N-(9-anthryl)piperidine | 117920-85-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: N-(9-anthryl)piperidine
• 英文别名: 1-Anthracen-9-ylpiperidine；1-anthracen-9-ylpiperidine
• CAS: 117920-85-1
• 化学式: C₁₉H₁₉N
• 分子量: 261.367
• InChiKey: FSGOLIVSVKSCJZ-UHFFFAOYSA-N

物化性质

• 沸点：
  455.1±14.0 °C(Predicted)
• 密度：
  1.136±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  哌啶 、 蒽酮 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 40.0h， 以88%的产率得到N-(9-anthryl)piperidine
  参考文献：
  名称：

  Rapid intermolecular electron transfer specific to the Zwitterionic form of N-(9-(10-hydroxyanthryl))piperidine (HAP)

  摘要：

  The acid-catalyzed condensation of anthrone with excess piperidine affords both N-anthrylpiperidine (80-85%) and HAP (5-10%). The H-1 and C-13 NMR spectra of N-(9-anthryl)piperidine are unexceptional and consistent with the structure assignment. However, the NMR spectra of HAP in DMSO-d6 reveal, except for impurities, only resonances for the aliphatic protons or carbons. Treatment of the DMSO-d6 solution with either strong acid or base results in appearance of the expected aromatic protons or carbons, with integrations and/or chemical shifts as expected for the predicted ionic forms of HAP produced under these conditions. We have interpreted the unusual NMR behavior of HAP in DMSO-d6 in terms of intermolecular electron transfer with an impurity of the corresponding O-centered radical, observable by ESR. Of the four ionization states available to 10-N-piperidinylanthranol, only the zwitterionic form exhibits electron transfer that is rapid and reversible. The results of NMR studies on the N-methylated derivative of HAP are consistent with this interpretation.

  DOI：

  10.1021/ja00005a009

文献信息

• Modified (NHC)Pd(allyl)Cl (NHC = <i>N</i>-Heterocyclic Carbene) Complexes for Room-Temperature Suzuki−Miyaura and Buchwald−Hartwig Reactions
  作者：Nicolas Marion、Oscar Navarro、Jianguo Mei、Edwin D. Stevens、Natalie M. Scott、Steven P. Nolan

  DOI：10.1021/ja057704z

  日期：2006.3.1

  activation step. This translates into higher catalytic activity in the Suzuki-Miyaura and Buchwald-Hartwig reactions, allowing for the coupling of unactivated aryl chlorides at room temperature in minutes. In the Suzuki-Miyaura reaction, aryl triflates, bromides, and chlorides react with boronic acids using very low catalyst loading. In the N-aryl amination reaction, a wide range of substrates has been

  一系列 (NHC)Pd(R-烯丙基)Cl 配合物 [NHC: IPr = N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene, SIPr = N,N'-bis(2,6 -二异丙基苯基)-4,5-二氢咪唑-2-亚基；R = H, Me, gem-Me2, Ph] 已被合成并充分表征。与 (NHC)Pd(烯丙基)Cl 相比，烯丙基支架末端位置的取代有利于更容易的活化步骤。这在 Suzuki-Miyaura 和 Buchwald-Hartwig 反应中转化为更高的催化活性，允许在室温下在几分钟内偶联未活化的芳基氯化物。在 Suzuki-Miyaura 反应中，芳基三氟甲磺酸酯、溴化物和氯化物使用非常低的催化剂负载量与硼酸反应。在N-芳基胺化反应中，广泛的底物得到了有效偶联；伯-, 仲-, 烷基-, 或芳基胺与未活化、中性和活化的芳基氯化物和溴化物以
• The effect of regioisomerism on the solid-state fluorescence of bis(piperidyl)anthracenes: structurally simple but bright AIE luminogens
  作者：Shunsuke Sasaki、Kazunobu Igawa、Gen-ichi Konishi

  DOI：10.1039/c5tc00946d

  日期：——

  A series of regioisomers of piperidylanthracenes (PA) and bis(piperidyl)anthracenes (BPA) were synthesized and their photophysical properties examined in solution, suspension, and the solid state. Aggregation-induced emission (AIE) was observed only for 1,4-BPA and 9,10-BPA, in which two piperidyl groups are substituted at the anthracene moiety in the para-position with respect to each other. Compared

  合成了一系列哌啶基蒽（PA）和双（哌啶基）蒽（BPA）的区域异构体，并在溶液，悬浮液和固体状态下研究了它们的光物理性质。仅对于1，4-BPA和9，10-BPA观察到聚集诱导的发射（AIE），其中两个哌啶基在对位的蒽部分彼此取代。相比以前报道AIE luminogens，这些可以容易地获得对位-取代的BPA S，显示出几个独特的和有益的特征，诸如结构简单，亮固态荧光（Φ FL = 0.49和0.86对1,4-BPA和9,10-BPA），可调的荧光发射和较大的斯托克斯位移。漫反射和荧光寿命测量的结果表明，PA s和BPA s本质上具有有效的非辐射过渡途径，而1,4-BPA和9,10-BPA可以克服该途径。1,4-BPA的X射线晶体学分析表明，不希望有的发色团间的相互作用可以被最小化，而TD-DFT计算表明1,4-BPA的斯托克斯位移增强了 由相邻哌啶基部分之间的严重电子排斥引起，这可能导致缺乏自我吸收。
• Lellmann; Buettner, Chemische Berichte, 1890, vol. 23, p. 1387
  作者：Lellmann、Buettner

  DOI：——

  日期：——
• Barnett; Cook; Matthews, Recueil des Travaux Chimiques des Pays-Bas, 1925, vol. 44, p. 217,219
  作者：Barnett、Cook、Matthews

  DOI：——

  日期：——
• Rapid intermolecular electron transfer specific to the Zwitterionic form of N-(9-(10-hydroxyanthryl))piperidine (HAP)
  作者：Robert W. Sweger、Anthony W. Czarnik

  DOI：10.1021/ja00005a009

  日期：1991.2

  The acid-catalyzed condensation of anthrone with excess piperidine affords both N-anthrylpiperidine (80-85%) and HAP (5-10%). The H-1 and C-13 NMR spectra of N-(9-anthryl)piperidine are unexceptional and consistent with the structure assignment. However, the NMR spectra of HAP in DMSO-d6 reveal, except for impurities, only resonances for the aliphatic protons or carbons. Treatment of the DMSO-d6 solution with either strong acid or base results in appearance of the expected aromatic protons or carbons, with integrations and/or chemical shifts as expected for the predicted ionic forms of HAP produced under these conditions. We have interpreted the unusual NMR behavior of HAP in DMSO-d6 in terms of intermolecular electron transfer with an impurity of the corresponding O-centered radical, observable by ESR. Of the four ionization states available to 10-N-piperidinylanthranol, only the zwitterionic form exhibits electron transfer that is rapid and reversible. The results of NMR studies on the N-methylated derivative of HAP are consistent with this interpretation.