2-cyclopentylidene-2-sulfanylacetic acid

• 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: 2-cyclopentylidene-2-sulfanylacetic acid
• 英文别名: 2-cyclopentilyden-2-sulfanylacetic acid；2-cyclopentyliden-2-sulfanylacetic acid；H2cpa
• 化学式: C₇H₁₀O₂S
• 分子量: 158.221
• InChiKey: QCNCEIJWVLBRRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  38.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-cyclopentylidene-2-sulfanylacetic acid 在 KOH 、 NaOH 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 生成 (triphenylphosphane)2(2-cyclopentylidene-2-mercaptoacetato)Au2
  参考文献：
  名称：

  2-环戊基-2-硫烷基乙酸和相关配合物的双核金（I）-银（I）衍生物：合成、晶体结构、性质和抗肿瘤活性

  摘要：

  双核配合物 [AgAu(PPh3)2cpa]（H2cpa = 2-环戊基-2-硫烷基乙酸）是通过用 Ag(PPh3)NO3 处理前体 [Au(PPh3)(Hcpa)] 制备的。通过光谱方法（IR；1H、13C、31P NMR）和质谱法对该配合物进行了表征，并通过单晶 X 射线衍射研究解析了其结构。进行了发光和理论研究，并在体外研究了对 HeLa-229、A2780 和 A2780cis 细胞系的抗肿瘤活性。相关的金(I)-金(I)、[(AuPPh3)2cpa]和银(I)-银(I)、[(AgPPh3)2cpa]化合物也在固态和溶液中制备和研究.

  DOI：

  10.1002/ejic.201000959
• 作为产物：
  描述：

  罗丹宁 、 环戊酮 在 盐酸 作用下， 以 水 为溶剂， 生成 2-cyclopentylidene-2-sulfanylacetic acid
  参考文献：
  名称：

  2-环戊基-2-硫烷基乙酸和相关配合物的双核金（I）-银（I）衍生物：合成、晶体结构、性质和抗肿瘤活性

  摘要：

  双核配合物 [AgAu(PPh3)2cpa]（H2cpa = 2-环戊基-2-硫烷基乙酸）是通过用 Ag(PPh3)NO3 处理前体 [Au(PPh3)(Hcpa)] 制备的。通过光谱方法（IR；1H、13C、31P NMR）和质谱法对该配合物进行了表征，并通过单晶 X 射线衍射研究解析了其结构。进行了发光和理论研究，并在体外研究了对 HeLa-229、A2780 和 A2780cis 细胞系的抗肿瘤活性。相关的金(I)-金(I)、[(AuPPh3)2cpa]和银(I)-银(I)、[(AgPPh3)2cpa]化合物也在固态和溶液中制备和研究.

  DOI：

  10.1002/ejic.201000959

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 and antimicrobial activities of silver(<scp>i</scp>) sulfanylcarboxylates. Structural isomers with identically or unequally coordinated Ag centers in an Ag₄S₄ring
  作者：Elena Barreiro、José S. Casas、María D. Couce、Agustín Sánchez、Rafael Seoane、José Sordo、José M. Varela、Ezequiel M. Vázquez-López

  DOI：10.1039/b702936e

  日期：——

  We have investigated the reactions of silver nitrate and 3-(aryl)-2-sulfanylpropenoic acids [H(2)xspa, x: p = 3-phenyl-, f = 3-(2-furyl)-, t = 3-(2-thienyl)-, py = 3-(2-pyridyl)-] and 2-cyclopentylidene-2-sulfanylacetic acid (H(2)L) in 1 : 1 and 2 : 1 molar ratios. The 1 : 1 molar ratio gave compounds of type [Ag(HL)]; reaction of these compounds with diisopropylamine and NaOH gave [HQ][Ag(L)] (HQ

  我们已经研究了硝酸银与3-（芳基）-2-硫烷基丙二酸[H（2）xspa，x：p = 3-苯基-，f = 3-（2-呋喃基）-，t = 3- （2-噻吩基）-，py ＝ 3-（2-吡啶基）-]和2-环戊叉基-2-磺基乙酸（H（2）L）的摩尔比为1：1和2：1。摩尔比为1：1，得到[Ag（HL）]类型的化合物；这些化合物与二异丙胺和NaOH的反应分别得到[HQ] [Ag（L）]（HQ =二异丙基铵）和Na [Ag（L）] x H（2）O。这些化合物，以及以1：2摩尔比获得的[Ag（2）（L）]类型的化合物，均已通过IR和NMR（（1）H和（13）C）光谱进行了分离和表征。在某些情况下，还可以使用（109）Ag NMR光谱和ESI-MS光谱。[HQ] [Ag（pspa）]（11）的晶体结构，其中检测到结构异构体的存在，和[HQ] [Ag（cpa）]（15）是通过X射线衍射法测定的。测试了复合物对
• 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.
• Synthesis, characterization and antibacterial activity of some new triphenyltin(IV) sulfanylcarboxylates: Crystal structure of [(SnPh3)2(p-mpspa)], [(SnPh3)2(cpa)] and [(SnPh3)2(tspa)(DMSO)]
  作者：Pedro Álvarez-Boo、José S. Casas、María D. Couce、Rosa Farto、Vanesa Fernández-Moreira、Eduardo Freijanes、José Sordo、Ezequiel Vázquez-López

  DOI：10.1016/j.jorganchem.2005.09.012

  日期：2006.1

  Five new triphenyltin(IV) sulfanylcarboxylates of the general formula [(SnPh3)(2)L] (L = pspa, tspa, fspa, p-mpspa or cpa, where p = 3-(2-phenyl)-, t = 3-(2-thienyl)-, f = 3-(2-furyl)-, p-mp = 3-(4-methoxyphenyl)-, spa = 2-sulfanylpropenoato and cpa = 2-cyclopentilyden-2-sulfanylacetate) have been synthesized by reacting triphenyltin(IV) hydroxide with the corresponding acid in ethanol/acetone. The complexes have been characterized by elemental analysis and mass spectrometry and by vibrational and NMR (H-1, C-13, Sn-119) spectroscopies. In the case of [(SnPh3)(2)(p-mpspa)] and [(SnPh3)(2)(cpa)], X-ray structural studies showed that in both compounds each Sri atom is coordinated to three phenyl C atoms and to one S or O atom of the bridge ligand L. All five complexes are active against strains of Staphylococcus aureus, but are inactive against Escherichia coli and Pseudomonas aeruginosa. From a solution of [(SnPh3)(2)(tspa)] in DMSO-d(6) the new complex [(SnPh3)(2)(tspa)(DMSO)] was isolated. The single-crystal X-ray diffractometric study of this complex is also reported, showing that both Sn atoms are bridged by the tspa ligand, whereas the molecule of DMSO is coordinated to one of the tin atoms via the oxygen atom. (c) 2005 Elsevier B.V. All rights reserved.