1,1,3-trimethyl-3-(2-(1,3,3-trimethylthioureido)ethyl)thiourea | 202073-21-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫脲类
• 英文名称: 1,1,3-trimethyl-3-(2-(1,3,3-trimethylthioureido)ethyl)thiourea
• 英文别名: 1-[2-[Dimethylcarbamothioyl(methyl)amino]ethyl]-1,3,3-trimethylthiourea
• CAS: 202073-21-0
• 化学式: C₁₀H₂₂N₄S₂
• 分子量: 262.443
• InChiKey: WUIYRXROEFFDEJ-UHFFFAOYSA-N

物化性质

• 沸点：
  482.2±28.0 °C(Predicted)
• 密度：
  1.128±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  77.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  乙二胺氯化铂(II) 、 1,1,3-trimethyl-3-(2-(1,3,3-trimethylthioureido)ethyl)thiourea 、 silver nitrate 以 N,N-二甲基甲酰胺 为溶剂， 以34%的产率得到bis[chloro(1,2-ethanediamine-κ(2)N,N')platinum(II)]-μ-[1,1,3-trimethyl-3-(2-(1,3,3-trimethylthioureido)ethyl)thiourea-.kappa(2)S,S'](2+) dinitrate
  参考文献：
  名称：

  Modification of Platinum(II) Antitumor Complexes with Sulfur Ligands. 1. Synthesis, Structure, and Spectroscopic Properties of Cationic Complexes of the Types [PtCl(diamine)(L)]NO₃ and [{PtCl(diamine)}₂(L-L)](NO₃)₂ (L = Monofunctional Thiourea Derivative; L-L = Bifunctional Thiourea Derivative)

  摘要：

  A new class of mono-and dinuclear platinum(II) complexes is described that derives from the cisplatin analogues (Pt(en)Cl-2] and [Pt(dach)Cl-2] (en = 1,2-ethanediamine, dach = racemic trans-1,2-cyclohexanediamine). The selective substitution of one chloro ligand in these species by 1,1,3,3-tetramethylthiourea (tmtu), which requires abstraction of chloride with silver salt in DMF, gives [PtCl(en)(tmtu)]NO3 (1) and [PtCl(dach)(tmtu)]NO3 (2). Similarly, reactions employing the novel bifunctional thiourea derivatives C2H4(NMeCSNMe2)(2) (3) and C6H12-(NMeCSNMe2)(2) (4) yield the dinuclear complexes [{Pt(en)Cl}(2)(mu-3-S,S')](NO3)(2) (5) and [{Pt(en)Cl}(2)(mu-4-S,S')]-(NO3)(2) . 0.5EtOH (6), respectively. The compounds were characterized by H-1, C-13, and Pt-195 Nh IR spectroscopy, elemental analyses, and IR data, Pt-195 chemical shifts in the -2895 to -2929 ppm region confirm the mixed-donor [PtN2ClS] coordination for 1, 2, 5, and 6 and thiourea-S coordination in all cases, The single-crystal X-ray structures of 2-4 have been determined. 2: monoclinic, space group P2(1)/n, a = 10.804 Angstrom, b = 16.221 Angstrom, c = 21.789 Angstrom, beta = 102.16(1)degrees, Z = 8. 3: monoclinic, space group P2(1)/n, a = 12.787(2) Angstrom, b = 6.250(1) Angstrom, c = 17.777(3) Angstrom, beta = 98.21(1)degrees, Z = 4. 4: monoclinic, space group P2(1)/n, a = 11.097(3) Angstrom, b = 13.717 Angstrom, c = 11.925 Angstrom, beta = 97.61(2)degrees, Z = 4. The Pt-S distance in 2 (2.285(2) Angstrom, mean) is in accordance with the magnitude of shielding found for the Pt-195 core and suggests weak pi-acceptor properties of tmtu. The bifunctional thiourea derivatives 3 and 4 adopt highly elongated conformations in the solid state where the sulfur atoms and the n-(CH2)(n), (n = 2, 6) linkers are Z-oriented. Force field calculations on 3 and 1 imply that the Z-form should be the prefer-red conformer for the thiourea groups in solution, H-1 NMR spectra indicate a dynamic equilibrium of different rotamers due to low barriers of rotation within the thiourea moieties in free and coordinated 3 and 4. It is suggested that the steric and electronic effects of the peralkylated thiourea derivatives in 1, 2, 5, and 6 may modulate the affinity of the complexes for biomolecules.

  DOI：

  10.1021/ic970420y