acryloyl isothiocyanate | 41606-99-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: acryloyl isothiocyanate
• 英文别名: Acryloylisothiocyanat；Acryloyl-isothiocyanat；prop-2-enoyl isothiocyanate
• CAS: 41606-99-9
• 化学式: C₄H₃NOS
• mdl: MFCD00046812
• 分子量: 113.14
• InChiKey: WCEMVDXZPVFHAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  acryloyl isothiocyanate 、 calcium N-methyldithiocarbamate 以 水 、 丙酮 为溶剂， 反应 0.17h， 以72%的产率得到2-thioxo-[1,3]thiazinan-4-one
  参考文献：
  名称：

  Krus, K.; Masias, A.; Beletskaya, I. P., Journal of Organic Chemistry USSR (English Translation), 1988, vol. 24, # 8, p. 1421 - 1425

  摘要：

  DOI：
• 作为产物：
  描述：

  potassium thioacyanate 、 丙烯酰氯 在 poly(ethylene glycol) monomethyl ether (PEG₆-OH) 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以74%的产率得到acryloyl isothiocyanate
  参考文献：
  名称：

  Hg²⁺-Reactive Double Hydrophilic Block Copolymer Assemblies as Novel Multifunctional Fluorescent Probes with Improved Performance

  摘要：

  We report on novel type of responsive double hydrophilic block copolymer (DHBC)-based multifunctional chemosensors to Hg2+ ions, pH, and temperatures and investigate the effects of thermo-induced micellization on the detection sensitivity. Well-defined DHBCs bearing rhodamine B-based Hg2+-reactive moieties (RhBHA) in the thermoresponsive block, poly(ethylene oxide)-b-poly(N-isopropylacrylamide-co-RhBHA) (PEO-b-P(NIPAM-co-RhBHA)), were synthesized via reversible addition-fragmentation chain transfer (RAFT) polymerization. Nonfluorescent RhBHA moieties are subjected to selective ring-opening reaction upon addition of Hg2+ ions or lowering solution pH, producing highly fluorescent acyclic species. Thus. at room temperature PEO-h-P(NIPAM-co-RhBHA) DHBCs can serve as water-soluble multifunctional and efficient fluorescent chemosensors to Hg2+ ions and pH. Upon heating above the lower critical solution temperature (similar to 36 degrees C) of the PNIPAM block, they self-assemble into micelles possessing P(NIPAM-co-RhBHA) cores and well-solvated PEO coronas, which were fully characterized by dynamic and static laser light scattering. It was found that the detection sensitivity to Hg2+ ions and pH could be dramatically improved at elevated temperatures due to fluorescence enhancement of RhBHA residues in the acyclic form, which were embedded within hydrophobic cores of thermo-induced micellar aggregates. This work represents a proof-of-concept example of responsive DHBC-based multifunctional fluorescent chemosensors for the highly efficient detection of Hg2+ ions, pH, and temperatures with tunable detection sensitivity. Compared to reaction-based small molecule Hg2+ probes in previous literature reports, the integration of stimuli-responsive block copolymers with well-developed small molecule-based selective sensing moieties in the current study are expected to exhibit preferred advantages including enhanced detection sensitivity, water dispersibility, biocompatibility, facile incorporation into devices, and the ability of further functionalization for targeted imaging and detection.

  DOI：

  10.1021/la9024102

文献信息

• Responsive nanogel-based dual fluorescent sensors for temperature and Hg2+ ions with enhanced detection sensitivity
  作者：Changhua Li、Shiyong Liu

  DOI：10.1039/c0jm01828g

  日期：——

  We report on the fabrication of thermoresponsive poly(N-isopropylacrylamide) nanogel-based dual fluorescent sensors for temperature and Hg2+ ions, and the effects of thermo-induced nanogel collapse on the detection sensitivity of Hg2+ ions. Near-monodisperse thermoresponsive nanogels were prepared via emulsion polymerization of N-isopropylacrylamide (NIPAM) and a novel 1,8-naphthalimide-based polarity-sensitive and Hg2+-reactive fluorescent monomer (NPTUA, 3). At room temperature, PNIPAM nanogels labeled with a single type of naphthalimide-based dye (NPTUA) can act as ratiometric Hg2+ probes at the nanomolar level. Upon heating above the phase transition temperature, the fluorescence intensity of NPTUA-labeled nanogels in the absence of Hg2+ exhibit ∼3.4-fold increase due to that NPTUA moieties are now located in a more hydrophobic microenvironment. Moreover, it was observed that the detection sensitivity to Hg2+ can be further improved above the nanogel phase transition temperature. At a nanogel concentration of 0.05 g L−1 and in the same Hg2+ concentration range (0–3.0 equiv.), ∼10 fold and ∼57 fold increase in fluorescence emission intensity ratio changes can be achieved at 25 and 40 °C, respectively.

  我们报告了基于热致伸缩性聚（N-异丙基丙烯酰胺）纳米凝胶的温度和 Hg2+ 离子双荧光传感器的制备，以及热致纳米凝胶塌缩对 Hg2+ 离子检测灵敏度的影响。通过乳液聚合 N-isopropylacrylamide (NIPAM) 和一种新型 1,8-naphthalimide 基极性敏感型 Hg2+ 反应荧光单体 (NPTUA, 3) 制备了近单分散热致塌缩纳米凝胶。在室温下，用一种萘二甲酰亚胺染料（NPTUA）标记的 PNIPAM 纳米凝胶可作为纳摩尔级的 Hg2+ 比率探针。当加热到相变温度以上时，在没有 Hg2+ 的情况下，NPTUA 标记的纳米凝胶的荧光强度会增加 3.4 倍，这是因为 NPTUA 分子现在位于更疏水的微环境中。此外，还观察到在纳米凝胶相变温度以上，对 Hg2+ 的检测灵敏度会进一步提高。当纳米凝胶浓度为 0.05 g L-1 时，在相同的 Hg2+ 浓度范围（0-3.0 等当量）内，25 °C 和 40 °C 时的荧光发射强度比变化分别增加了 10 倍和∼57 倍。
• Nanogel-mediated drug delivery system for anticancer agent: pH stimuli responsive poly(ethylene glycol/acrylic acid) nanogel prepared by gamma irradiation
  作者：Nour E.A. Abd El-Sattar、Sanad Elaslam S.A. El-Hddad、Mohamed M. Ghobashy、Ahmed A. Zaher、Khaled El-Adl

  DOI：10.1016/j.bioorg.2022.105972

  日期：2022.10

  dose of 5 kGy. Compound 4 and its nanogel 5 were synthesized and assessed for their anticancer effects against HepG2, A549, MCF-7 and HCT-116 as dual VEGFR-2 and EGFR tyrosine kinases inhibitors. The molecular design was performed to investigate the binding mode of compound 4 with VEGFR-2 and EGFR receptors. Our compound 5 in nanogel showed enhanced anticancer activities against the four tested cancer

  纳米凝胶作为纳米药物载体的流行在于其可调节的物理性质，并且正在开发具有改进性能的药物颗粒包封能力以满足抗癌剂的多种pH敏感性纳米凝胶。监测 pH 值已被确定为治疗过程中的重要诊断要素。由 50:50% 比例的 (PEG/PMAc) 组成的 pH 敏感纳米凝胶已通过 γ-辐照技术在 5 kGy 的辐照剂量下 交联。 化合物4及其纳米凝胶5合成并评估了它们作为双重 VEGFR-2 和 EGFR 酪氨酸激酶抑制剂对 HepG2、A549、MCF-7 和 HCT-116 的抗癌作用。进行分子设计以研究化合物4与VEGFR-2和EGFR受体的结合模式。我们在纳米凝胶中的化合物5对四种测试的癌细胞系显示出增强的抗癌活性，并且对 VEGFR-2 和 EGFR T790M激酶的抑制活性比衍生物4更高。最后，我们的导数4在 silico 中表现良好计算的 ADMET 配置文件。与索拉非尼和厄洛替尼相比，预计在人体中表现出良好的
• Sineokov,A.P.; Sergeeva,M.E., Journal of Organic Chemistry USSR (English Translation), 1967, vol. 3, p. 1427 - 1429
  作者：Sineokov,A.P.、Sergeeva,M.E.

  DOI：——

  日期：——
• Acyl isothiocyanate and polymer thereof
  申请人：DU PONT

  公开号：US02327985A1

  公开（公告）日：1943-08-31
• Modifying polymer flocculants for the removal of inorganic phosphate from water
  作者：Timothy S. Goebel、Kevin J. McInnes、Scott A. Senseman、Robert J. Lascano、Lucas S. Marchand、Todd A. Davis

  DOI：10.1016/j.tetlet.2011.07.130

  日期：2011.10

  Due to strong hydrogen bonding interactions, thiourea has been shown to have a high affinity for anions such as inorganic phosphate. The interaction between phosphate and thiourea has been used to develop technologies that can detect and even remove phosphate from water. This research investigates the use of thiourea derivatized polymer flocculants for the sequestering of inorganic phosphate from water. The study presented herein describes the development of a thiourea based monomer that was used to create a bi-functional polymer that flocculates suspended solid material as well as sorbs phosphate, removing both from water. The new polymer removed more than 60% of the phosphate from a simulated wastewater sample. The addition of a thiourea trapping group to the polymer more than doubled the amount of phosphate removed from solution compared to control polymers. (C) 2011 Elsevier Ltd. All rights reserved.