5-methyl-7-phenyl-1,8-naphthyridin-2-one | 168099-73-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-methyl-7-phenyl-1,8-naphthyridin-2-one
• 英文别名: 5-methyl-7-phenyl-1,8-naphthrydin-2-one；5-methyl-7-phenyl-1H-1,8-naphthyridin-2-one
• CAS: 168099-73-8
• 化学式: C₁₅H₁₂N₂O
• 分子量: 236.273
• InChiKey: ISQMWEOZFWQJFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  氯化铑(三水) 、 5-methyl-7-phenyl-1,8-naphthyridin-2-one 在 NaOMe 作用下， 以 甲醇 为溶剂， 以87%的产率得到
  参考文献：
  名称：

  Dinuclear Rh(I,I) and Rh(II,II) complexes containing bridging asymmetrically 2,7-disubstituted naphthyridines

  摘要：

  The dirhodium(I) complex cis-[Rh-2(mphonp)(2)(CO)(4)] (1) was prepared by reaction of 5-methyl-7-phenyl-1,8-naphthyridin-2-one (Hmphonp) with [{RhCl(CO)(2)}(2)] in methanol in the presence of base (NaOMe). The mphonp(-) ligands adopt a head-tail orientation relative to one another and bridge the Rh(I) atoms in the O2,N1 coordination mode. Treatment of RhCl3 . 3H(2)O with mphonp(-) in methanol affords the dirhodium(II) complex [Rh-2(mphonp)(4)] (2) in which cyclometalation leads to a novel chelating N8,C72 mode by two of the naphthyridine ligands. The Rh(II) atoms are bridged by the remaining mphonp(-) ligands with the O2,N1 coordination pattern being supplemented by N-8 as an axial donor atom. This mode requires a pronounced tilting of the bridging ligands towards the Rh-Rh axis leading to very long Rh-O2 distances (av. 2.30(2) Angstrom) and wide Rh-N1-C2 angles (av. 133(2)degrees). The Rh-Rh distances are 2.883(4) and 2.566(3) Angstrom in complexes 1 and 2, respectively (X-ray analyses).

  DOI：

  10.1016/s0020-1693(96)05147-x

文献信息

• <i>cis</i> ‐ and <i>trans</i> ‐Dimolybdenum(II) Complexes with Asymmetrically 2,7‐Disubstituted Naphthyridines as Bridging Ligands
  作者：Markus Mintert、William S. Sheldrick

  DOI：10.1002/cber.19961290615

  日期：1996.6

  Treatment of [Mo(CO)6] with Hmamnp (2-acetamido-7-methyl-1,8-naphthyridine) in diglyme at 100°C affords the mononuclear complex [Mo(CO)4(Hmamnp)] 1, an intermediate product on the reaction pathway to tetrasubstituted species of the type [Mo2L4]. A disubstituted intermediate product cis-[Mo2(mphamnp)2(OAc)2] 2 (Hmphamnp) (2-acetamido-5-methyl-7-phenyl-1,8-naphthyridine) may be isolated from the reaction

  在100°C下用二甘醇二甲醚用Hmamnp（2-乙酰氨基-7-甲基-1,8-萘啶）处理[Mo（CO）6 ]，得到单核络合物[Mo（CO）4（Hmamnp）] 1，一种中间体在反应路径上生成[Mo 2 L 4 ]型四取代物质的产物。可以从[Mo]的反应中分离出双取代的中间产物顺式-[Mo 2（mphamnp）2（OAc）2 ] 2（Hmphamnp）（2-乙酰氨基-5-甲基-7-苯基-1,8-萘啶）2（OAc）4 ]与mphamnp –在THF中。这种产物的相对稳定是共平面2-乙酰氨基取代基的空间需求的结果。2和四取代的配合物反式-[Mo 2（mbznnp）4 ] 3（Hmbznnp = 2-苄氨基-7-甲基-1,8-萘啶），顺式-[Mo 2（mphonp）4 ] 4和反式-[沫2（mphonp）4 ] 5（Hmphonp = 5-甲基-7-苯基-1,8-萘啶-2-酮）都表现出该电子者优先μ-N
• Di- and linear tri-nuclear carbonyl ruthenium clusters containing asymmetrically bridging 2,7-disubstituted naphthyridines
  作者：Markus Mintert、William S. Sheldrick

  DOI：10.1039/dt9950002663

  日期：——

  The diruthenium(I) complex cis- [Ru-2(bmnapy)(2)(CO)(4)] 1 was prepared by reaction of 2-benzylamino-7-methyl-1 ,8-naphthyridine (Hbmnapy) with [Ru-3(CO)(12)] in benzene. The N-1,N-2 co-ordination mode of the bridging ligands is supplemented by N-8 as an axial donor atom. In contrast, the analogous reaction with 7-methyl-1,8-naphthyridin-2-one (Hmonapy) or the corresponding 5-methyl-7-phenyl derivative (Hmopnapy) afforded the respective trinuclear clusters cis- [Ru-3(monapy)(2)(CO)(6)] 2 and cis[Ru-3(mopnapy)(2)(CO)(6)] 3, which exhibit three-atom chains with 46 valence electrons. X-Ray structural analyses demonstrate that the Ru-Ru bond distance remains effectively unchanged on going from the Ru-2 unit in 1 [2.707(1) Angstrom] to the Ru-3 sequence in 3 [average 2.701(2) Angstrom], for which an Ru-Ru-Ru angle of 168.6(3)degrees is observed.
• Diruthenium complexes with 5-methyl-7-phenyl-1,8-naphthyridin-2-one as an ambidentate bridging ligand
  作者：Markus Mintert、William S. Sheldrick

  DOI：10.1016/0020-1693(95)04489-v

  日期：1995.8

  Reaction of [Ru2Cl(OAc)(4)] with mphonp(-) (Hmphonp = 5-methyl-7-phenyl-1,8-naphthyridin-2-one) in methanol at reflux leads to precipitation of the diruthenium(II,III) complex [Ru2Cl(mphonp)(2)(OAc)(2)] (1) within 0.5 h. The compound exhibits a polar arrangement of ligands with Ru(1) coordinated by two trans-sited mphonp N1 atoms, Ru(2) by two trans-sited mphonp O2 atoms and the axial chloride ligand. 1 is reduced to the diruthenium(II,II) complex [Ru-2(mphonp)(2)(OAc)(2)] (2) on further refluxing (6 h). In contrast to 1, the trans-sited mphonp(-) ligands now display the N,N' coordination mode and point in opposite directions. The further reaction of 2 with mphonp(-) in refluxing methanol (36 h) then leads to substitution of all four acetate ligands and the formation of [Ru-2(mphonp)(4)] (3a). Steric interactions between adjacent phenyl substituents appear to be responsible for the adoption of the electronically less preferred N,O coordination mode by three of the bridging ligands in the polar water adduct [Ru-2(mphonp)(4)(H2O)] (3b). Hmphonp, 1, 2 and 3b were characterised by X-ray structural analysis.