6-甲基-6,7,8,9-四氢吡啶并[6,1-b]嘧啶-4-酮 | 32092-29-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶并嘧啶类
• 中文名称: 6-甲基-6,7,8,9-四氢吡啶并[6,1-b]嘧啶-4-酮
• 英文名称: 6-methyl-6,7,8,9-tetrahydro-4H-pyrido<1,2-a>pyrimidin-4-one
• 英文别名: 6-methyl-6,7,8,9-tetrahydro-pyrido[1,2-a]pyrimidin-4-one；6-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine；4H-Pyrido[1,2-a]pyrimidin-4-one, 6,7,8,9-tetrahydro-6-methyl-；6-methyl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one
• CAS: 32092-29-8
• 化学式: C₉H₁₂N₂O
• 分子量: 164.207
• InChiKey: HCJOGZBBWGQKGC-UHFFFAOYSA-N

物化性质

• 沸点：
  262.9±23.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)
• 保留指数：
  1578

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  6-甲基-6,7,8,9-四氢吡啶并[6,1-b]嘧啶-4-酮 在 sodium tetrahydroborate 作用下， 以 水 为溶剂， 反应 2.0h， 以0.9 g的产率得到6-methylperhydropyrido<1,2-a>pyrimidin-4-one
  参考文献：
  名称：

  Nitrogen bridgehead compounds. 26. Synthesis and stereochemistry of 3-phenylperhydropyrido[1,2-a]pyrimidin-4-ones

  摘要：

  DOI：

  10.1021/jo00145a038
• 作为产物：
  描述：

  6-methyl-4-oxo-1,6,7,8-tetrahydropyrido[1,2-a]pyrimidine-9-carbaldehyde 、 盐酸 、 sodium hydroxide 生成 6-甲基-6,7,8,9-四氢吡啶并[6,1-b]嘧啶-4-酮
  参考文献：
  名称：

  HORVATH, A.;HERMECZ, I.;VASVARI-DEBRECZY, L.;SIMON, K.;PNGOR-CSAKVARI, M.+, J. CHEM. SOC. PERKIN TRANS., 1983, N 2, 369-377

  摘要：

  DOI：

文献信息

• Nitrogen bridgehead compounds. Part 18. New antiallergic 4H-pyrido[1,2-a]pyrimidin-4-ones. Part I
  作者：Istvan Hermecz、Tibor Breining、Zoltan Meszaros、Agnes Horvath、Lelle Vasvari-Debreczy、Franz Dessy、Christine DeVos、Ludovic Rodriquez

  DOI：10.1021/jm00352a008

  日期：1982.10

  A new type of antiallergic agent, 9-hydrazono-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-ones, was synthesized and evaluated for inhibitory effects in the rat reagenic passive cutaneous anaphylaxis (PCA) screen. Several racemic 6-methyl derivatives were found to be more potent than disodium chromoglycate intravenously and some were also active orally. Structure-activity relationships are discussed

  合成了一种新型的抗过敏药9-肼基-6,7,8,9-四氢-4H-吡啶并[1,2-a]嘧啶-4-酮，并评估了其对大鼠自发性被动皮肤的抑制作用。过敏反应（PCA）屏幕。已发现几种消旋的6-甲基衍生物在静脉内比色甘氨酸二钠更有效，有些还具有口服活性。讨论了构效关系。在具有6S和6R绝对构型的对映异构体之间的6-甲基系列中观察到高立体特异性，前者更具活性。化合物17，（+）-6（S）-甲基-9-（苯肼基）-4-氧代-4H-吡啶并[1,2-a]嘧啶-3-羧酸[Chinoin-1045; [UCB L140]，ED50值为1.0 mumol / kg po，目前正在临床研究中。
• Substituted-4-oxo-1,6,7,8-tetrahydro-4H-pyrido[1,2-a]pyrimidines
  申请人：Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Rt.

  公开号：US04321377A1

  公开（公告）日：1982-03-23

  Nitrogen bridgehead compounds (pyrido-[1,2-a]-pyrimidine derivatives) which are useful intermediates in the making of known compounds of this class and which themselves possess PG-antagonist, analgesic, antiartheriosclerotic, tranquilizing and like pharmaceutical activity.

  氮桥头化合物（吡啶并[1,2-a]-嘧啶衍生物）是这一类已知化合物制备中有用的中间体，它们本身具有PG-拮抗剂、镇痛剂、抗动脉粥样硬化、镇静等药理活性。
• 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
• Structural studies on 6-methyl-9-carbamoyl-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-ones by1H,13C and15N NMR spectroscopy
  作者：Gábor Tóth、Carlos de La Cruz、István Bitter、István Hermecz、Béla Pete、Zoltán Mészáros

  DOI：10.1002/mrc.1270200408

  日期：1982.12

  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.
• 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：——

表征谱图