2-(3-甲苯基)噻唑烷 | 75808-94-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(3-甲苯基)噻唑烷
• 英文名称: 2-m-tolyl-thiazolidine
• 英文别名: 2-(m-Tolyl)thiazolidine；2-(3-methylphenyl)-1,3-thiazolidine
• CAS: 75808-94-5
• 化学式: C₁₀H₁₃NS
• 分子量: 179.286
• InChiKey: XGRWDOHURTVHMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(3-甲苯基)噻唑烷 在 pyridinium chlorochromate 作用下， 以 溶剂黄146 为溶剂， 生成 2-m-Tolyl-thiazolidine 1-oxide; hydrochloride
  参考文献：
  名称：

  Ananthakrishananadar, P.; Prabhakaran, T. R., Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1993, vol. 32, # 10, p. 877 - 880

  摘要：

  DOI：
• 作为产物：
  描述：

  3-甲基苯甲醛 、 巯基乙胺 以40%的产率得到2-(3-甲苯基)噻唑烷
  参考文献：
  名称：

  Robbe; Fernandez; Dubief, European Journal of Medicinal Chemistry, 1982, vol. 17, # 3, p. 235 - 243

  摘要：

  DOI：

文献信息

• Synthesis of 2-phenylthiazolidine derivatives as cardiotonic agents. I. 2-Phenylthiazolidine-3-thiocarboxamides.
  作者：HIROYUKI NATE、YASUO SEKINE、YASUSHI HONMA、HIDEO NAKAI、HIROSHI WADA、MIKIO TAKEDA、HIDEO YABANA、TAKU NAGAO

  DOI：10.1248/cpb.35.1953

  日期：——

  A series of novel 2-phenylthiazolidine-3-thiocarboxamides (II) was synthesized and tested for positive inotropic activity in the isolated guinea pig heart and in anesthetized dogs. Reaction of the benzaldehydes (VI, XI, XIV and XV) with cysteamine followed by treatment with isothiocyanates readily gave II. Structure-activity relationships were investigated by varying the structural parameters. N-Methyl-2 -phenylthiazolidine-3-thiocarboxamides having an ortho substituent such as a Me or OMe group exhibited significant positive inotropic action, which was not blocked by propranolol. Among the various ortho-alkoxyphenyl derivatives synthesized, the 2- (2- (3- (4-phenylpiperazino) propoxy) phenyl) derivative (I67) was found to exhibit more potent and longerlasting activity than amrinone without any significant effect on heart rate or blood pressure

  一系列新型2-苯基噻唑烷-3-硫代氨基甲酸酯（II）被合成并测试了其在离体豚鼠心脏和麻醉犬中的正性肌力活性。苯甲醛（VI、XI、XIV和XV）与半胱胺反应后，再用异硫氰酸酯处理，即可得到II。通过改变结构参数来研究结构-活性关系。具有邻位取代基如Me或OMe的N-甲基-2-苯基噻唑烷-3-硫代氨基甲酸酯表现出显著的正性肌力作用，且该作用不受普萘洛尔阻断。在合成的各种邻位烷氧基苯基衍生物中，2-（2-（3-（4-苯基哌嗪）丙氧基）苯基）衍生物（I67）显示出比氨力农更强大且持久的活性，而对心率或血压无显著影响。
• Structure–reactivity correlations of substituted 2-phenylthiazolidines
  作者：R. Umarani、G. Radhakrishnan

  DOI：10.1139/v92-252

  日期：1992.7.1

  Systematic investigations of the kinetics of the reactions of ethyl bromoacetate (EBA) and of picryl bromide (PB) with 2-phenylthiazolidines (PT) in 100% ethanol were undertaken at 30, 35, 40, and 45 °C. The most incisive information concerning the Hammett equation comes from the extensive studies on the substituted 2-phenylthiazolidines, establishing linear Hammett plots with negative ρ values. The kinetic data, plotted in a Brønsted fashion against pK_a of the corresponding thiazolidinium ions, yield linear relationships. The activation parameters were computed. The linear relationships between ΔH^≠ and ΔS^≠ signify a consistent mechanism throughout the series.

  在100%乙醇中，对乙基溴乙酸酯（EBA）和硝基溴苯（PB）与2-苯基噻唑啉（PT）的反应动力学进行了系统研究，温度分别为30、35、40和45°C。对取代2-苯基噻唑啉的广泛研究提供了关于Hammett方程最具洞察力的信息，建立了具有负ρ值的线性Hammett图。以对应噻唑啉阳离子的pKa为横坐标，以Brønsted方式绘制的动力学数据呈线性关系。计算了活化参数。ΔH≠与ΔS≠之间的线性关系表明整个系列中存在一致的机理。
• Terol; Fernandez; Robbe, European Journal of Medicinal Chemistry, 1978, vol. 13, # 2, p. 149 - 151
  作者：Terol、Fernandez、Robbe、et al.

  DOI：——

  日期：——
• Ananthakrishnanadar; Prabakaran, Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1996, vol. 35, # 5, p. 431 - 433
  作者：Ananthakrishnanadar、Prabakaran

  DOI：——

  日期：——
• ROBBE, Y.;FERNANDEZ, J. -P.;DUBIEF, R.;CHAPAT, J. -P.;SENTENAC-ROUMANOU, +, EUR. J. MED. CHEM.-CHIM. THER., 1982, 17, N 3, 235-243
  作者：ROBBE, Y.、FERNANDEZ, J. -P.、DUBIEF, R.、CHAPAT, J. -P.、SENTENAC-ROUMANOU, +

  DOI：——

  日期：——