β-Keto-thiobuttersaeure-S-isopropylester | 15780-62-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: β-Keto-thiobuttersaeure-S-isopropylester
• 英文别名: Acetoacetic acid, 1-thio-, S-isopropyl ester；S-propan-2-yl 3-oxobutanethioate
• CAS: 15780-62-8
• 化学式: C₇H₁₂O₂S
• 分子量: 160.237
• InChiKey: VNWWAALNZPUNNP-UHFFFAOYSA-N

物化性质

• 沸点：
  219.5±23.0 °C(Predicted)
• 密度：
  1.049±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  59.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  β-Keto-thiobuttersaeure-S-isopropylester 在 盐酸 、 硫化氢 作用下， 以 乙腈 为溶剂， 生成 3-Thioxo-thiol-buttersaeure-isopropylester
  参考文献：
  名称：

  Studies on enethiols—III

  摘要：

  DOI：

  10.1016/s0040-4020(01)96327-6
• 作为产物：
  描述：

  2,2,6-三甲基-4H-1,3-二英-4-酮 、 异丙硫醇 以 甲苯 为溶剂， 生成 β-Keto-thiobuttersaeure-S-isopropylester
  参考文献：
  名称：

  Structure–activity relationships of 1,4-dihydropyridines that act as enhancers of the vanilloid receptor 1 (TRPV1)

  摘要：

  Vanilloid agonists such as capsaicin activate ion flux through the TRPV1 channel, a heat- and ligand-gated cation channel that transduces painful chemical or thermal stimuli applied to peripheral nerve endings in skin or deep tissues. We have probed the SAR of a variety of 1,4-dihydropyridine (DHP) derivatives as novel 'enhancers' of TRPV1 activity by examining changes in capsaicin-induced elevations in Ca-45(2+)-uptake in either cells ectopically expressing TRPV1 or in cultured dorsal root ganglion (DRG) neurons. The enhancers increased the maximal capsaicin effect on Ca-45(2+)-uptake by typically 2- to 3-fold without producing an action when used alone. The DHP enhancers contained 6-aryl substitution and small alkyl groups at the 1 and 4 positions, and a 3-phenylalkylthioester was tolerated. Levels of free intracellular Ca2+, as measured by calcium imaging, were also increased in DRG neurons when exposed to the combination of capsaicin and the most efficacious enhancer 23 compared to capsaicin alone. Thus, DHPs can modulate TRPV1 channels in a positive fashion. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2008.08.048

文献信息

• Studies of Acetothiolacetate
  作者：Shinichi Motoki、Tadao Sato

  DOI：10.1246/bcsj.42.1322

  日期：1969.5

  acetothiolacetate (I) in the presence of triethylamine. The ester I underwent a thermal condensation to give dehydroacetic acid (III), with the liberation of mercaptan, merely upon heating, and the reaction was effectively promoted in the presence of triethylamine. The ester I reacted with alkyl halide and acyl halide in dioxane to give α-alkyl and α-acylacetothiolacetate (II) respectively. Ethyl acetothiolacetate

  在三乙胺的存在下，乙烯酮二聚体与硫醇反应得到乙酰硫代乙酸酯(I)。酯Ⅰ经过热缩合得到脱氢乙酸（Ⅲ），仅在加热时释放出硫醇，并且在三乙胺的存在下有效地促进了反应。酯 I 与卤代烷和酰卤在二恶烷中反应，分别得到 α-烷基和 α-酰基乙酰硫代乙酸酯 (II)。乙酰硫代乙酸乙酯、α-甲基-乙酰硫代乙酸乙酯和α-乙酰基乙酰硫代乙酸乙酯与氧化汞在低温下反应分别生成二乙酰丙酮(VI)、甲乙酮和脱氢乙酸(III)。
• Determination of tautomeric phenotypes of β-thioxo esters and characterization of the tautomeric enethiolic constituents by means of13C NMR spectroscopy
  作者：F. Duus、P. E. Hansen

  DOI：10.1002/mrc.1270220105

  日期：1984.1

  AbstractThe 13C NMR spectra of 28 enethiolizable β‐thioxo esters and 6 enethiolizable β‐thioxo thioloesters have been recorded in order to establish the tautomeric phenotypes of these compounds. All compounds investigated are essentially enethiolic. The carbonyl‐conjugated (Z)‐enethiol form is the exclusive or predominant tautomer of open‐chain β‐thioxo esters and thioloesters, thioacylmalonates and medium‐sized 2‐alkoxycarbonylcycloalkanethiones. The carbonyl‐conjugated (E)‐enethiol form is identifiable for open‐chain α‐unsubstituted β‐thioxo esters and thioloesters, and abundant for open‐chain α‐substituted β‐thioxo esters. Non‐conjugated enethiol forms [i.e. (Z)‐ and (E)‐isomeric β,γ‐unsaturated β‐mercapto esters] are abundant tautomeric constituents of ω‐substituted and higher 2‐alkoxycarbonylcycloalkanethiones. The chemical shifts of the carbon atoms directly involved in the tautomeric change have been rationalized in terms of substituent screening contributions. Deuterium isotope effects on the central carbon atoms of selected deuterio‐enethiolic compounds have been measured in order to depict the ester group rotamerism in CO‐conjugated (Z)‐enethiols. The abundance of the CO‐conjugated (E)‐enethiols, as well as the preferred population of the non‐conjugated (Z)‐enethiol form relative to the non‐conjugated (E)‐enethiol form, is rationalized in terms of the occurrence of a no‐bond interaction between the lone‐pair electrons of the enethiolic sulphur atom and the ‘chelating’ methylene hydrogen atoms of cis‐alkyl groups.
• 3,4-Dihydropyrimidin-2(1<i>H</i>)-ones as Antagonists of the Human A_2B Adenosine Receptor: Optimization, Structure–Activity Relationship Studies, and Enantiospecific Recognition
  作者：María Majellaro、Willem Jespers、Abel Crespo、María J. Núñez、Silvia Novio、Jhonny Azuaje、Rubén Prieto-Díaz、Claudia Gioé、Belma Alispahic、José Brea、María I. Loza、Manuel Freire-Garabal、Carlota Garcia-Santiago、Carlos Rodríguez-García、Xerardo García-Mera、Olga Caamaño、Christian Fernandez-Masaguer、Javier F. Sardina、Angela Stefanachi、Abdelaziz El Maatougui、Ana Mallo-Abreu、Johan Åqvist、Hugo Gutiérrez-de-Terán、Eddy Sotelo

  DOI：10.1021/acs.jmedchem.0c01431

  日期：2021.1.14
• HASEGAWA, TADASHI;SHIMIZU, TOSHIO;IWASAKI, KAZUHIKO;OGUCHI, SHOSHICHI, BULL. CHEM. SOC. JAP., 1983, 56, N 6, 1869-1870
  作者：HASEGAWA, TADASHI、SHIMIZU, TOSHIO、IWASAKI, KAZUHIKO、OGUCHI, SHOSHICHI

  DOI：——

  日期：——
• Structure–activity relationships of 1,4-dihydropyridines that act as enhancers of the vanilloid receptor 1 (TRPV1)
  作者：Eun Joo Roh、Jason M. Keller、Zoltan Olah、Michael J. Iadarola、Kenneth A. Jacobson

  DOI：10.1016/j.bmc.2008.08.048

  日期：2008.10

  Vanilloid agonists such as capsaicin activate ion flux through the TRPV1 channel, a heat- and ligand-gated cation channel that transduces painful chemical or thermal stimuli applied to peripheral nerve endings in skin or deep tissues. We have probed the SAR of a variety of 1,4-dihydropyridine (DHP) derivatives as novel 'enhancers' of TRPV1 activity by examining changes in capsaicin-induced elevations in Ca-45(2+)-uptake in either cells ectopically expressing TRPV1 or in cultured dorsal root ganglion (DRG) neurons. The enhancers increased the maximal capsaicin effect on Ca-45(2+)-uptake by typically 2- to 3-fold without producing an action when used alone. The DHP enhancers contained 6-aryl substitution and small alkyl groups at the 1 and 4 positions, and a 3-phenylalkylthioester was tolerated. Levels of free intracellular Ca2+, as measured by calcium imaging, were also increased in DRG neurons when exposed to the combination of capsaicin and the most efficacious enhancer 23 compared to capsaicin alone. Thus, DHPs can modulate TRPV1 channels in a positive fashion. Published by Elsevier Ltd.