2-anthraceneisocyanate | 17017-03-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-anthraceneisocyanate
• 英文别名: 2-isocyanatoanthracene；[2]anthryl isocyanate；[2]Anthrylisocyanat
• CAS: 17017-03-7
• 化学式: C₁₅H₉NO
• 分子量: 219.243
• InChiKey: BAPCPEHKRFAZAL-UHFFFAOYSA-N

物化性质

• 熔点：
  207.5-208 °C
• 沸点：
  386.1±11.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• 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：

  2-anthraceneisocyanate 在 1,4-二氧六环 、 氨 、 水 作用下， 生成 [2]anthryl-urea
  参考文献：
  名称：

  The Conjugation of Amino Acids with Isocyanates of the Anthracene and 1,2-Benzanthracene Series

  摘要：

  DOI：

  10.1021/ja01267a082
• 作为产物：
  描述：

  2-蒽甲酸 在 二苯基膦叠氮化物 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 0.5h， 生成 2-anthraceneisocyanate
  参考文献：
  名称：

  通过稀溶液中尿素基团的氢键控制蒽衍生物的分子间光二聚化†

  摘要：

  蒽衍生物的光二聚反应通过利用分子间氢键进行。能够控制取决于取代的网站上的二聚化反应的蒽衍生物是通过使用两个蒽基部分和一个脲基设计中，被称为Ñ，ñ '-dianthracen- Ñ -ylurea，Ñ DAU（Ñ = 1，2和9）分别对称地被1-氨基，2-氨基和9-氨基取代。我们使用吸收，发射和1研究了这些蒽-脲衍生物的准分子发射和光二聚化反应。1 H NMR光谱以及荧光衰减测量。所有衍生物即使在10 -6 M时也显示出其荧光光谱和多种荧光寿命组分的浓度依赖性。显着地，9DAU导致分子间光二聚化反应。在光反应的这些差异Ñ DAU可以在的分子间关联的蒽环的重叠取决于变化Ñ DAU通过分子间脲部分之间的氢键结合。此外，9DAU的二聚化量子产率通过添加乙酸四丁铵（TBAAc）来还原。因此，我们揭示了取代位点和TBAAc的添加影响了蒽-脲衍生物的二聚反应。

  DOI：

  10.1039/c6pp00125d

文献信息

• Photoactivable fluorophores. 1. Synthesis and photoactivation ofo-nitrobenzyl-quenched fluorescent carbamates.
  作者：Richard T. Cummings、Grant A. Krafft

  DOI：10.1016/0040-4039(88)80017-0

  日期：1988.1

  The synthesis and photoactivation of a new type of fluorescent probe, the photoactivable fluorophore (PAF) are described. The PAFs described in this paper consist of fluorescent aromatic amines coupled to substituted nitrobenzyl quenching chromophores via a carbamate linkage. Photoactivation occurs by an intramolecular photo-redox reaction, converting the o-nitrobenzyl group to a labileo-nitrosobenzaldehyde

  描述了新型荧光探针，可光活化的荧光团（PAF）的合成和光活化。本文中描述的PAF由荧光性芳香胺组成，这些胺通过氨基甲酸酯键与取代的硝基苄基猝灭发色团偶联。通过分子内的光-氧化还原反应发生光活化，将邻硝基苄基转化为不稳定的邻硝基亚硝基苯甲醛半缩醛，该片段断裂并失去CO 2释放出荧光胺。还报道了光活化量子产率。
• Photohealable ion gels based on the reversible dimerisation of anthracene
  作者：Aya Saruwatari、Ryota Tamate、Hisashi Kokubo、Masayoshi Watanabe

  DOI：10.1039/c8cc07775d

  日期：——

  We report a photohealable ion gel based on the photodimerisation of anthracene as a dynamic covalent bond. A tetra-arm poly(ethylene glycol) terminally functionalised with anthracene was synthesised and combined with an ionic liquid to form an ion gel. The photodimerisation reaction was utilised to realise photohealing of the ion gels.

  我们报告了基于蒽的光二聚化作为动态共价键的光疗离子凝胶。合成了用蒽末端官能化的四臂聚乙二醇，并与离子液体混合形成离子凝胶。利用光二聚化反应来实现离子凝胶的光修复。
• Preparation of a High-Strength Hydrogel with Slidable and Tunable Potential Functionalization Sites
  作者：Zhao Li、Zhen Zheng、Shan Su、Lin Yu、Xinling Wang

  DOI：10.1021/acs.macromol.5b02359

  日期：2016.1.12

  A hydrogel with tunable potential functionalization sites has been successfully prepared. As potential functionalization sites, (2-hydroxypropyl)-α-CDs (Hy-α-CDs) were introduced into the network of tetrahedron-like poly(ethylene glycol) (tetra-PEG) gel through supramolecular chemistry. In the stage of complexation, poly-pseudo-rotaxane consisting of tetra-PEG macromonomer and Hy-α-CD formed in pregel

  具有可调节的潜在功能化位点的水凝胶已成功制备。作为潜在的官能化位点，通过超分子化学将（2-羟丙基）-α-CD（Hy-α-CD）引入四面体状聚乙二醇（tetra-PEG）凝胶网络中。在络合阶段，在预凝胶溶液中形成了由四-PEG大分子单体和Hy-α-CD组成的聚拟轮烷。动态络合过程和多假结构-轮烷通过NMR实验研究。在凝胶化阶段，通过点击化学完成了一些交联反应。通过ATR-FTIR，XPS，SEM和压缩试验详细表征了所得水凝胶的结构和力学性能。引入水凝胶的Hy-α-CD的数量与聚拟轮烷的结构密切相关，可以通过调节进料比轻松控制。通过Hy-α-CD将蒽作为功能实例引入到水凝胶中，以初步证明潜在的功能化位点的有效性，并且水凝胶还具有进一步多样化功能化的能力。
• Postpolymerization Modification of Hydroxyl-Functionalized Polymers with Isocyanates
  作者：Frank Biedermann、Eric A. Appel、Jesús del Barrio、Till Gruendling、Christopher Barner-Kowollik、Oren A. Scherman

  DOI：10.1021/ma2008018

  日期：2011.6.28

  The postpolymerization functionalization of hydroxyl-group terminated polymers (M-n in the range of 1000-6000 g mol(-1)) such as poly(ethylene glycol) (PEG), poly(N-isopropylacrylamide) (PNIPAM), poly(N,N-dimethylacrylamide) (PDMAM), and poly(tert-butyl acrylate) (PtBA) with a wide range of functional isocyanate derivatives such as azobenzene, and anthracene has been investigated. It was shown by H-1 and C-13 NMR, GPC, Fourier transform infrared spectroscopy (FTIR), and electrospray ionization mass spectrometry (ESI-MS) that a high degree of end-group conversion, typically >98%, with little or no formation of side products can be achieved at ambient temperature. PNIPAM, PDMAM, PtBA, and PHEAM polymers have been obtained by reversible addition-fragmentation chain transfer (RAFT) radical polymerization from a hydroxyl-group containing chain transfer agent (CTA). The formation of the carbamate has been shown to be compatible with the trithiocarbonate end-group of the RAFT polymers. Additionally, this approach allows for the direct functionalization of RAFT polymers without the need of additional steps such as deprotection or aminolysis of the CTA. This route was subsequently used for the preparation of a variety of side-chain functional polymers from poly(N-hydroxyethyl acrylamide) (PHEAM). Three different high yielding methods have been employed to prepare the isocyanates (R-NCO). Either amino or carboxylic acid precursors have been converted into the desired R NCO or hydroxyl group moieties have been reacted with an excess of 1,6-hexamethylene diisocyanate (HDI) to statistically form the monofunctional product.
• 2-Arylureidobenzoic Acids:  Selective Noncompetitive Antagonists for the Homomeric Kainate Receptor Subtype GluR5
  作者：Jon Valgeirsson、Elsebet Ø. Nielsen、Dan Peters、Thomas Varming、Claus Mathiesen、Anders S. Kristensen、Ulf Madsen

  DOI：10.1021/jm030428j

  日期：2003.12.1

  A series of 2-arylureidobenzoic acids (AUBAs) was prepared by a short and effective synthesis, and the pharmacological activity at glutamate receptors was evaluated in vitro and in vivo. The compounds showed noncompetitive antagonistic activity at the kainate receptor subtype GluR5. The most potent compounds showed more than 50-fold selectivity for GluR5 compared to GluR6 and the AMPA receptor subtypes GluR1-4. The structure-activity relationships for the AUBAs showed distinct structural requirements for the substituents on the two aromatic ring systems. Only para-substituents were tolerated on the benzoic acid moiety (ring A), whereas ring B tolerated a variety of substituents, but with a preference for lipophilic substituents. The most potent compounds had a 4-chloro substituent on ring A and 3-chlorobenzene (6b), 2-naphthalene (8h), or 2-indole (8k) as ring B and had IC50 values of 1.3, 1.2, and 1.2,muM, respectively, in a functional GluR5 assay. Compound 6c (IC50 = 4.8 muM at GluR5) showed activity in the in vivo ATPA rigidity test, indicating that 6c has better pharmacokinetic properties than 8h, which was inactive in this test. The AUBAs are the first example of a series of noncompetitive GluR5-selective antagonists and may prove to be important pharmacological tools and leads in the search for therapeutic glutamatergic agents.