了一个实例，证明了生物质衍生的更安全的溶剂可以有效地用于常见的转化中，从而实现更高的绿色度/可持续性以及高化学效率。
• Aqueous Sonogashira coupling of aryl halides with 1-alkynes under mild conditions: use of surfactants in cross-coupling reactions
  作者：Gina M. Roberts、Wenya Lu、L. Keith Woo

  DOI：10.1039/c5ra00505a

  日期：——

  Aqueous Sonogashira coupling between lipophilic terminal alkynes and aryl bromides or iodides gave moderate to high yields at 40 °C using readily available and inexpensive surfactants (2.0 w/v% in water) such as SDS and CTAB. The catalyst precursor was 2 mol% Pd(PPh3)2Cl2, and included a 5 mol% Cu(I) co-catalyst for aryl iodide substrates. Aryl-bromide reagents were found to be inhibited by iodide

  亲脂性末端炔烃与芳基溴化物或碘化物之间的Sonogashira水溶液偶联在40°C下使用容易获得且便宜的表面活性剂（在水中为2.0 w / v％），例如SDS和CTAB，可得到中等至高收率。催化剂前体是2mol％的Pd（PPh 3）2 Cl 2，并且包括用于芳基碘化物底物的5mol％的Cu（I）助催化剂。发现芳基溴化物试剂被碘化物和Cu（I）抑制。在无Cu（I）条件下的研究揭示了两种竞争途径。去质子化途径产生了传统的Sonogashira产物（3），而碳pal化途径产生了烯炔[ 5]。。表面活性剂溶液（SDS或CTAB）最多可循环使用三次，以在CuI存在下在1-辛炔和1-碘庚烷之间偶联，然后降低产率。