3-(benzyloxycarbonyl)amino-1-ethoxycarbonyl-4H-pyrido[1,2-a]pyridin-4-one | 223717-85-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹嗪类
• 英文名称: 3-(benzyloxycarbonyl)amino-1-ethoxycarbonyl-4H-pyrido[1,2-a]pyridin-4-one
• 英文别名: 3-(benzyloxycarbonyl)amino-1-ethoxycarbonyl-4H-quinolizin-4-one；Ethyl 4-oxo-3-(phenylmethoxycarbonylamino)quinolizine-1-carboxylate
• CAS: 223717-85-9
• 化学式: C₂₀H₁₈N₂O₅
• 分子量: 366.373
• InChiKey: KQSNNPAGFPSSLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(benzyloxycarbonyl)amino-1-ethoxycarbonyl-4H-pyrido[1,2-a]pyridin-4-one 在 氢溴酸 、 碳酸氢钠 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 生成 3-[N-α-(D)-mannopyranosyl]amino-1-ethoxycarbonyl-4H-quinolizin-4-one
  参考文献：
  名称：

  Synthesis and Characterisation of Some New N-Glycosides Containing Substituted Pyridopyrimidinone, Pyrimidopyridazinone, Thiazolopyrimidinone and Quinolizin-4-one Moiety

  摘要：

  A series of new N-glycosides (D-glucosides, D-mannosides, L- and D-arabinosides, D-Xylosides and one D-galactoside) containing heterocyclic moiety have been prepared by reaction of the corresponding heterocyclic amines with pyranoses in boiling methanol. The structures of the prepared compounds have been studied by means of proton and carbon NMR spectroscopy. In the most cases the products existed in DMSO solution as the single anomers.

  DOI：

  10.3987/com-08-11414
• 作为产物：
  描述：

  CBZ-甘氨酸甲酯 以 溶剂黄146 、 甲苯 为溶剂， 反应 5.0h， 生成 3-(benzyloxycarbonyl)amino-1-ethoxycarbonyl-4H-pyrido[1,2-a]pyridin-4-one
  参考文献：
  名称：

  2-（苄氧基羰基）氨基-3-二甲基氨基丙烯酸甲酯的合成。三取代吡咯，3-氨基-2 H-吡喃-2-酮，稠合的2 H-吡喃-2-酮和4 H-吡啶-4-酮的合成

  摘要：

  由N-（苄氧基羰基）甘氨酸甲酯（1）和叔丁氧基双（二甲基氨基）甲烷制得2-（苄氧基羰基）亚氨基-3-二甲基氨基丙酸甲酯（2），并用作制备取代的3-（苄氧基羰基）的试剂。氨基-4- ħ喹嗪-4-酮5和6，-2 ħ吡喃-2-酮17-19，-2 ħ -1-苯并吡喃-2-酮28-31，和-naphthopyrans 32-35， - 2 H-吡喃并[3,2 - c ]吡啶-2,5-二酮46，-吡喃并- [4,3 - b ]吡喃-2,5-二酮47，-pyrano [3,2 - c ]苯并吡喃-2,5-二酮48，-pyrano [2,3 - c ] pyrazol -6-ones 49和50，-pyrano [2,3 - d ] pyrirnidin-7 -酮51层52的衍生物。在2与1,3-二酮的反应中，形成了三取代的吡咯14-16。选择性除去苄氧羰基的由猫alytic转移氢化用Pd / C在环己烯

  DOI：

  10.1002/jhet.5570360135

文献信息

• Catalytic hydrogenation of 3-benzyloxycarbonylaminoazino[1,2-<i>x</i>]-azin-4-ones. A facile access to 3-amino-6,7,8,9-tetrahydro-4<i>H</i>-pyrido[1,2-<i>a</i>]pyridin-4-ones and 3-Amino-6,7,8,9-tetrahydro-4<i>H</i>-azino[1,2-<i>x</i>]pyrimidin-4-ones
  作者：Simon Rečnik、Renata Toplak、Jurij Svete、Lucija Pizzioli、Branko Stanovnik

  DOI：10.1002/jhet.5570370420

  日期：2000.7

  By catalytic hydrogenation of 3-(benzyloxycarbonyl)amino-4H-pyrido[1,2-a]pyridin-4-ones 28 and 29, and azino[1,2-x]pyrimidin-4-ones 32–35, 41, and 42, partial saturation of the heterocyclic systems and removal of the benzyloxycarbonyl moiety was observed to give 3-amino-6,7,8,9-tetrahydro-4H-pyrido[1,2 a]pyridin-4-ones 30 and 31, and 3-amino-6,7,8,9-tetrahydro-4H-azino[1,2-x]pyrimidin-4-ones 36–39

  通过催化氢化3-（苄氧羰基）氨基-4 H-吡啶并[1,2- a ]吡啶-4-酮28和29，以及叠氮基[1,2 - x ]嘧啶-4-酮32-35，41，和42时，观察到杂环体系和除去苄氧羰基结构部分中的部分饱和，得到3-氨基-6,7,8,9-四氢-4- ħ -吡啶并[1,2一]吡啶-4-酮30和31和3-氨基-6,7,8,9-四氢-4 H-叠氮[1,2 - x ]嘧啶-4-酮36-39、43和44高产。该方法代表简单的两步合成，从杂环α-氨基化合物和（Z）-2-（苄氧基羰基）氨基-3-二甲基氨基丙酸甲酯开始，然后进行催化氢化。
• The synthesis of methyl 2-(benzyloxycarbonyl)amino-3-dimethylaminopropenoate. The synthesis of trisubstituted pyrroles, 3-amino-2<i>H</i>-pyran-2-ones, fused 2<i>H</i>-pyran-2-ones and 4<i>H</i>-pyridin-4-ones
  作者：Renata Toplak、Jurij Svete、Branko Stanovnik、Simona GoliČ Grdadolnik

  DOI：10.1002/jhet.5570360135

  日期：1999.1

  Methyl 2-(benzyloxycarbonyl)aimno-3-dimemylaminopropenoate (2) was prepared from methyl N-(benzyloxycarbonyl)glycinate (1) and t-butoxybis(dimethylamino)methane, and used as a reagent for preparation of substituted 3-(benzyloxycarbonyl)amino-4H-quinolizin-4-ones 5 and 6, −2H-pyran-2-ones 17–19, −2H-1-benzopyran-2-ones 28–31, and -naphthopyrans 32–35, −2H-pyrano[3,2-c]pyridine-2,5-dione 46, -pyrano-[4

  由N-（苄氧基羰基）甘氨酸甲酯（1）和叔丁氧基双（二甲基氨基）甲烷制得2-（苄氧基羰基）亚氨基-3-二甲基氨基丙酸甲酯（2），并用作制备取代的3-（苄氧基羰基）的试剂。氨基-4- ħ喹嗪-4-酮5和6，-2 ħ吡喃-2-酮17-19，-2 ħ -1-苯并吡喃-2-酮28-31，和-naphthopyrans 32-35， - 2 H-吡喃并[3,2 - c ]吡啶-2,5-二酮46，-吡喃并- [4,3 - b ]吡喃-2,5-二酮47，-pyrano [3,2 - c ]苯并吡喃-2,5-二酮48，-pyrano [2,3 - c ] pyrazol -6-ones 49和50，-pyrano [2,3 - d ] pyrirnidin-7 -酮51层52的衍生物。在2与1,3-二酮的反应中，形成了三取代的吡咯14-16。选择性除去苄氧羰基的由猫alytic转移氢化用Pd / C在环己烯
• Synthesis and Characterisation of Some New N-Glycosides Containing Substituted Pyridopyrimidinone, Pyrimidopyridazinone, Thiazolopyrimidinone and Quinolizin-4-one Moiety
  作者：Petr Simunek、Jurij Svete、Branko Stanovnik

  DOI：10.3987/com-08-11414

  日期：——

  A series of new N-glycosides (D-glucosides, D-mannosides, L- and D-arabinosides, D-Xylosides and one D-galactoside) containing heterocyclic moiety have been prepared by reaction of the corresponding heterocyclic amines with pyranoses in boiling methanol. The structures of the prepared compounds have been studied by means of proton and carbon NMR spectroscopy. In the most cases the products existed in DMSO solution as the single anomers.