2-oxo-1,2,3,4-tetrahydro-pyrido[1,2-a]pyrimidin-5-ylium chloride | 27058-60-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶并嘧啶类
• 英文名称: 2-oxo-1,2,3,4-tetrahydro-pyrido[1,2-a]pyrimidin-5-ylium chloride
• 英文别名: 2-oxo-1,2,3,4-tetrahydro-pyrido[1,2-a]pyrimidinylium; chloride；2-Oxo-1,2,3,4-tetrahydro-pyrido[1,2-a]pyrimidinylium; Chlorid；3,4-Dihydro-1H-2-oxo-pyrido<1,2-e>pyrimidin-5-ium-chlorid；3,4-dihydropyrido[1,2-a]pyrimidin-2-one;hydrochloride
• CAS: 27058-60-2
• 化学式: C₈H₉N₂O*Cl
• 分子量: 184.625
• InChiKey: GMENRWZALODZFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.68
• 重原子数：
  12.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  32.98
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  2-氨基吡啶 、 3-氯丙酸 以 乙腈 为溶剂， 反应 7.0h， 以78%的产率得到2-oxo-1,2,3,4-tetrahydro-pyrido[1,2-a]pyrimidin-5-ylium chloride
  参考文献：
  名称：

  Prototropic equilibrium between 1-H-2-oxo-pyrido[2,1-b][3,4]dihydropyrimidinium chloride and 3-(2-aminopyridinium)propionate hydrochloride studied by X-ray, FTIR, Raman, NMR and ab initio methods

  摘要：

  1-H-2-oxo-pyrido[2,1-b][3,4]dihydropyrimidinium chloride has been obtained from 2-amino-pyridine and 3-chloropropionic acid. The crystals are orthorhombic, space group Prima, with a = 7.7435(15) A, b = 9.0838(18) A, c = 12.676(3) A, V = 841.4(3) A(3) and Z = 3 (at 293(2) K). Two conformers are present in the crystal structure. The N(l) center dot center dot center dot Cl hydrogen bond length are 3.112(3) and 3.150(3) A, respectively. The vC=O at 1714 cm(-1) and the vNH band at 2660 cm(-1) in the FTIR spectrum agree well with the bicyclic structure of the molecule investigated. The tentative assignments for the experimental solid state FTIR spectrum have been made on the basis of B3LYP calculated frequencies.Two of the most stable conformers have been analyzed by the B3LYP and MP2 calculations. The energy barrier about the C(3)-C(4) bond between them is 1.7 kcal mol(-1). Correlations between the experimental H-1 and C-13 NMR chemical shifts (delta(exp)) and the GIAO/ BRYP/6-311++G(d,p) calculated magnetic isotropic shielding tensors (a,a,) for both conformers, delta(exp) = n + b sigma(cal), are reported. A good linear relationship between the experimental and the calculated data was obtained only for carbon atoms. In a DMSO solution containing traces of water, 1-H-2-oxo-pyrido[2,1-b][3,4]dihydropyrimidinium chloride exists in an equilibrium with 3-(2-amino-pyridinium)propionate hydrochloride. (c) 2008 Published by Elsevier B.V.

  DOI：

  10.1016/j.molstruc.2007.04.036

文献信息

• MUKAIYAMA TERUAKI; AIKAWA YUKIKO; KOBAYASHI SUSUMU, CHEM. LETT. 1976, NO 1, 57-60
  作者：MUKAIYAMA TERUAKI、 AIKAWA YUKIKO、 KOBAYASHI SUSUMU

  DOI：——

  日期：——
• Prototropic equilibrium between 1-H-2-oxo-pyrido[2,1-b][3,4]dihydropyrimidinium chloride and 3-(2-aminopyridinium)propionate hydrochloride studied by X-ray, FTIR, Raman, NMR and ab initio methods
  作者：M. Szafran、I. Kowalczyk、A. Katrusiak

  DOI：10.1016/j.molstruc.2007.04.036

  日期：2008.3

  1-H-2-oxo-pyrido[2,1-b][3,4]dihydropyrimidinium chloride has been obtained from 2-amino-pyridine and 3-chloropropionic acid. The crystals are orthorhombic, space group Prima, with a = 7.7435(15) A, b = 9.0838(18) A, c = 12.676(3) A, V = 841.4(3) A(3) and Z = 3 (at 293(2) K). Two conformers are present in the crystal structure. The N(l) center dot center dot center dot Cl hydrogen bond length are 3.112(3) and 3.150(3) A, respectively. The vC=O at 1714 cm(-1) and the vNH band at 2660 cm(-1) in the FTIR spectrum agree well with the bicyclic structure of the molecule investigated. The tentative assignments for the experimental solid state FTIR spectrum have been made on the basis of B3LYP calculated frequencies.Two of the most stable conformers have been analyzed by the B3LYP and MP2 calculations. The energy barrier about the C(3)-C(4) bond between them is 1.7 kcal mol(-1). Correlations between the experimental H-1 and C-13 NMR chemical shifts (delta(exp)) and the GIAO/ BRYP/6-311++G(d,p) calculated magnetic isotropic shielding tensors (a,a,) for both conformers, delta(exp) = n + b sigma(cal), are reported. A good linear relationship between the experimental and the calculated data was obtained only for carbon atoms. In a DMSO solution containing traces of water, 1-H-2-oxo-pyrido[2,1-b][3,4]dihydropyrimidinium chloride exists in an equilibrium with 3-(2-amino-pyridinium)propionate hydrochloride. (c) 2008 Published by Elsevier B.V.