N-(3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl)pyridine-2-aldimine | 237737-63-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: N-(3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl)pyridine-2-aldimine
• 英文别名: N-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-1-pyridin-2-ylmethanimine
• CAS: 237737-63-2
• 化学式: C₂₀H₂₆N₄O
• 分子量: 338.453
• InChiKey: VSKNDCMEBWRJHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  41
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [ReOCl₃(PPh₃)₂] 、 benzoyl(mercaptoacetyl)glycine 、 N-(3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl)pyridine-2-aldimine 在 NaOH 、 HCl 、 CH₃COONa 作用下， 以 甲醇 为溶剂， 以72%的产率得到ReO(N-(3-(4-(2-methoxyphenyl)piperazin-1-yl)propyl)pyridine-2-aldimine)(N-(2-mercaptoacetyl)glycine(-3H))
  参考文献：
  名称：

  Synthesis and Characterization of Novel “3 + 2” Oxorhenium Complexes, ReO[SNO][NN]

  摘要：

  The present paper deals with the synthesis and structural characterization of novel neutral oxorhenium(V) complexes of the general formula ReO[SNO][NN]. The simultaneous action of the tridentate SNO ligand, N-(2-mercaptoacetyl)glycine (1), and the bidentate NN ligand, N-phenylpyridine-2-aldimine (2), on ReOCl3(PPh3)(2) leads to the formation of two isomers 4a and 4b of the general formula ReO[SNO][NN], as a result of the different orientations of the NN ligand. In both cases, the SNO donor atoms of the tridentate ligand occupy the three positions in the equatorial plane of the distorted octahedron, whereas the oxo group is always directed toward one of the apical positions. In the first isomer, 4a, the imino nitrogen of the NN ligand occupies the fourth equatorial position and the pyridine type nitrogen is directed trans to the oxo group, while in the second isomer, 4b, the imino nitrogen of the NN ligand occupies the apical position trans to the oxo group and the pyridine type nitrogen completes the equatorial plane of the distorted octahedron. The [SNO][NN] mixed-ligand system was applied in the synthesis of the oxorhenium complex 5 in which the 1-(2-methoxyphenyl) piperazine moiety, a fragment of the true 5-HT1A antagonist WAY 100635, has been incorporated in the NN bidentate ligand (NN is N-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl}pyridine-2-aldimine). In this case, high-performance liquid chromatography and NMR showed the existence of one isomer, 5, in which the pyridine nitrogen is trans to the oxo core, as demonstrated by crystal structure analysis.

  DOI：

  10.1021/ic0604260

文献信息

• Synthesis and Characterization of Novel “3 + 2” Oxorhenium Complexes, ReO[SNO][NN]
  作者：Aris Chiotellis、Charalambos Tsoukalas、Maria Pelecanou、Apostolos Papadopoulos、Catherine Raptopoulou、Aris Terzis、Ioannis Pirmettis、Minas Papadopoulos、Efstratios Chiotellis

  DOI：10.1021/ic0604260

  日期：2006.7.1

  The present paper deals with the synthesis and structural characterization of novel neutral oxorhenium(V) complexes of the general formula ReO[SNO][NN]. The simultaneous action of the tridentate SNO ligand, N-(2-mercaptoacetyl)glycine (1), and the bidentate NN ligand, N-phenylpyridine-2-aldimine (2), on ReOCl3(PPh3)(2) leads to the formation of two isomers 4a and 4b of the general formula ReO[SNO][NN], as a result of the different orientations of the NN ligand. In both cases, the SNO donor atoms of the tridentate ligand occupy the three positions in the equatorial plane of the distorted octahedron, whereas the oxo group is always directed toward one of the apical positions. In the first isomer, 4a, the imino nitrogen of the NN ligand occupies the fourth equatorial position and the pyridine type nitrogen is directed trans to the oxo group, while in the second isomer, 4b, the imino nitrogen of the NN ligand occupies the apical position trans to the oxo group and the pyridine type nitrogen completes the equatorial plane of the distorted octahedron. The [SNO][NN] mixed-ligand system was applied in the synthesis of the oxorhenium complex 5 in which the 1-(2-methoxyphenyl) piperazine moiety, a fragment of the true 5-HT1A antagonist WAY 100635, has been incorporated in the NN bidentate ligand (NN is N-3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl}pyridine-2-aldimine). In this case, high-performance liquid chromatography and NMR showed the existence of one isomer, 5, in which the pyridine nitrogen is trans to the oxo core, as demonstrated by crystal structure analysis.