4-sulphocinnamic acid | 13586-83-9

• 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: 4-sulphocinnamic acid
• 英文别名: p-sulfocinnamic acid；4-sulfo-cinnamic acid；Zimtsaeure-sulfonsaeure-(4)；4-Sulfo-zimtsaeure；zosteric acid；(E)-3-(4-sulfophenyl)prop-2-enoic acid
• CAS: 13586-83-9
• 化学式: C₉H₈O₅S
• 分子量: 228.226
• InChiKey: BTNQTHYUMJQUJG-ZZXKWVIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  100
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-sulphocinnamic acid 生成 2,3-dibromo-3-(4-sulfo-phenyl)-propionic acid
  参考文献：
  名称：

  van Duin, Recueil des Travaux Chimiques des Pays-Bas, 1922, vol. 41, p. 408

  摘要：

  DOI：
• 作为产物：
  描述：

  肉桂酸 在 硫酸 、 三氧化硫 作用下， 生成 4-sulphocinnamic acid
  参考文献：
  名称：

  Moore, Journal of the American Chemical Society, 1903, vol. 25, p. 627

  摘要：

  DOI：

文献信息

• Synthesis and auxin activity of substituted 5-phenylazo- and 5-styryl-1-naphthaleneacetic acids
  作者：Emrys W. Thomas、Michael M. Casey、Michael A. Venis

  DOI：10.1016/s0031-9422(00)95132-x

  日期：1993.2

  Abstract Two 5-phenylazo- and two 5-styryl- derivatives of the synthetic auxin 1-naphthaleneacetic acid have been synthesized as potential receptor probes. Only the phenylazo compounds showed appreciable auxin activity in standard elongation tests. Molecular modelling suggests that this activity may be related to the ability to adopt a planar conformation.

  摘要 合成了植物生长素 1-萘乙酸的两种 5-苯基偶氮衍生物和两种 5-苯乙烯基衍生物作为潜在的受体探针。在标准伸长率测试中，只有苯基偶氮化合物显示出可观的生长素活性。分子模型表明，这种活动可能与采用平面构象的能力有关。
• Iron(<scp>ii</scp>) coordination pyrazole complexes with aromatic sulfonate ligands: the role of ether
  作者：Varun Kumar、Mohamed El-Massaoudi、Smaail Radi、Kristof Van Hecke、Aurelian Rotaru、Yann Garcia

  DOI：10.1039/d0nj02823a

  日期：——

  mononuclear Fe(II) coordination complexes including 3,5-dimethyl-1-(2′-pyridyl)-pyrazole (DMPP) and aromatic sulfonate ligands were synthesized and characterized using single crystal-XRD, SQUID magnetometry and 57Fe Mössbauer spectroscopy. The crystal structures of the complexes revealed the unusual coordination of sulfonate groups to Fe(II) ions, leading to an Fe–N4O2 coordination environment. This

  合成了四种新颖的单核Fe（II）杂配铁配合物，包括3,5-二甲基-1-（2'-吡啶基）-吡唑（DMPP）和芳族磺酸盐配体，并使用单晶XRD，SQUID磁力分析法和57 FeMössbauer进行了表征光谱学。配合物的晶体结构揭示了磺酸盐基团与Fe（II）离子的不寻常配位，从而形成了Fe–N 4 O 2配位环境。这种特定的分子布局可能是由乙醚引起的，乙醚被蒸汽扩散到络合介质中以获得结晶络合物。除了产生单晶外，乙醚还改变了普通FeN的自组装过程6同源性协调环境。磁化率测量表明，所有络合物在所有温度下均保持顺磁性。除[Fe（DMPP） 2（tos） 2 ]随时间推移而被57 FeMössbauer光谱学建议部分氧化为Fe（ III）以外，其他所有元素均在空气中稳定。
• Process for making arylacrylic acids and their esters
  申请人：GIVAUDAN-ROURE (INTERNATIONAL) S.A.

  公开号：EP0553668A2

  公开（公告）日：1993-08-04

  A "one-pot" process for the palladium catalyzed coupling of a diazonium salt with an olefinic bond, in the aqueous medium in which the diazonium salt is made, by employing a carboxylic acid as a solvent, is described. Arylacrylic acids and their esters, e.g. the cinnamates, can be produced at low catalyst concentration without first isolating the diazonium salt. The process is in particular applied to the synthesis of 2-ethylhexyl p-methoxycinnamate.

  本发明描述了一种钯催化重氮盐与烯烃键偶联的 "一步法 "工艺，在制造重氮盐的水介质中，使用羧酸作为溶剂。芳基丙烯酸及其酯类（如肉桂酸酯）可以在低催化剂浓度下生产，而无需首先分离重氮盐。该工艺尤其适用于合成对甲氧基肉桂酸 2-乙基己酯。
• Moore; Tucker, Journal of the American Chemical Society, 1927, vol. 49, p. 265
  作者：Moore、Tucker

  DOI：——

  日期：——
• 8-(Sulfostyryl)xanthines: water-soluble A2A-selective adenosine receptor antagonists11Preliminary results were presented at the International Symposium “Purines ’96” in Milan, Italy; abstract published in Drug Dev. Res. 1996, 37, 112.
  作者：Christa E. Müller、Jesús Sandoval-Ramı́rez、Ulrike Schobert、Uli Geis、Wolfram Frobenius、Karl-Norbert Klotz

  DOI：10.1016/s0968-0896(98)00025-x

  日期：1998.6

  8-(Sulfostyryl)xanthine derivatives were synthesized as water-soluble A(2A)-selective adenosine receptor (AR) antagonists, meta- and para-sulfostyryl-DMPX (3,7-dimethyl-1-propargylxanthine) derivatives 11a and 11b exhibited high affinity to rat AZA-AR in submicromolar concentrations, and were 20- to 30-fold selective versus rat A(1)-AR. Styryl-DMPX derivatives were inactive at human A(2B)- and A(3)-AR. 1,3-Dipropyl-8-p-sulfostyrylxanthine (13) and its 7-methyl derivative (14) showed similar (13) or higher (14) A(2A) affinity than 11a and 11b but showed no (13) or only a low degree (14) of selectivity versus A(1)-, A(2B)-, and A(3)-AR. The A(2A)-selective sulfostyryl-DMPX derivatives exhibit high water-solubility and may be useful research tools for in vivo studies. (C) 1998 Elsevier Science Ltd. All rights reserved.