3-(2-羟基苯基)-2-硫烷基丙-2-烯酸 | 5765-84-4

• 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
• 中文名称: 3-(2-羟基苯基)-2-硫烷基丙-2-烯酸
• 英文名称: 3-(2-hydroxyphenyl)-2-sulfanylpropenoic acid
• 英文别名: 3-(2-hydroxyphenyl)sulfanylpropenoic acid；H2(o-hpspa)；H2-o-hpspa；2-Mercapto-3-(o-hydroxyphenyl)-acrylsaeure；2-Hydroxy-α-mercapto-zimtsaeure；3-(2-Hydroxyphenyl)-2-sulfanylprop-2-enoic acid；3-(2-hydroxyphenyl)-2-sulfanylprop-2-enoic acid
• CAS: 5765-84-4
• 化学式: C₉H₈O₃S
• 分子量: 196.227
• InChiKey: RXIBZYLJHRYUMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 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：
  58.5
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  3-(2-羟基苯基)-2-硫烷基丙-2-烯酸 、 三苯基氢氧化锡 以 乙醇 、 丙酮 为溶剂， 以60%的产率得到(3-thio-2H-1-benzopyran-2-one)triphenyltin(IV)
  参考文献：
  名称：

  Formation of 3‐Sulfanylcoumarins by SnPh ₃ OH‐Promoted Cyclization of 3‐Aryl‐2‐Sulfanylpropenoic Acids

  摘要：

  AbstractReaction of SnPh3OH with 3‐(2‐hydroxyphenyl)sulfanylpropenoic acid [H2(o‐hpspa)] yielded [SnPh3(SC)], where SC is deprotonated 3‐sulfanylcoumarin (3‐sulfanyl‐2H‐1‐benzopyran‐2‐one, HSC), by a cyclization process. Similarly, when 3‐(2‐hydroxy‐5‐bromophenyl)‐ and 3‐(2‐hydroxy‐3,5‐dibromophenyl)‐2‐sulfanylpropenoic acids were treated with the same tin hydroxide, the cyclization resulted in [SnPh3(BrSC)] and [SnPh3(Br2SC)], where BrSC and Br2SC are the new ligands formed from the deprotonation of 3‐sulfanyl‐6‐bromocoumarin and 3‐sulfanyl‐6,8‐dibromocoumarin, respectively. The new compounds were characterized by elemental analysis, multinuclear NMR (1H, 13C and 119Sn) and vibrational spectroscopy, and mass spectrometry. Single‐crystal X‐ray structures of these complexes all showed that the tin atom is surrounded by three phenyl C atoms and the S and O atoms of the bidentate ligand in a distorted trigonal‐bipyramidal environment. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

  DOI：

  10.1002/ejic.200500237
• 作为产物：
  描述：

  罗丹宁 、 邻甲基苄醇 以58%的产率得到3-(2-羟基苯基)-2-硫烷基丙-2-烯酸
  参考文献：
  名称：

  Formation of 3‐Sulfanylcoumarins by SnPh ₃ OH‐Promoted Cyclization of 3‐Aryl‐2‐Sulfanylpropenoic Acids

  摘要：

  AbstractReaction of SnPh3OH with 3‐(2‐hydroxyphenyl)sulfanylpropenoic acid [H2(o‐hpspa)] yielded [SnPh3(SC)], where SC is deprotonated 3‐sulfanylcoumarin (3‐sulfanyl‐2H‐1‐benzopyran‐2‐one, HSC), by a cyclization process. Similarly, when 3‐(2‐hydroxy‐5‐bromophenyl)‐ and 3‐(2‐hydroxy‐3,5‐dibromophenyl)‐2‐sulfanylpropenoic acids were treated with the same tin hydroxide, the cyclization resulted in [SnPh3(BrSC)] and [SnPh3(Br2SC)], where BrSC and Br2SC are the new ligands formed from the deprotonation of 3‐sulfanyl‐6‐bromocoumarin and 3‐sulfanyl‐6,8‐dibromocoumarin, respectively. The new compounds were characterized by elemental analysis, multinuclear NMR (1H, 13C and 119Sn) and vibrational spectroscopy, and mass spectrometry. Single‐crystal X‐ray structures of these complexes all showed that the tin atom is surrounded by three phenyl C atoms and the S and O atoms of the bidentate ligand in a distorted trigonal‐bipyramidal environment. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

  DOI：

  10.1002/ejic.200500237

文献信息

• Synthesis and antimicrobial activities of gold(I) sulfanylcarboxylates
  作者：Elena Barreiro、José S. Casas、María D. Couce、Agustín Sánchez、Rafael Seoane、Antonio Perez-Estévez、José Sordo

  DOI：10.1007/s13404-011-0040-7

  日期：2012.3

  Reaction of NaAuCl4·H2O and thiodiglycol (1:3 molar ratio) with 3-(aryl)-2-sulfanylpropenoic acids, H2xspa = [x:p = 3-phenyl-, f = 3-(2-furyl)-, t = 3-(2-thienyl)-, o-py = 3-(2-pyridyl)-, Clp = 3-(2-chlorophenyl)-, -o-mp = 3-(2-methoxyphenyl)-, -p-mp = 3-(4-methoxyphenyl)-, -o-hp = 3-(2-hydroxyphenyl)-, -p-hp = 3-(4-hydroxyphenyl)-, diBr-o-hp = 3-(3,5-dibromo-2-hydroxyphenyl)] and 2-cyclopentylidene-2-sulfanylacetic

  NaAuCl4·H2O 和硫二甘醇（1:3 摩尔比）与 3-(芳基)-2-硫烷基丙烯酸反应，H2xspa = [x:p = 3-苯基-，f = 3-(2-呋喃基)-，t = 3-(2-噻吩基)-, o-py = 3-(2-吡啶基)-, Clp = 3-(2-氯苯基)-, -o-mp = 3-(2-甲氧基苯基)-, -p -mp = 3-(4-甲氧基苯基)-, -o-hp = 3-(2-羟基苯基)-, -p-hp = 3-(4-羟基苯基)-, diBr-o-hp = 3-(3 ,5-二溴-2-羟基苯基)] 和 2-亚环戊基-2-硫烷基乙酸 (H2cpa) 以 1:1 的金属/配体摩尔比得到 [Au(Hxspa)] 或 [Au(Hcpa)] 类型的化合物. 这些化合物与二异丙胺反应得到 [HQ][Au(xspa)] 或 [HQ][Au(cpa)]（HQ = 二异丙基铵），然后与 NaOH 反应得到
• Synthesis, Structural Characterization, and Antiinflammatory Activity of Triethylphosphinegold(I) Sulfanylpropenoates of the Type [(AuPEt₃)₂xspa] [H₂xspa = 3-(Aryl)-2-sulfanylpropenoic acid]: an (H₂O)₆ Cluster in the Lattice of the Complexes [(AuPEt₃)₂xspa]·3H₂O
  作者：Elena Barreiro、José S. Casas、María D. Couce、Ángeles Gato、Agustín Sánchez、José Sordo、José M. Varela、Ezequiel M. Vázquez López

  DOI：10.1021/ic800314p

  日期：2008.7.1

  Gold complexes of the type [(AuPEt3)(2)xspa] were prepared by reacting AuPEt3Cl in basic media with the 3-(aryl)-2-sulfanylpropenoic acids H(2)xspa [x = p, Clp, -o-mp, -p-mp, -o-hp, -p-hp, diBr-o-hp, f, t, -o-py; p = 3-phenyl, Clp = 3-(2-chlorophenyl)-, -o-mp = 3-(2-methoxyphenyl)-, -p-mp = 3-(4-methoxyphenyl)-, -o-hp = 3-(2-hydroxyphenyl)-, -p-hp = 3-(4-hydroxyphenyl)-, -diBr-o-hp = 3-(3,5- dibromo-2-hydroxyphenyl)-, t = 3-(2-furyl)-, t = 3-(2-thienyl)-, -o-py = 3-(2-pyridyl); spa = 2-sulfanylpropenoato], and 2-cyclopentylidene-2-sulfanylacetic acid (H(2)cpa). The complexes were characterized by spectroscopic methods (IR, H-1, C-13 and P-31 NMR) and mass spectrometry, and the complexes [(AuPEt3)(2)pspa]center dot 3H(2)O, [(AuPEt3)(2)-p-hpspa]center dot 3H(2)O, [(AuPEt3)(2)tspa)]center dot 3H(2)O, and [(AuPEt3)(2)-o-hpspa] by X-ray diffractometry. The crystals of the first three complexes contain (H2O)(6) clusters hydrogen bonded to [(AuPEt3)2xspa]2 dimer units, whereas in the -o-hpspa derivative the hydrogen bonds are between the monomer [(AuPEt3)2-o-hpspa] units. The antiinflammatory activity of the complexes against plantar edema induced by carrageenan in rats is generally significant, with the values for the o-hpspa and tspa derivatives being particularly high.
• Mono and dinuclear phosphinegold(I) sulfanylcarboxylates: Influence of nuclearity and substitution of PPh 3 for PEt 3 on cytotoxicity
  作者：Elena Barreiro、José S. Casas、María D. Couce、Agustín Sánchez、Angeles Sánchez-Gonzalez、José Sordo、Ezequiel M. Vázquez-López

  DOI：10.1016/j.jinorgbio.2014.05.010

  日期：2014.9

  Gold complexes of the type [Au(PEt3)(Hxspa)] were prepared by reacting triethylphosphinegold(I) chloride in ethanol/water (8:1) with the 3-(aryl)-2-sulfanylpropenoic acids H(2)xspa [x = p = 3-phenyl-; f = 3-(2-furyl)-; t = 3-(2-thienyl)-; py = 3-(2-pyridyl); Clp = 3-(2-Chlorophenyl)-; -o-mp = 3-(2-methoxyphenyl)-; -p-mp = 3-(4-methoxyphenyl)-; -o-hp = 3-(2-hydroxyphenyl)-; -p-hp = 3-(4-hydroxyphenyl)-; -diBr-o-hp = 3-(3,5-dibromo-2-hidroxyphenyl-); spa = 2-sulfanylpropenoato] or 2-cyclopentylidene-2-sulfanylacetic acid (H(2)cpa) and KOH in a 1:1:1 mole ratio. The compounds were characterized by IR spectroscopy and FAB mass spectrometry and by H-1, C-13 and P-31 NMR spectroscopy. The in vitro antitumor activity of these and of the previously described dinuclear [(AuPEt3)(2)(xspa)] complexes against the HeLa-229, A2780 and A2780cis cell lines was determined and compared with those of the analogous PPh3 complexes. The results show that the substitution of the PPh3 ligand by PEt3 is particularly effective in increasing the cytotoxicity of the dinuclear [(AuPR3)(2)(xspa)] complexes, giving rise to compounds that are significantly more active than cisplatin against the aforementioned cell lines. In addition, and as a preliminary test for nephrotoxicity, the cytotoxicity of the most active compounds against the normal renal LCC-PK1 cell line was evaluated and compared with that of cisplatin. (C) 2014 Elsevier Inc. All rights reserved.
• Intra- and intermolecular hydrogen bonds in [Ag(PPh3)3(HL)] complexes [H2L: H2xspa=3(aryl)-2-sulfanylpropenoic acids; H2cpa=2-cyclopentylidene-2-sulfanylacetic acid]
  作者：Elena Barreiro、José S. Casas、María D. Couce、Agustín Sánchez、José Sordo、José M. Varela、Ezequiel M. Vázquez López

  DOI：10.1016/j.poly.2010.09.027

  日期：2011.1

  Compounds of the type [Ag(PPh3)(3)(HL)] [H(2)xspa=3(aryl)-2-sulfanylpropenoic acids: x = Clp [3-(2-chlorophenyl)-], -o-mp [3-(2-methoxyphenyl)-], -p-mp[3-(4-methoxyphenyl)-], -o-hp [3-(2-hydroxyphenyl)-], -p-hp [3-(4-hydroxyphenyl-); H(2)cpa = 2-cyclopentylidene-2-sulfanylacetic acid] were synthesized and characterised by IR and NMR (H-1 C-13 and P-31) spectroscopy and by FAB mass spectrometry. The crystal structures of [Ag(PPh3)(3)(HClpspa)], [Ag(PPh3)(3)(H-o-mpspa)], [Ag(PPh3)(3)(H-p-mpspa)] and [Ag(PPh3)(3)-(Hcpa)] reveal the presence of discrete molecular units containing an intramolecular O-H center dot center dot center dot S hydrogen bond between the S atom and one of the O atoms of the COOH group. This intramolecular hydrogen bond remains in [Ag(PPh3)(3)(H-o-hpspa)]center dot EtOH and [Ag(PPh3)(3)(H-p-hpspa)] but in both cases polymeric structures are built on the basis of O-H center dot center dot center dot O interactions that involve the -OH substituent of the phenyl group of the sulfanylpropenoate fragment. (C) 2010 Elsevier Ltd. All rights reserved.