sodium 4-chlorocinnamate | 2532-20-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: sodium 4-chlorocinnamate
• 英文别名: sodium 3-(4-chlorophenyl)acrylate；Sodium 3-(4-chlorophenyl)prop-2-enoate；sodium;3-(4-chlorophenyl)prop-2-enoate
• CAS: 2532-20-9
• 化学式: C₉H₆ClO₂*Na
• 分子量: 204.588
• InChiKey: VGGNHJUMMSTSHB-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.89
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  lanthanide(III)chloride heptahydrate 、 sodium 4-chlorocinnamate 以 水 为溶剂， 反应 3.0h， 以81%的产率得到[La(4-Clcinn)₃]·2H₂O
  参考文献：
  名称：

  Dual investigation of lanthanide complexes with cinnamate and phenylacetate ligands: Study of the cytotoxic properties and the catalytic oxidation of styrene

  摘要：

  Eleven lanthanide compounds [Y(cinn)(3)] (1), [La(cinn)(3)] (2), [La(4-OMecinn)(3)]center dot 2H(2)O (3), [La(4-Clcinn)(3)]center dot 2H(2)O (4), [La(4-OMephac)(3)]center dot 4H(2)O (5), [La(4-Clphac)(3)]center dot 3H(2)O (6), [Ce(cinn)(3)] (7), [Nd(cinn)(3)] (8), [Sm(cinn)(3)]center dot H2O (9), [Yb(cinn)(3)] (10) and [Sm(4-OMephac)(3)]center dot H2O (11) containing carboxylato ligands (cinn = cinnamate; 4-OMecinn = 4-methoxicinnamate; Clcinn = 4-chlorocinnamate; 4-OMephac = 4-methoxyphgnylacetate; 4-Clphac = 4-chlorophenylacetate) have been synthesized and characterized by elemental analysis, IR, H-1 and C-13 NMR spectroscopy, thermal analysis and X-ray diffraction powder patterns. In addition, compound 11 was characterized by single crystal X-ray diffraction studies. The cytotoxic activity of these complexes has been tested against three different human tumour cell lines HL60 (human promyelocytic leukemia), K562 (human erythromyeloblastoid leukemia) and MCF7 (breast cancer), observing a very modest cytotoxic activity for all tested compounds. In addition, toxicity tests to macrophages and erythrocytes have also been carried out, observing that none of the compounds is toxic against these immunocompetent cells. Finally, all the synthesized compounds have been tested as catalysts for styrene oxidation observing conversions higher than 50% after 19 h of reaction as well as a relatively high selectivity to two main products benzaldehyde (BzA) and 1-phenylethane-1,2-diol (PhED). Complex 7 presents the higher conversion (99.56%) with a relatively high selectivity towards PhED of 72.07%. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2014.02.040
• 作为产物：
  描述：

  对氯肉桂酸 在 sodium hydroxide 作用下， 以 水 为溶剂， 生成 sodium 4-chlorocinnamate
  参考文献：
  名称：

  新型卟啉-肉桂酸缀合物的合成与表征。

  摘要：

  通过将5-（4-羟基苯基）-10,15,20-三苯基卟啉（1）与不同的取代肉桂酸缩合，合成了一系列新型的卟啉-肉桂酸（卟啉/ CA）共轭物（4a-4c）。由于CAs的生物学活性以及卟啉在癌症的光动力疗法（PDT）中的应用，导致通过烷基连接子（CAs）的转移。还制备了它们的相关锌（II）配合物（5a-5c）。这些新型化合物已通过1H NMR，红外（IR），质谱（Ms）和元素分析得到了充分表征。通过吸收和荧光光谱研究了这些靶分子的光物理性质。在溶液中，还通过紫外-可见光谱研究了pH，酸介质中的离子强度和浓度对4a聚集行为的影响。当pH值在THF水溶液中达到2.0时，变宽的红色Soret带变宽，表明J聚集体的形成。此外，在酸性介质中0.3 M NaCl的较高离子强度导致在THF水溶液中生成J聚集体。Soret带的显着蓝移也表明在THF中以1.1×10-4 M形成4a的H聚集体。

  DOI：

  10.1016/j.saa.2019.117314

文献信息

• Dual investigation of lanthanide complexes with cinnamate and phenylacetate ligands: Study of the cytotoxic properties and the catalytic oxidation of styrene
  作者：Alberto Aragón-Muriel、María Camprubí-Robles、Elena González-Rey、Alfonso Salinas-Castillo、Antonio Rodríguez-Diéguez、Santiago Gómez-Ruiz、Dorian Polo-Cerón

  DOI：10.1016/j.poly.2014.02.040

  日期：2014.9

  Eleven lanthanide compounds [Y(cinn)(3)] (1), [La(cinn)(3)] (2), [La(4-OMecinn)(3)]center dot 2H(2)O (3), [La(4-Clcinn)(3)]center dot 2H(2)O (4), [La(4-OMephac)(3)]center dot 4H(2)O (5), [La(4-Clphac)(3)]center dot 3H(2)O (6), [Ce(cinn)(3)] (7), [Nd(cinn)(3)] (8), [Sm(cinn)(3)]center dot H2O (9), [Yb(cinn)(3)] (10) and [Sm(4-OMephac)(3)]center dot H2O (11) containing carboxylato ligands (cinn = cinnamate; 4-OMecinn = 4-methoxicinnamate; Clcinn = 4-chlorocinnamate; 4-OMephac = 4-methoxyphgnylacetate; 4-Clphac = 4-chlorophenylacetate) have been synthesized and characterized by elemental analysis, IR, H-1 and C-13 NMR spectroscopy, thermal analysis and X-ray diffraction powder patterns. In addition, compound 11 was characterized by single crystal X-ray diffraction studies. The cytotoxic activity of these complexes has been tested against three different human tumour cell lines HL60 (human promyelocytic leukemia), K562 (human erythromyeloblastoid leukemia) and MCF7 (breast cancer), observing a very modest cytotoxic activity for all tested compounds. In addition, toxicity tests to macrophages and erythrocytes have also been carried out, observing that none of the compounds is toxic against these immunocompetent cells. Finally, all the synthesized compounds have been tested as catalysts for styrene oxidation observing conversions higher than 50% after 19 h of reaction as well as a relatively high selectivity to two main products benzaldehyde (BzA) and 1-phenylethane-1,2-diol (PhED). Complex 7 presents the higher conversion (99.56%) with a relatively high selectivity towards PhED of 72.07%. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis and characterization of novel porphyrin-cinnamic acid conjugates
  作者：Baojuan Zhao、Minzhen Wang、Xiang Wang、Pengfei Yu、Na Wang、Fengjuan Li

  DOI：10.1016/j.saa.2019.117314

  日期：2019.12

  A series of novel porphyrin-cinnamic acid (porphyrin/CA) conjugates (4a-4c) have been synthesized by condensation of 5-(4-Hydroxyphenyl)-10,15,20-triphenyl- porphyrin (1) with different substituted cinnamic acids (CAs) through an alkyl linker due to the biological activities of CAs and the application of porphyrins in photodynamic therapy (PDT) of cancer. Their related zinc (II) complexes (5a-5c) were

  通过将5-（4-羟基苯基）-10,15,20-三苯基卟啉（1）与不同的取代肉桂酸缩合，合成了一系列新型的卟啉-肉桂酸（卟啉/ CA）共轭物（4a-4c）。由于CAs的生物学活性以及卟啉在癌症的光动力疗法（PDT）中的应用，导致通过烷基连接子（CAs）的转移。还制备了它们的相关锌（II）配合物（5a-5c）。这些新型化合物已通过1H NMR，红外（IR），质谱（Ms）和元素分析得到了充分表征。通过吸收和荧光光谱研究了这些靶分子的光物理性质。在溶液中，还通过紫外-可见光谱研究了pH，酸介质中的离子强度和浓度对4a聚集行为的影响。当pH值在THF水溶液中达到2.0时，变宽的红色Soret带变宽，表明J聚集体的形成。此外，在酸性介质中0.3 M NaCl的较高离子强度导致在THF水溶液中生成J聚集体。Soret带的显着蓝移也表明在THF中以1.1×10-4 M形成4a的H聚集体。