2'-(2-methoxyphenyl)spiro[1,3-dioxolane-2,7'-3,4,6,8,9,9a-hexahydro-1H-pyrido[1,2-a]pyrazine] | 134334-48-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 2'-(2-methoxyphenyl)spiro[1,3-dioxolane-2,7'-3,4,6,8,9,9a-hexahydro-1H-pyrido[1,2-a]pyrazine]
• CAS: 134334-48-8
• 化学式: C₁₇H₂₄N₂O₃
• 分子量: 304.389
• InChiKey: MUAYVJIIOXKDPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  34.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2'-(2-methoxyphenyl)spiro[1,3-dioxolane-2,7'-3,4,6,8,9,9a-hexahydro-1H-pyrido[1,2-a]pyrazine] 在 盐酸 作用下， 反应 2.0h， 以65%的产率得到Hexahydro-2-(2-methoxyphenyl)-2H-pyrido<1,2-a>pyrazin-7(6H)-one
  参考文献：
  名称：

  Synthesis of 2,5-substituted piperidines and their bicyclic piperazine analogs: the 2,7-substituted octahydro-2H-pyrido[1,2-a]pyrazines

  摘要：

  Partial and complete reduction of the key compound 1-benzyl-5-(ethylenedioxy)-2-piperidinecarbonitrile (1) was applied to generate the corresponding aldehyde 2 and primary amine 3. These were transformed into bicyclic 7-(ethylenedioxy)-2(R)-octahydro-2H-pyrido[1,2-a]pyrazines 7 (R = H) and 15 (R = aryl) through the following sequence: (i) chloroacetylation of 3 and of arylamines derived from 2, (ii) cyclization to give the intermediate lactams 5 and 14, and (iii) reduction with LiAlH4. Deprotection of the N-aryl compounds 15 yielded the corresponding ketone model compounds 16. From amino acetal 7, a complementary ketone synthon 11 was prepared via N-benzylation and cleavage of the acetal group, providing a general route to piperidine-bridged analogues of 1,4-substituted piperazine drugs.

  DOI：

  10.1021/jo00017a036
• 作为产物：
  描述：

  1-Benzyl-5-(ethylenedioxy)-2-piperidinecarboxaldehyde 在 lithium aluminium tetrahydride 、 四丁基溴化铵 、 sodium cyanoborohydride 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 邻二氯苯 为溶剂， 反应 2.17h， 生成 2'-(2-methoxyphenyl)spiro[1,3-dioxolane-2,7'-3,4,6,8,9,9a-hexahydro-1H-pyrido[1,2-a]pyrazine]
  参考文献：
  名称：

  Synthesis of 2,5-substituted piperidines and their bicyclic piperazine analogs: the 2,7-substituted octahydro-2H-pyrido[1,2-a]pyrazines

  摘要：

  Partial and complete reduction of the key compound 1-benzyl-5-(ethylenedioxy)-2-piperidinecarbonitrile (1) was applied to generate the corresponding aldehyde 2 and primary amine 3. These were transformed into bicyclic 7-(ethylenedioxy)-2(R)-octahydro-2H-pyrido[1,2-a]pyrazines 7 (R = H) and 15 (R = aryl) through the following sequence: (i) chloroacetylation of 3 and of arylamines derived from 2, (ii) cyclization to give the intermediate lactams 5 and 14, and (iii) reduction with LiAlH4. Deprotection of the N-aryl compounds 15 yielded the corresponding ketone model compounds 16. From amino acetal 7, a complementary ketone synthon 11 was prepared via N-benzylation and cleavage of the acetal group, providing a general route to piperidine-bridged analogues of 1,4-substituted piperazine drugs.

  DOI：

  10.1021/jo00017a036