N,N'-phenylene-diylbis[3-(1-aminoethyl)-6-methyl-2H-pyran-2,4(3H)-dione]

• 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: N,N'-phenylene-diylbis[3-(1-aminoethyl)-6-methyl-2H-pyran-2,4(3H)-dione]
• 英文别名: (3E)-6-methyl-3-[1-[2-[[(1E)-1-(6-methyl-2,4-dioxopyran-3-ylidene)ethyl]amino]anilino]ethylidene]pyran-2,4-dione
• 化学式: C₂₂H₂₀N₂O₆
• 分子量: 408.411
• InChiKey: AOCAMYKTTCENHB-IWGRKNQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.12
• 重原子数：
  30.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  110.8
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  邻苯二胺 、 脱氢乙酸 以 甲醇 为溶剂， 反应 1.0h， 以52%的产率得到N,N'-phenylene-diylbis[3-(1-aminoethyl)-6-methyl-2H-pyran-2,4(3H)-dione]
  参考文献：
  名称：

  Molecular and crystal structures of N,N′-propylene- and N,N′-phenylene-diylbis [3-(1-aminoethyl)-6-methyl-2H-pyran-2,4(3H)-dione]

  摘要：

  Two macrocyclic ligands, N,N'-propylene-diylbis[3-(I-aminoethyl)-6-methyl-2H-pyran-2,4(3H)-dione] I and N,M-phenylene-diylbis[3(1-aminoethyl)-6-methyl-2H-pyran-2,4(3H)-dione] 11, have been prepared by the condensation of dehydroacetic acid (3-acetyl-4-hydroxy-6methyl-2H-pyran-2-one) with 1,2-phenylenediamine and 1,3-propylenediamine. They have been characterized by means of elemental analysis, IR spectroscopy as well as by X-ray crystallography. The molecular structures of the compounds I and 11 can be described as consisting of two beta-enaminone-2-pyrone rings interlaced with either alkyl chain in I or phenyl ring in II. The X-ray studies confirmed the existence of strong N-(HO)-O-... intramolecular hydrogen bonds in both structures. Their lengths are in accordance to lengths of RAHB intramolecular hydrogen bonds in 1,3-diketones, aryl-hydrazones, beta-enaminones and related heterodienes (2.5-2.6 angstrom) [P. Gilli, V. Bertolasi, V. Ferretti and G. Gilli, J. Am. Chem. Soc., 122 (2000) 10405]. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2005.04.024

文献信息

• Molecular and crystal structures of N,N′-propylene- and N,N′-phenylene-diylbis [3-(1-aminoethyl)-6-methyl-2H-pyran-2,4(3H)-dione]
  作者：Marina Cindrić、Tanja Kajfež Novak、Krunoslav Užarević

  DOI：10.1016/j.molstruc.2005.04.024

  日期：2005.8

  Two macrocyclic ligands, N,N'-propylene-diylbis[3-(I-aminoethyl)-6-methyl-2H-pyran-2,4(3H)-dione] I and N,M-phenylene-diylbis[3(1-aminoethyl)-6-methyl-2H-pyran-2,4(3H)-dione] 11, have been prepared by the condensation of dehydroacetic acid (3-acetyl-4-hydroxy-6methyl-2H-pyran-2-one) with 1,2-phenylenediamine and 1,3-propylenediamine. They have been characterized by means of elemental analysis, IR spectroscopy as well as by X-ray crystallography. The molecular structures of the compounds I and 11 can be described as consisting of two beta-enaminone-2-pyrone rings interlaced with either alkyl chain in I or phenyl ring in II. The X-ray studies confirmed the existence of strong N-(HO)-O-... intramolecular hydrogen bonds in both structures. Their lengths are in accordance to lengths of RAHB intramolecular hydrogen bonds in 1,3-diketones, aryl-hydrazones, beta-enaminones and related heterodienes (2.5-2.6 angstrom) [P. Gilli, V. Bertolasi, V. Ferretti and G. Gilli, J. Am. Chem. Soc., 122 (2000) 10405]. (c) 2005 Elsevier B.V. All rights reserved.