7-(Ethylenedioxy)octahydro-2H-pyrido<1,2-a>pyrazin-3-one | 134334-36-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 7-(Ethylenedioxy)octahydro-2H-pyrido<1,2-a>pyrazin-3-one
• 英文别名: 7-(Ethylenedioxy)octahydro-2H-pyrido[1,2-a]pyrazin-3-one；Hexahydrospiro[[1,3]dioxolane-2,7'-pyrido[1,2-a]pyrazin]-3'(2'H)-one；spiro[1,3-dioxolane-2,7'-2,4,6,8,9,9a-hexahydro-1H-pyrido[1,2-a]pyrazine]-3'-one
• CAS: 134334-36-4
• 化学式: C₁₀H₁₆N₂O₃
• 分子量: 212.249
• InChiKey: BCQASEOJGJAXNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  50.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-(Ethylenedioxy)octahydro-2H-pyrido<1,2-a>pyrazin-3-one 在 盐酸 、 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 2-Benzyloctahydro-2H-pyrido<1,2-a>pyrazin-7-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：

  7-苯基甲基-1,4-二噁-7-氮杂螺[4.5]癸烷-8-甲腈 在 lithium aluminium tetrahydride 、 四丁基溴化铵 作用下， 以 四氢呋喃 、 二氯甲烷 、 邻二氯苯 为溶剂， 反应 1.58h， 生成 7-(Ethylenedioxy)octahydro-2H-pyrido<1,2-a>pyrazin-3-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

文献信息

• Compernolle, Frans; Saleh, M.-Ashty; Toppet, Suzanne, Journal of Heterocyclic Chemistry, 1991, vol. 28, # 8, p. 1965 - 1969
  作者：Compernolle, Frans、Saleh, M.-Ashty、Toppet, Suzanne、Buysser, Wim De、Hoornaert, Georges

  DOI：——

  日期：——
• Synthesis of 2,5-substituted piperidines and their bicyclic piperazine analogs: the 2,7-substituted octahydro-2H-pyrido[1,2-a]pyrazines
  作者：Frans Compernolle、M. Ashty Saleh、Suzanne Toppet、Georges Hoornaert

  DOI：10.1021/jo00017a036

  日期：1991.8

  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.