N-(5-氯-1,3-苯并恶唑-2-基)-1-(3-硝基苯基)甲亚胺 | 114424-80-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 中文名称: N-(5-氯-1,3-苯并恶唑-2-基)-1-(3-硝基苯基)甲亚胺
• 英文名称: 5-chloro-2-((m-nitrophenyl)methyleneimino)benzoxazole
• 英文别名: N-(5-Chloro-1,3-benzoxazol-2-yl)-1-(3-nitrophenyl)methanimine；N-(5-chloro-1,3-benzoxazol-2-yl)-1-(3-nitrophenyl)methanimine
• CAS: 114424-80-5
• 化学式: C₁₄H₈ClN₃O₃
• 分子量: 301.689
• InChiKey: CGOUTXROBYPCSU-UHFFFAOYSA-N

物化性质

• 沸点：
  477.5±51.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  无水蔡斯盐 、 N-(5-氯-1,3-苯并恶唑-2-基)-1-(3-硝基苯基)甲亚胺 在 ethanol 作用下， 以 二氯甲烷 为溶剂， 以80-95的产率得到trans-PtCl2(C2H4)(ClC6H3ONCNHCH(OCH2CH3)C6H4-3-NO2)
  参考文献：
  名称：

  Stable platinum(II) complexed α-aminoethers derived from benzimidazole and benzoxazole

  摘要：

  A series of Schiff base compounds derived from 2-aminobenzimidazole and 2-aminobenzoxazole react with Zeise's salt in CH2Cl2/ROH (R = CH3, CH2CH3, CH(CH3)2, CH2CH2OCH3) to form a series of relatively stable alpha-aminoether complexes with coordination to Pt(II) via the heterocyclic sp2 nitrogen. The complexes, trans-PtCl2(C2H4){2-N-(CH(OR)C6II4R1)benzimidazole} (4) (R1 - 3-NO2, R = CH3, CH2CH3, CH(CH3)2; R1 = 4-Cl, R = CH3) and trans-PtCl2(C2H4){2-N-(CH(OR)C6H4R1)benzoxazole} (5) (R1 = 3-NO2, R = CH3, CH2CH3, CH2CH2OCH3; R1 = 4-Cl, 4-OCH3, 4-H, R = CH3) arise through initial coordination of the heterocyclic sp2 nitrogen followed by attack of ROH on the pendant 2-N-benzylidene moiety at the Schiff base carbon. It is suggested that withdrawal of electron density through complexation facilitates alcohol attack. In the absence of complexation the reaction can be 20-30 times slower, A Pd(II) phosphine complex can achieve the same result. H-1 NMR spectroscopy, and specifically the chemical shift of the 'CH-N' moiety, provides an indication of the polarization due to complexation. The structure of one complex, 5c, R1 - 3-NO2, R - CH2CH2OCH3, was determined by X-ray diffraction. A prismatic crystal belonging to the space group P1BAR with the following characteristics; a - 10.024(3), b = 11.242(9), c = 13.158(3) angstrom, alpha = 96.07(3), beta = 107.01(2), gamma = 109.52(3)-degrees, V = 1302 angstrom 3, Z = 2, was used to determine the structure, which was refined to R = 0.044.

  DOI：

  10.1016/s0020-1693(00)80240-6

文献信息

• Albinati, Alberto; Arz, Christof; Pregosin, Paul S., Inorganic Chemistry, 1988, vol. 27, # 12, p. 2015 - 2016
  作者：Albinati, Alberto、Arz, Christof、Pregosin, Paul S.

  DOI：——

  日期：——
• Stable platinum(II) complexed α-aminoethers derived from benzimidazole and benzoxazole
  作者：A. Albinati、C. Arz、H. Berger、P.S. Pregosin

  DOI：10.1016/s0020-1693(00)80240-6

  日期：1991.12

  A series of Schiff base compounds derived from 2-aminobenzimidazole and 2-aminobenzoxazole react with Zeise's salt in CH2Cl2/ROH (R = CH3, CH2CH3, CH(CH3)2, CH2CH2OCH3) to form a series of relatively stable alpha-aminoether complexes with coordination to Pt(II) via the heterocyclic sp2 nitrogen. The complexes, trans-PtCl2(C2H4)2-N-(CH(OR)C6II4R1)benzimidazole} (4) (R1 - 3-NO2, R = CH3, CH2CH3, CH(CH3)2; R1 = 4-Cl, R = CH3) and trans-PtCl2(C2H4)2-N-(CH(OR)C6H4R1)benzoxazole} (5) (R1 = 3-NO2, R = CH3, CH2CH3, CH2CH2OCH3; R1 = 4-Cl, 4-OCH3, 4-H, R = CH3) arise through initial coordination of the heterocyclic sp2 nitrogen followed by attack of ROH on the pendant 2-N-benzylidene moiety at the Schiff base carbon. It is suggested that withdrawal of electron density through complexation facilitates alcohol attack. In the absence of complexation the reaction can be 20-30 times slower, A Pd(II) phosphine complex can achieve the same result. H-1 NMR spectroscopy, and specifically the chemical shift of the 'CH-N' moiety, provides an indication of the polarization due to complexation. The structure of one complex, 5c, R1 - 3-NO2, R - CH2CH2OCH3, was determined by X-ray diffraction. A prismatic crystal belonging to the space group P1BAR with the following characteristics; a - 10.024(3), b = 11.242(9), c = 13.158(3) angstrom, alpha = 96.07(3), beta = 107.01(2), gamma = 109.52(3)-degrees, V = 1302 angstrom 3, Z = 2, was used to determine the structure, which was refined to R = 0.044.