9-(isothiocyanatomethyl)anthracene | 17660-78-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9-(isothiocyanatomethyl)anthracene
• 英文别名: 9-isothiocyanomethylanthracene；9-Isothiocyanatomethylanthracen；9-(Isothiocyanatomethyl)anthracene
• CAS: 17660-78-5
• 化学式: C₁₆H₁₁NS
• 分子量: 249.336
• InChiKey: KDLHYVXUOQVGGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  44.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9-(isothiocyanatomethyl)anthracene 在 氨 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以29%的产率得到1-(anthracen-9-ylmethyl)thiourea
  参考文献：
  名称：

  Anthracene-Fe3+ ensemble based turn-on fluorescent probes for selective detection of fluoride

  摘要：

  Two new and simple chemosensors, 1-(anthracen-9-ylmethyl)urea (3a) and 1-(anthracen-9-ylmethyl)thiourea (3b) bearing anthracene moiety, were synthesized from anthracen-9-ylmethanamine. Their UV-Vis absorption, fluorescence emission and potential application for the detection of ions were investigated. Of note is that their fluorescence emission excited with 370 nm could be quenched upon addition of Fe3+, whereby the highly selective recognition for Fe3+ was noticed. Furthermore, ensembles based on 3a-Fe3+ and 3b-Fe3+ complexes having the specific binding affinity for F- show rapid and selective detection of F- over other anions with a fluorescence turn-on mode. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2015.06.025
• 作为产物：
  描述：

  2-(蒽-9-基甲基)异吲哚-1,3-二酮 在 sodium hydroxide 、 一水合肼 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 2.0h， 生成 9-(isothiocyanatomethyl)anthracene
  参考文献：
  名称：

  Design and synthesis of preorganized tripodal fluororeceptors based on hydrogen bonding of thiourea groups for optical phosphate ion sensing

  摘要：

  预期存在前组织效应，设计并合成了三脚架型阴离子主体分子。研究表明，两种新型硫脲衍生物，其六取代苯环作为前组织间隔基，能有效识别四面体磷酸二氢根离子。具有吡啶并环部分与硫脲结合位点相邻的三脚架型氟光受体1在加入客体阴离子后，在乙腈中表现出长波长发射。另一方面，通过亚甲基单元与蒽基团相连的三脚架型硫脲受体2在加入阴离子后荧光强度降低。在这两种情况下，发射强度的变化程度依次为H2PO4^- > CH3COO^- > Cl^- ≫ ClO4^-，这与仅有一个结合位点的参考化合物明显不同。这些三脚架型氟光受体的结合常数（Ka）也证实了在该均相溶液系统中对磷酸二氢根离子相对于更基础的醋酸根离子的选择性。利用前组织效应的氟光受体特征显示出有望开发具有特定阴离子选择性的化学离子传感器。

  DOI：

  10.1039/b105913k

文献信息

• Fluorescent Anion Sensor Derived from Cholic Acid: The Use of Flexible Side Chain
  作者：Lei Fang、Wing-Hong Chan、Yong-Bing He、Daniel W. J. Kwong、Albert W. M. Lee

  DOI：10.1021/jo050913h

  日期：2005.9.1

  The fluorescent photoinduced electron transfer (PET) chemosensors 1−3 were synthesized from cholic acid. 1 and 2 containing amidothiourea groups as anion receptive sites demonstrated much higher affinity toward anions than 3 containing traditional thiourea H-bond donating group. Comparative studies on their binding affinity toward carboxylates, dihydrogen phosphate, and halides revealed that the amidothiourea

  荧光光诱导电子转移（PET）化学传感器1 - 3从胆酸合成。含有酰胺基硫脲基团作为阴离子接受位点的1和2与具有传统硫脲基氢键捐赠基团的3相比，对阴离子具有更高的亲和力。对它们与羧酸根，磷酸二氢根和卤化物的结合亲和力的比较研究表明，C17侧链上的酰胺基硫脲部分可与C7和C12上的氢键供体基团协同作用，以结合球形卤素阴离子。观察到通过配位溴离子出乎意料的特定荧光增强1。
• Design, synthesis and photophysical studies of simple fluorescent anion PET sensors using charge neutral thiourea receptors
  作者：Thorfinnur Gunnlaugsson、Anthony P. Davis、Gillian M. Hussey、Juliann Tierney、Mark Glynn

  DOI：10.1039/b404706k

  日期：——

  of the thiourea receptor moiety, altering the sensitivity of the anion recognition. For, the anion selectivity and the degree of the fluorescence quenching were in the order of F(-) > AcO(-) > H(2)PO(4)(-), with Cl(-) or Br(-) not being detected.

  描述了四个用于阴离子的荧光光致电子转移（PET）化学传感器1-4的合成。这些都是基于简单的设计，采用电荷中性的脂族或芳族硫脲阴离子受体通过亚甲基间隔基连接到蒽荧光团上。在这里，阴离子的识别是通过硫脲质子和阴离子之间的1：1氢键发生的，这通过观察DMSO-d（6）中的（1）H NMR的变化得到了证实，其中两个硫脲质子在添加时被移向了低场。阴离子。1-3是为检测阴离子（例如氟离子，乙酸根或磷酸根）而设计的，而4个是为识别N保护的氨基酸而设计的。所有传感器均表现出“理想”行为，其中只有荧光发射在阴离子识别后被淬灭，由于增强了从受体到荧光团激发态的电子转移猝灭效率。通过简单地改变硫脲取代基的性质，可以调节或调节硫脲受体部分的酸度，从而改变阴离子识别的敏感性。因此，阴离子的选择性和荧光猝灭的程度依次为F（-）> AcO（-）> H（2）PO（4）（-），而Cl（-）或Br（-）不被检测到。
• A cholic acid-based fluorescent chemosenor for the detection of ATP
  作者：Hao Wang、Wing-Hong Chan

  DOI：10.1039/b715086e

  日期：——

  A novel ditopic cholic acid-based fluorescent chemosensor for ATP, 1a, was designed and synthesized. Its interactions with phosphates, AMP, ADP, ATP, CTP, GTP, and TTP have been investigated. When ATP was added to a 1 : 1 aqueous CH3CN solution of the sensor at pH 7.4, a significant decrease in fluorescence of 1a was observed, whereas other guest molecules showed a much smaller effect. The complex between 1a and ATP was confirmed through combined UV, 1H, 13C and 31P NMR spectroscopic methods. The uniqueness of the new sensor is that it binds with ATP 33–124 times more selectively than other nucleotides, as evidenced from the respective binding constants. 1a is a highly sensitive sensing probe; as little as 30 nM ATP can cause 15% fluorescence quenching of the sensor.

  我们设计并合成了一种基于二位胆酸的新型 ATP 荧光化学传感器 1a。研究了它与磷酸、AMP、ADP、ATP、CTP、GTP 和 TTP 的相互作用。当在 pH 值为 7.4 的传感器的 1 : 1 CH3CN 水溶液中加入 ATP 时，观察到 1a 的荧光明显减弱，而其他客体分子的影响要小得多。通过紫外、1H、13C 和 31P NMR 光谱组合方法证实了 1a 与 ATP 之间的复合物。这种新型传感器的独特之处在于，它与 ATP 的结合选择性是其他核苷酸的 33-124 倍，这一点可以从各自的结合常数中得到证明。1a 是一种高灵敏度的传感探针；只要 30 nM 的 ATP 就能引起传感器 15% 的荧光淬灭。
• Novel Potent Antagonists of Transient Receptor Potential Channel, Vanilloid Subfamily Member 1:  Structure−Activity Relationship of 1,3-Diarylalkyl Thioureas Possessing New Vanilloid Equivalents
  作者：Young-Ger Suh、Yong-Sil Lee、Kyung-Hoon Min、Ok-Hui Park、Jin-Kwan Kim、Ho-Sun Seung、Seung-Yong Seo、Bo-Young Lee、Yeon-Hee Nam、Kwang-Ok Lee、Hee-Doo Kim、Hyeung-Geun Park、Jeewoo Lee、Uhtaek Oh、Ju-Ok Lim、Sang-Uk Kang、Min-Jung Kil、Jae-yeon Koo、Song Seok Shin、Yung-Hyup Joo、Jin Kwan Kim、Yeon-Su Jeong、Sun-Young Kim、Young-Ho Park

  DOI：10.1021/jm0502790

  日期：2005.9.1

  Recently, 1,3-diarylalkyl thioureas have merged as one of the promising nonvanilloid TRPV1 antagonists possessing excellent therapeutic potential in pain regulation. In this paper, the full structure-activity relationship for TRPV1 antagonism of a novel series of 1,3-diarylalky thioureas is reported. Exploration of the structure- activity relationship, by systemically modulating three essential pharmacophoric regions, led to six examples of 1,3-dibenzyl thioureas, which exhibit Ca2+ uptake inhibition in rat DRG neuron with IC50 between 10 and 100 nM.
• Cholic-Acid-Based Fluorescent Sensor for Dicarboxylates and Acidic Amino Acids in Aqueous Solutions
  作者：Shun-Ying Liu、Lei Fang、Yong-Bing He、Wing-Hong Chan、Kai-Tai Yeung、Yuen-Kit Cheng、Rong-Hua Yang

  DOI：10.1021/ol052341t

  日期：2005.12.1

  The binding affinities of a cholic-acid-based fluorescent neutral receptor toward dicarboxylate anions and amino acids have been investigated in a CH3OH/H2O system (1:1, 0.01 M HEPES buffer, pH = 7.4) by fluorescence titration experiments. The synthetic host bearing four convergent functionalities strongly binds glutamate via multiple hydrogen bonds with a binding constant of (5.57 +/- 0.88) x 10(6).