5-碘喹啉-8-胺 | 142340-15-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 5-碘喹啉-8-胺
• 英文名称: 5-iodoquinolin-8-amine
• 英文别名: 5-iodo-8-aminoquinoline；5-Iodoquinolin-8-amine
• CAS: 142340-15-6
• 化学式: C₉H₇IN₂
• 分子量: 270.072
• InChiKey: UJCDMYCTCVPZME-UHFFFAOYSA-N

物化性质

• 熔点：
  123.1-124.5 °C
• 沸点：
  388.6±32.0 °C(Predicted)
• 密度：
  1.913±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.9
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  5-碘喹啉-8-胺 在 甲醇 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 三乙胺 、 N,N-二异丙基乙胺 、 potassium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 32.0h， 生成 DAQZ
  参考文献：
  名称：

  A ratiometric fluorescent probe for oxalate based on alkyne-conjugated carboxamidoquinolines in aqueous solution and imaging in living cells

  摘要：

  一种新型比率荧光探针被设计和合成，基于锌含量的[DAQZ@2Zn2+]复合物。它在水溶液中对草酸显示出高度选择性的“开启-关闭”荧光变化，波长蓝移超过20 nm。此外，它可以在活细胞中荧光响应草酸。

  DOI：

  10.1039/c0dt01364a
• 作为产物：
  描述：

  5-碘喹啉 在 硫酸 、 硝酸 作用下， 生成 5-碘喹啉-8-胺
  参考文献：
  名称：

  Howitz; Fraenkel; Schroeder, Justus Liebigs Annalen der Chemie, 1913, vol. 396, p. 63

  摘要：

  DOI：

文献信息

• Halogen Bond-Assisted Electron-Catalyzed Atom Economic Iodination of Heteroarenes at Room Temperature
  作者：Imran Kazi、Somraj Guha、Govindasamy Sekar

  DOI：10.1021/acs.joc.9b00174

  日期：2019.6.7

  halogen bond-assisted electron-catalyzed iodination of heteroarenes has been developed for the first time under atom economic condition at room temperature. The iodination is successful with just 0.55 equiv of iodine and 0.50 equiv of peroxide. The kinetic study indicates that the reaction is elusive in the absence of a halogen bond between the substrate and iodine. The formation of a halogen bond, its

  在室温下原子经济条件下，首次开发了卤素键辅助的电子催化的杂芳烃碘化反应。仅用0.55当量的碘和0.50当量的过氧化物就能成功进行碘化。动力学研究表明，在底物和碘之间不存在卤素键的情况下，该反应难以捉摸。卤素键的形成，其在降低该反应的活化势垒中的重要性，反应混合物中自由基中间体的存在以及反应的区域选择性已通过数个对照实验，光谱分析和量子化学计算得到了证明。
• Enantioselective Alkylamination of Unactivated Alkenes under Copper Catalysis
  作者：Zibo Bai、Heng Zhang、Hao Wang、Hanrui Yu、Gong Chen、Gang He

  DOI：10.1021/jacs.0c12333

  日期：2021.1.20

  An enantioselective addition reaction of various alkyl groups to unactivated internal alkenes under Cu catalysis has been developed. The reaction uses amide-linked aminoquinoline as the directing group, 4-alkyl Hantzsch esters as the donor of alkyl radicals, and rarely used biaryl diphosphine oxide as a chiral ligand. β-lactams featuring two contiguous stereocenters at Cβ and the β substituent can

  已经开发了在铜催化下各种烷基与未活化的内烯烃的对映选择性加成反应。该反应使用酰胺连接的氨基喹啉作为导向基团，4-烷基汉茨酯作为烷基的供体，很少使用联芳基二氧化膦作为手性配体。β-内酰胺在 Cβ 和 β 取代基上具有两个连续的立体中心，可以以良好的收率和优异的对映选择性获得。机理研究表明，烷基自由基与 CuII 配位烯烃的亲核加成是对映体决定步骤。
• β-Lactam Synthesis via Copper-Catalyzed Directed Aminoalkylation of Unactivated Alkenes with Cyclobutanone <i>O</i>-Benzoyloximes
  作者：Heng Zhang、Xiaoyan Lv、Hanrui Yu、Zibo Bai、Gong Chen、Gang He

  DOI：10.1021/acs.orglett.1c01007

  日期：2021.5.7

  amide-directed Cu-catalyzed aminoalkylation of unactivated alkenes using cyclobutanone oxime esters as alkyl radical donors is developed. Both primary and secondary alkyl groups can be selectively installed at the C4 position of terminal or cis-internal 3-alkenamides in moderate to good yield. This reaction offers a useful method for the diastereoselective synthesis of β-lactams bearing 4-cyanoalkyl β-substituents

  开发了一种新的协议，用于使用环丁酮肟酯作为烷基供体的未活化烯烃的酰胺定向铜催化的氨基烷基化。伯烷基和仲烷基都可以以中等至良好的产率选择性地安装在末端或顺式-内部3-烯酰胺的C4位置。该反应提供了用于非对映选择性合成带有4-氰基烷基β-取代基的β-内酰胺的有用方法。使用弱配位的抗衡阴离子作为Cu催化剂对于形成β-内酰胺产品至关重要。
• Nickel(II)-Mediated Regioselective CH Monoiodination of Arenes and Heteroarenes by using Molecular Iodine
  作者：Bhuttu Khan、Ruchir Kant、Dipankar Koley

  DOI：10.1002/adsc.201600177

  日期：2016.7.14

  nickel(II)‐mediated ortho‐iodination of benzamides using molecular iodine has been developed. The process is highly regioselective and furnishes only monoiodinated products. A broad range of arenes and heteroarenes with diverse functional groups provided monoiodinated products in good to excellent yields.

  已经开发出使用分子碘的8-氨基喹啉定向，镍（II）介导的苯甲酰胺邻位碘化方法。该方法是高度区域选择性的，并且仅提供单碘化产物。具有各种官能团的广泛的芳烃和杂芳烃以良好或优异的产率提供了单碘化产物。
• A novel pyrene-containing fluorescent organogel derived from a quinoline-based fluorescent porbe: synthesis, sensing properties, and its aggregation behavior
  作者：Chang-Bo Huang、Li-Jun Chen、Junhai Huang、Lin Xu

  DOI：10.1039/c4ra02373k

  日期：——

  A new family of pyrene-containing compounds 2–4 derived from aminoquinoline-containing fluorescent probe 1 were successfully synthesized and well characterized. The investigation of the absorption and emission spectra of these compounds revealed that the photophysical properties were significantly affected by the substitution of pyrene. Moreover, these compounds exhibited selective fluorescence behaviour towards Zn2+ in aqueous solution. The gelation properties of these compounds were investigated by the “stable to inversion of a test tube” method. Interestingly, 1,8-bis-substituted compound 4 displayed stable gel-formation properties in acetone, dioxane, tetrahydrofuran, ethyl acetate, chloroform, and dichloromethane. The morphologies of the xerogels were investigated by scanning electron microscopy (SEM) and laser scanning confocal microscopy (LSCM). The concentration- and temperature-dependent emission properties, and concentration- and temperature-variable 1H NMR spectroscopy of compound 4 were investigated, which suggested that both π–π stacking interaction and hydrogen bonding were the driving forces for the process of self-aggregation and the gel formation. In addition, studies on the luminescence properties indicated that 4 had the ability to form a fluorescent organogel with interesting fluorescence behaviour. More importantly, it was found that compound 4 could form a stimuli-responsive gel that had a sensitive gel-to-sol transition response to heating or adding Zn2+.

  从含氨基喹啉的荧光探针1成功合成并表征了一类新的含芘化合物2-4。对这些化合物的吸收和发射光谱的研究表明，光物理性质显著受到芘取代的影响。此外，这些化合物在水溶液中对Zn2+展示了选择性的荧光行为。通过“测试管稳定反转”方法研究了这些化合物的凝胶化性质。有趣的是，1,8-双取代化合物4在丙酮、二氧六环、四氢呋喃、乙酸乙酯、氯仿和二氯甲烷中表现出稳定的凝胶形成性质。通过扫描电子显微镜（SEM）和激光扫描共聚焦显微镜（LSCM）研究了凝胶的形态。研究了化合物4的浓度依赖性和温度依赖性的发射性质，以及浓度和温度可变的1H NMR光谱，结果表明π–π堆积相互作用和氢键是自聚集和凝胶形成过程的驱动力。此外，对发光性质的研究表明，4具有形成具有有趣荧光行为的荧光有机凝胶的能力。更重要的是，发现化合物4能够形成刺激响应性凝胶，对加热或添加Zn2+具有敏感的凝胶-溶胶转变响应。