2,6-dimethyl-3-ethyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine | 70381-46-3

• 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: 2,6-dimethyl-3-ethyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine
• 英文别名: 2,6-dimethyl-3-ethyl-6,7,8,9-tetrahydro-4H-pyrido<1,2-a>pyrimidin-4-one；3-ethyl-2,6-dimethyl-6,7,8,9-tetrahydro-pyrido[1,2-a]pyrimidin-4-one；3-ethyl-2,6-dimethyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one；2,6-dimethyl-3-ethyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido(1,2-a)pyrimidine；2,6-Dimethyl-3-ethyl-6,7,8,9-tetrahydro-4H-pyrido<1,2-a>pyrimidin-4-on；3-ethyl-2,6-dimethyl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one
• CAS: 70381-46-3
• 化学式: C₁₂H₁₈N₂O
• 分子量: 206.288
• InChiKey: YKGILRCXDDGIMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,6-dimethyl-3-ethyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine 在 丙酮 作用下， 以 氯仿 为溶剂， 反应 3.0h， 生成 (6S,9S)-3-Ethyl-2,6-dimethyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-9-carboxylic acid dimethylamide
  参考文献：
  名称：

  Structural studies on 6-methyl-9-carbamoyl-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-ones by1H,13C and15N NMR spectroscopy

  摘要：

  AbstractSeveral 6‐methyl‐9‐carbamoyltetrahydro‐4H‐pyrido[1,2‐α]pyrimidin‐4‐ones have been prepared using phosgene iminium chloride. These compounds can exist in equilibrium as the cis (3A) imine ⇌ (3B) enamine ⇌ trans (3C) imine. 1H, 13C and 15N NMR prove that the cis‐ and trans‐imine isomers are predominant in the equilibrium. 1H NMR data reveal that the share of the 3B enamine form is negligible at measurable concentrations. The isomeric ratio 3A:3C is time dependent and can be monitored by measuring the CH3C‐6 and (CH3)2N signals. The 13C NMR data show that doublets in the range 42–45 ppm for C‐9 are only compatible with the imine forms 3A and 3C. The SCS values of the CH3C‐6 and OCN(CH3)2 groups were calculated and used for identification of the cis and trans isomers. 15N NMR data show that the N‐1 chemical shift of the imine is approximately − 140 ppm for compound 3, whereas that of a fixed enamine is around − 267.8. This provides additional support for the predominance of the imine tautomers in the equilibrium 3A ⇌ 3B ⇌ 3C. 15N data allow the stereoisomers 3A and 3C to be distinguished.

  DOI：

  10.1002/mrc.1270200408
• 作为产物：
  描述：

  2,6-二甲基-3-乙基-4-氧代-4H-吡啶并(1,2-a)嘧啶盐酸盐 在 镍 、 乙醇 、 氢气 作用下， 以 乙醇 为溶剂， 反应 7.0h， 以(99.5%) of 2,6-dimethyl-3-ethyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido(1,2-a)pyrimidine are obtained as a pale-yellow non-crystallizing oil, which的产率得到2,6-dimethyl-3-ethyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine
  参考文献：
  名称：

  Pyrido[1,2-A]pyrimidine derivatives and method of analgesic treatment

  摘要：

  公式为##STR1##或其药物可接受的酸加成物或季铵盐，其中R为羟基、羧基、较低的烷氧羰基、苄氧羰基、苯氧羰基、氨基甲酰基、N-较低烷基氨基甲酰基、N,N-二较低烷基氨基甲酰基、羧酰肼基、羧肼基或氰基；R.sup.2为C.sub.1到C.sub.6烷基；R.sup.3为C.sub.1到C.sub.6烷基或苄基；R.sup.4为单电子对、氢或较低烷基；虚线代表饱和或不饱和键，具有镇痛作用。

  公开号：

  US04291036A1

文献信息

• Nitrogen bridgehead compounds. Part 86. Synthesis and reactivity of 7,12-dihydropyrimido[1′,2′;1,2]pyrido[3,4-<i>b</i>]indol-4(6<i>H</i>)-ones. Debenzologues of rutaecarpine alkaloids
  作者：István Hermecz、PÉter Forgó、Zsolt Böcskei、Miklós Fehér、József Kökösi、György Szász

  DOI：10.1002/jhet.5570330344

  日期：1996.5

  of 7,12-dihydropyrimido[1′2′:1,2]pyrido[3,4-b]mdole-4(6H)-ones was prepared by Fischer indolization of 9-arylhydrazono-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrirmdin-4-ones. Quantum chemical calculations (ab initio and AM1) indicate that position 3 of 7,12-dihydropyrimido[1′,2′:1,2]pyrido-[3,4-b]indole-4(6H)-one can be involved in electrophilic substitutions, while position 2 is sensitive towards nucleophilic

  通过9-芳基肼基-6,7,8的费歇尔吲哚化制备了一系列7,12-二氢嘧啶基[1'2'：1,2]吡啶基[3,4- b ] mdole-4（6 H）-ones。 ，9-四氢-4 H-吡啶并[1,2 - a ]嘧啶-4-酮。量子化学计算（从头算和AM1）表明7,12-二氢嘧啶基[1'，2'：1,2]吡啶-[3,4- b ]吲哚-4（6 H）-的一个位置3参与亲电取代，而位置2对亲核攻击敏感。6-甲基-7,12-四氢嘧啶的溴化[1'，2'：1,2]吡啶并[3,4- b ]吲哚-4-（6 ħ） -酮16与溴，得到3-溴衍生物25，它与环胺反应生成2-AMmo-7,12-dihydropyrirmdo [1'2'：1,2] pyrido [3,4- b ] indol -4（6 H）-ones 26-30。加成消除反应。化合物16的Vielsmeier-Haack甲酰化分别在60°和100°下得到12-甲酰基31和3
• Pyrido[1,2-a]pyrimidine derivatives
  申请人：Chinoin Gyogyszer es Vegyeszeti Termekek Gyara RT

  公开号：US04219649A1

  公开（公告）日：1980-08-26

  Compounds of the formula: ##STR1## or pharmaceutically acceptable acid addition or quaternary ammonium salts thereof wherein R.sup.2 is C.sub.1 to C.sub.6 alkyl: R.sup.3 is C.sub.1 to C.sub.6 alkyl; R.sup.4 is a single electron pair, hydrogen or lower alkyl; and the dotted lines indicate saturated or unsaturated bonds, are disclosed with analgesic properties.

  公式为：##STR1## 或其药用可接受的酸盐或季铵盐，其中R.sup.2是C.sub.1到C.sub.6烷基；R.sup.3是C.sub.1到C.sub.6烷基；R.sup.4是一个单电子对、氢或较低烷基；虚线表示饱和或不饱和键，具有镇痛性能的化合物已被披露。
• Horvath, Agnes; Hermecz, Istvan; Vasvari-Debreczy, Lelle, Journal of the Chemical Society. Perkin transactions I, 1983, # 2, p. 369 - 378
  作者：Horvath, Agnes、Hermecz, Istvan、Vasvari-Debreczy, Lelle、Simon, Kalman、Pongor-Csakvari, Marianne、et al.

  DOI：——

  日期：——
• FUELOEP F.; HERMECZ I.; MESZAROS Z.; DOMBI G.; BERNATH G., J. HETEROCYCL. CHEM., 1979, 16, NO 3, 457-460
  作者：FUELOEP F.、 HERMECZ I.、 MESZAROS Z.、 DOMBI G.、 BERNATH G.

  DOI：——

  日期：——
• ACS, MARIA;HERMECZ, ISTVAN;FOGARASSY, ELEMER;HORVATH, AGNES;VASVARINE, DE+
  作者：ACS, MARIA、HERMECZ, ISTVAN、FOGARASSY, ELEMER、HORVATH, AGNES、VASVARINE, DE+

  DOI：——

  日期：——