p-chlorophenylamino-2 dihydro-4,5 thiazole | 56242-68-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: p-chlorophenylamino-2 dihydro-4,5 thiazole
• 英文别名: (4-chloro-phenyl)-(4,5-dihydro-thiazol-2-yl)-amine；(4-Chlor-phenyl)-(4,5-dihydro-thiazol-2-yl)-amin；N-(4-chlorophenyl)-4,5-dihydro-1,3-thiazol-2-amine
• CAS: 56242-68-3
• 化学式: C₉H₉ClN₂S
• mdl: MFCD00174439
• 分子量: 212.703
• InChiKey: DTABQBJFJXOQIQ-UHFFFAOYSA-N

物化性质

• 熔点：
  161 °C
• 沸点：
  330.6±44.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  49.7
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,6-二氯甲基吡啶 、 p-chlorophenylamino-2 dihydro-4,5 thiazole 在 sodium hydride 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 0.5h， 以35%的产率得到N-(4-chlorophenyl)-3-[[6-[[2-(4-chlorophenyl)imino-1,3-thiazolidin-3-yl]methyl]pyridin-2-yl]methyl]-1,3-thiazolidin-2-imine
  参考文献：
  名称：

  Synthesis and Biological Activity of Novel Symmetrical Bis-2-phenyliminothiazolidine Derivatives

  摘要：

  A series of novel symmetrical bis-2-phenyliminothiazolidine derivatives were designed and synthesized. The structures of all the title compounds were characterized by H-1 NMR and, in some cases, by C-13 NMR, IR, and high-resolution mass spectra. Herbicidal activities were examined, and some of these compounds showed selectively herbicidal activity against Triticum aestivum. The type of linker between the two 2-phenyliminothiazolidines was crucial for the biological activities.

  DOI：

  10.1080/10426500600865103
• 作为产物：
  描述：

  p-chlorophenyldithiocarbamic acid triethylamine salt 在 盐酸 、 sodium carbonate 、 三乙胺 作用下， 以 氯仿 、 丙酮 为溶剂， 反应 30.0h， 生成 p-chlorophenylamino-2 dihydro-4,5 thiazole
  参考文献：
  名称：

  Aminothiazines et aminothiazoles analogues ouverts du lévamisole: synthèse et approche du mode d'action nématicide

  摘要：

  DOI：

  10.1016/0223-5234(89)90011-1

文献信息

• Hirashima, Akinori; Tarui, Hiroshi; Eto, Morifusa, Bioscience, Biotechnology and Biochemistry, 1994, vol. 58, # 7, p. 1206 - 1209
  作者：Hirashima, Akinori、Tarui, Hiroshi、Eto, Morifusa

  DOI：——

  日期：——
• Three-dimensional quantitative structure–activity studies of octopaminergic agonists responsible for the inhibition of sex-pheromone production in Hercoverpa armigera
  作者：Akinori Hirashima、Ada Rafaeli、Carina Gileadi、Eiichi Kuwano

  DOI：10.1016/s0968-0896(99)00189-3

  日期：1999.11

  The quantitative structure-activity relationship (QSAR) of octopaminergic agonists responsible for the inhibition of sex-pheromone production in Hercoverpa armigera, was analyzed using physicochemical parameters, molecular shape analysis (MSA), molecular field analysis (MFA), and receptor surface model (RSM), respectively. The dose-response studies were performed in vitro analyzing the effect of these compounds on intracellular cAMP production in the presence of pheromone biosynthesis activating neuropeptide (PBAN) at 1 pmol/intersegment. Six active derivatives were identified in the order of decreasing pheromonostatic activity: 2-(2,6-dimethylanilino)imidazolide (6) > 2-(2-methyl-4-chloroanilino)oxazolidine (1) > clonidine (5) > 2-(2,6-diethylanilino)thiazolidine (8) > 2-(3,5-dichlorobenzylamino)-2-oxazoline (4) > tolazoline (10) which were all active in the nanomolar range in inhibition of cAMP production by 1 pmol PBAN/intersegment. Four other compounds were less active having K-i in the micromolar range. An MSA was tried to obtain QSAR equation that incorporates spatial molecular similarity data of those compounds. MFA on the training set of those compounds evaluated effectively the energy between a probe and a molecular model at a series of points defined by a rectangular or spherical grid. An RSM was generated using some subset of the most active structures. Three-dimensional energetics descriptors were calculated from RSM/ligand interaction and these three-dimensional descriptors were used in QSAR analysis. These results indicate that these derivatives could provide useful information in the characterization and differentiation of octopaminergic receptor types and subtypes. (C) 1999 Elsevier Science Ltd. All rights reserved.
• CAUJOLLE, RAYMOND;AMAROUCH, HAMID;PAYARD, MARC;LOISEAU, PHILIPPE R.;BORIE+, EUR. J. MED. CHEM., 24,(1989) N, C. 287-291
  作者：CAUJOLLE, RAYMOND、AMAROUCH, HAMID、PAYARD, MARC、LOISEAU, PHILIPPE R.、BORIE+

  DOI：——

  日期：——
• Aminothiazines et aminothiazoles analogues ouverts du lévamisole: synthèse et approche du mode d'action nématicide
  作者：Raymond Caujolle、Hamid Amarouch、Marc Payard、Philippe R Loiseau、Christian Bories、Philippe M Loiseau、Philippe Gayral

  DOI：10.1016/0223-5234(89)90011-1

  日期：1989.5
• Synthesis and Biological Activity of Novel Symmetrical Bis-2-phenyliminothiazolidine Derivatives
  作者：Gang-Yue Li、Xu-Hong Qian、Sheng-Gang Yan、Jing-Nan Cui、Qing-Chun Huang、Rong Zhang、Feng-Yu Liu、Da-Wei Cui

  DOI：10.1080/10426500600865103

  日期：2006.12.1

  A series of novel symmetrical bis-2-phenyliminothiazolidine derivatives were designed and synthesized. The structures of all the title compounds were characterized by H-1 NMR and, in some cases, by C-13 NMR, IR, and high-resolution mass spectra. Herbicidal activities were examined, and some of these compounds showed selectively herbicidal activity against Triticum aestivum. The type of linker between the two 2-phenyliminothiazolidines was crucial for the biological activities.