2-propylamino-5-(4-aminophenyl)-1,3,4-thiadiazole | 106346-54-7

• 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: 2-propylamino-5-(4-aminophenyl)-1,3,4-thiadiazole
• 英文别名: 1,3,4-Thiadiazol-2-amine, 5-(4-aminophenyl)-N-propyl-；5-(4-aminophenyl)-N-propyl-1,3,4-thiadiazol-2-amine
• CAS: 106346-54-7
• 化学式: C₁₁H₁₄N₄S
• 分子量: 234.325
• InChiKey: NHVPAORNOUSLOJ-UHFFFAOYSA-N

物化性质

• 沸点：
  416.5±47.0 °C(Predicted)
• 密度：
  1.263±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  92.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-propylamino-5-(4-aminophenyl)-1,3,4-thiadiazole 、 3,5-二氯水杨醛 以 甲醇 为溶剂， 以68%的产率得到2-propylamino-5-[4-(2-hydroxy-3,5-dichlorobenzylideneamino)phenyl]-1,3,4-thiadiazole
  参考文献：
  名称：

  2-Propylamino-5-[4-(2-hydroxy-3,5-dichlorobenzylideneamino) phenyl]-1,3,4-thiadiazole: X-ray and DFT-calculated structures

  摘要：

  2-丙基氨基-5-[4-(2-羟基-3,5-二氯苄叉氨基)苯基]-1,3,4-噻二唑（I）被合成。（I）的晶体和分子结构通过1H-NMR、IR和X射线单晶衍射测定。化合物（I）在单斜晶系中结晶，空间群为P2(1)/c，晶胞参数为a=9.0576(2)Å、b=24.3382(8)Å、c=9.0585(2)Å、M r=407.31、V=1851.13(9)Å3、Z=4、R 1=0.036和wR 2=0.096。使用密度泛函方法（B3LYP）和6-31G(d)基组对（I）在基态下的X射线实验的分子几何结构进行了比较。为了确定构象的灵活性，通过半经验（PM3）计算获得了（I）的分子能量分布，其中选择的扭转自由度从-180°到+180°，以10°为步长。结果表明，含有噻二唑环的席夫碱更倾向于处于E构象

  DOI：

  10.1007/s11224-009-9523-z
• 作为产物：
  描述：

  4-(苯甲酰基氨基)苯甲酸乙酯 在 硫酸 、 一水合肼 作用下， 生成 2-propylamino-5-(4-aminophenyl)-1,3,4-thiadiazole
  参考文献：
  名称：

  Synthesis and antituberculosis activity of new N-phenyl-N′-[4-(5-alkyl/arylamino-1,3,4-thiadiazole-2-yl)phenyl]thioureas

  摘要：

  In this study, eight original N-phenyl-N'-[4-(5-alkyl/arylamino-1,3,4-thiadiazole-2-yl)phenyl]thiourea, derivatives were synthesized and tested for antituberculosis activity. Antituberculosis activities of the synthesized compounds were screened in vitro using BACTEC 460 Radiometric System against Mycobacterium tuberculosis H37Rv at 6.25 mug/ml. The highest inhibition observed with the synthesized compounds is 67% for N-phenyl-N'-[4-(5-cyclohexylamino-1,3,4-thiadiazole-2-yl)phenyl]thiourea. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0014-827x(02)01252-1

文献信息

• Synthesis and antituberculosis activity of new N-phenyl-N′-[4-(5-alkyl/arylamino-1,3,4-thiadiazole-2-yl)phenyl]thioureas
  作者：S. Karakuş、S. Rollas

  DOI：10.1016/s0014-827x(02)01252-1

  日期：2002.7

  In this study, eight original N-phenyl-N'-[4-(5-alkyl/arylamino-1,3,4-thiadiazole-2-yl)phenyl]thiourea, derivatives were synthesized and tested for antituberculosis activity. Antituberculosis activities of the synthesized compounds were screened in vitro using BACTEC 460 Radiometric System against Mycobacterium tuberculosis H37Rv at 6.25 mug/ml. The highest inhibition observed with the synthesized compounds is 67% for N-phenyl-N'-[4-(5-cyclohexylamino-1,3,4-thiadiazole-2-yl)phenyl]thiourea. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.
• 2-Propylamino-5-[4-(2-hydroxy-3,5-dichlorobenzylideneamino) phenyl]-1,3,4-thiadiazole: X-ray and DFT-calculated structures
  作者：Nevin Süleymanoğlu、Reşat Ustabaş、Yelda Bingöl Alpaslan、Ufuk Çoruh、Sevgi Karakuş、Sevim Rollas

  DOI：10.1007/s11224-009-9523-z

  日期：2010.2

  2-Propylamino-5-[4-(2-hydroxy-3,5-dichlorobenzylideneamino) phenyl]-1,3,4-thiadiazole, formulated as C18H16Cl2N4OS (I), was synthesized. The crystal and molecular structure of (I) have been determined by 1H-NMR, IR, and X-ray single crystal diffraction. The compound (I) crystallizes in the monoclinic, space group P2(1)/c with unit cell parameters a = 9.0576(2) Å, b = 24.3382(8) Å, c = 9.0585(2) Å, M r = 407.31, V = 1851.13(9) Å3, Z = 4, R 1 = 0.036, and wR 2 = 0.096. Molecular geometry from X-ray experiment of (I) in the ground state has been compared using the density functional method (B3LYP) with 6-31G(d) basis set. To determine conformational flexibility, molecular energy profile of (I) was obtained by semi-empirical (PM3) calculations with respect to selected degree of torsional freedom, which was varied from −180° to +180° in steps of 10°. The results are indicative that the Schiff base, which contains a thiadiazole ring, prefers to be in E-configuration. In addition, molecular electrostatic potential, frontier molecular orbitals, and natural bond orbitals analysis were performed by the B3LYP/6-31G(d) method.

  2-丙基氨基-5-[4-(2-羟基-3,5-二氯苄叉氨基)苯基]-1,3,4-噻二唑（I）被合成。（I）的晶体和分子结构通过1H-NMR、IR和X射线单晶衍射测定。化合物（I）在单斜晶系中结晶，空间群为P2(1)/c，晶胞参数为a=9.0576(2)Å、b=24.3382(8)Å、c=9.0585(2)Å、M r=407.31、V=1851.13(9)Å3、Z=4、R 1=0.036和wR 2=0.096。使用密度泛函方法（B3LYP）和6-31G(d)基组对（I）在基态下的X射线实验的分子几何结构进行了比较。为了确定构象的灵活性，通过半经验（PM3）计算获得了（I）的分子能量分布，其中选择的扭转自由度从-180°到+180°，以10°为步长。结果表明，含有噻二唑环的席夫碱更倾向于处于E构象