1-pyrenyl isocyanate | 108562-21-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 1-pyrenyl isocyanate
• 英文别名: 1-pyrene isocyanate；Pyrene isocyanate；1-isocyanatopyrene
• CAS: 108562-21-6
• 化学式: C₁₇H₉NO
• 分子量: 243.265
• InChiKey: ORMKUBWIWXXRRL-UHFFFAOYSA-N

物化性质

• 沸点：
  409.9±14.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-pyrenyl isocyanate 在 次氯酸叔丁酯 、 sodium ethanolate 作用下， 以 乙醇 、 乙酸乙酯 、 苯 为溶剂， 反应 3.25h， 生成 4-(1-Pyrenyl)-1,2,4-triazolin-3,5-dion
  参考文献：
  名称：

  Synthetic studies on 4,5-dihydro-3H-1,2,4-triazole-3,5-diones bearing fluorogenic residues at N-4

  摘要：

  已经合成了一些荧光的4,5-二氢-3H-1,2,4-三唑-3,5-二酮。在4-[6-(5-二甲氨基-1-萘磺酰胺)己基]-4,5-二氢-3H-1,2,4-三唑-3,5-二酮4a3的活化萘环上，三唑二酮基团的内外电亲核取代反应导致快速分解。4-芘-1-基-4,5-二氢-3H-1,2,4-三唑-3,5-二酮4d中的三唑二酮基团的二烯亲和性因空间位阻而显著降低。在后者化合物中插入一个三碳间隔单元，生成3-芘-1-基丙基类似物4e，为分析微量1,3-二烯提供了一种有价值的荧光试剂。粉末状锰酸钡被证明是一种优良的固相氧化剂，可以使尿唑转化为1,2,4-三唑-3,5-二酮。

  DOI：

  10.1039/p19960000167
• 作为产物：
  描述：

  1-芘甲酸 在 草酰氯 、 叠氮基三甲基硅烷 作用下， 以 苯 为溶剂， 反应 48.0h， 生成 1-pyrenyl isocyanate
  参考文献：
  名称：

  Synthesis and biological evaluation of 1,7,8,8a-tetrahydro-3H-oxazolo[3,4-a]pyrazin-6(5H)-ones as antitumoral agents

  摘要：

  A series of 1,7,8,8a-tetrahydro-3H-oxazolo[3,4-a]pyrazin-6(5H)-ones has been synthesized by an intramolecular, palladium(II) catalyzed, aminooxygenation of alkenyl ureas, readily available from glycine allylamides as starting materials. Biological tests showed that the obtained compounds are endowed with an interesting antitumoral activity against two human thyroid cancer cell lines, namely FTC-133 and 8305C, by promoting the apoptotic pathway and DNA fragmentation. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.07.019

文献信息

• Urea and thiourea based anion receptors in solution and on polymer supports
  作者：S. Byrne、K. M. Mullen

  DOI：10.1080/10610278.2017.1394462

  日期：2018.3.4

  solvent effects were observed at the solution:surface interface however in general the anion binding properties of the polymer bound urea and thiourea receptors were maintained. The development of a new series of surface bound anion sensors exploiting the urea or thiourea motif capable of binding anions is reported. The use of high resolution magic angle spinning 1H NMR allows the direct comparison of

  摘要在此我们报告开发了一系列新的表面结合阴离子传感器，利用能够通过氢键相互作用结合阴离子的尿素或硫脲基序。使用高分辨率魔角旋转 1H NMR 可以直接比较溶液中这些受体与束缚在聚合物树脂上的受体的阴离子结合特性。在溶液：表面界面观察到一些分子内氢键和溶剂效应，但是通常聚合物结合的尿素和硫脲受体的阴离子结合特性得以保持。据报道，开发了一系列新的表面结合阴离子传感器，利用能够结合阴离子的尿素或硫脲基序。
• Pyrenylmethyldeoxyadenosine: A 3′-Cap for Universal DNA Hybridization Probes
  作者：Michael Printz、Clemens Richert

  DOI：10.1002/chem.200801587

  日期：2009.3.23

  Effect of a PAH on base pairing: A polycyclic aromatic hydrocarbon (PAH) covalently linked to the N6‐position of a dangling deoxyadenosine residue (see scheme) of an oligonucleotide increases target affinity, but decreases base‐pairing selectivity. Melting point increases of up to 28 °C (14 °C per residue) were observed, and 20 out of 24 mismatch‐containing duplexes are stabilized more strongly by

  PAH对碱基配对的影响：与寡核苷酸悬挂的脱氧腺苷残基的N 6位共价连接的多环芳香烃（PAH）（参见方案）可增加靶标亲和力，但会降低碱基配对的选择性。观察到熔点升高到28°C（每个残基14°C），并且与完全匹配的PAH取代基相比，PAH取代基在24个含错配的双链中更稳定了20个。
• A study of allosteric binding behaviour of a 1,3-alternate thiacalix[4]arene-based receptor using fluorescence signal
  作者：Hirotsugu Tomiyasu、Cheng-Cheng Jin、Xin-Long Ni、Xi Zeng、Carl Redshaw、Takehiko Yamato

  DOI：10.1039/c4ob00551a

  日期：——

  The allosteric binding behaviour of a receptor L bearing a 1,3-alternate conformation based thiacalix[4]arene has been evaluated by fluorescence and ¹H NMR titration experiments.

  受体L结合1,3-交替构象基于硫代杯[4]芳烃的变构行为已通过荧光和1H核磁共振滴定实验进行评估。
• Acid/Base- and Anion-Controllable Organogels Formed From a Urea-Based Molecular Switch
  作者：Sheng-Yao Hsueh、Chun-Ting Kuo、Tsan-Wen Lu、Chien-Chen Lai、Yi-Hung Liu、Hsiu-Fu Hsu、Shie-Ming Peng、Chun-hsien Chen、Sheng-Hsien Chiu

  DOI：10.1002/anie.201004090

  日期：2010.11.22

  A switch in time: Gel–sol transitions of a urea‐based [2]rotaxane gelator are controlled by the degree of solvent exposure of the hydrogen‐bond‐donating urea station and the orientation of the hydrogen‐bond‐accepting CO groups of the interlocked ethylene glycol based macrocycle (N blue, O and macrocycle red, phenyl green). Both acid/base and anion‐exchange control can be used to reversibly transition

  时间上的转换：脲基[2]轮烷胶凝剂的凝胶-溶胶转变是由给氢键的尿素站的溶剂暴露程度和接受氢键的CO基团的方向控制的互锁的乙二醇基大环化合物（N蓝色，O和大环红色，苯基绿色）。酸/碱和阴离子交换控制均可用于在溶液状态和凝胶状态之间可逆地将轮烷中的1-戊醇转化。
• Enantioselective Recognition of Amino Alcohols and Amino Acids by Chiral Binol-Based Aldehydes with Conjugated Rings at the Hydrogen Bonding Donor Sites
  作者：Ji-Young Kim、Raju Nandhakumar、Kwan-Mook Kim

  DOI：10.5012/bkcs.2011.32.4.1263

  日期：2011.4.20

  Novel binol-based uryl and guanidinium receptors having higher ring conjugation at the periphery of the hydrogen bonding donor sites have been synthesized and utilized to study the enantioselective recognition of 1,2-aminoalcohols and chirality conversion of natural amino acids via imine bond formation. There is a remarkable decrease in the stereoselectivites as the conjugation increases at the periphery of hydrogen bonding donor sites. The guanidinium-based receptors show more selectivity towards the amino alcohol than that of the uryl based ones due to its charge reinforced hydrogen bonds. The conversion efficiency of L-amino acids to Damino acids by the uryl-based receptors is higher than that of the guanidinium-based ones.

  我们合成了在氢键供体位点外围具有更高环共轭度的新型二醇基脲基和胍基受体，并利用它们研究了 1,2- 氨基丙醇的对映选择性识别和天然氨基酸通过亚胺键形成的手性转换。随着氢键供体位点外围共轭度的增加，立体选择性明显降低。胍基受体对氨基醇的选择性高于脲基受体，这是因为脲基受体的电荷强化了氢键。尿苷受体将 L-氨基酸转化为达米诺酸的效率高于胍基受体。