Hexahydro-2H,6H-spiro[pyrido[1,2-a]pyrazine-7,2'-[1,3]dioxolane] | 134334-37-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Hexahydro-2H,6H-spiro[pyrido[1,2-a]pyrazine-7,2'-[1,3]dioxolane]
• 英文别名: spiro[1,2,3,4,6,8,9,9a-octahydropyrido[1,2-a]pyrazine-7,2'-1,3-dioxolane]
• CAS: 134334-37-5
• 化学式: C₁₀H₁₈N₂O₂
• 分子量: 198.265
• InChiKey: OJGLRWRFKZUWKR-UHFFFAOYSA-N

物化性质

• 沸点：
  316.6±42.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  33.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Hexahydro-2H,6H-spiro[pyrido[1,2-a]pyrazine-7,2'-[1,3]dioxolane] 在 盐酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 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：

  N-[(9-benzyl-1,4-dioxa-9-azaspiro[4.5]decan-8-yl)methyl]-2-chloroacetamide 在 lithium aluminium tetrahydride 、 四丁基溴化铵 作用下， 以 四氢呋喃 、 邻二氯苯 为溶剂， 反应 4.0h， 生成 Hexahydro-2H,6H-spiro[pyrido[1,2-a]pyrazine-7,2'-[1,3]dioxolane]
  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

• The Synthesis of 2,7-Substituted Octahydro-2H-Pyrido[1,2-a] Pyrazines, Analogues of Quinolizidine and Piperazine Drugs
  作者：M.Ashty Saleh、Frans Compernolle、Suzanne Toppet、Georges J. Hoornaert

  DOI：10.1016/s0040-4020(01)80853-x

  日期：1994.1

  versatility of amino ketone 2 (2-benzyloctahydro-2H-pyrido[1,2-a]pyrazin-7-one) was demonstrated by the synthesis of 2,7-substituted derivatives, designed as analogues of both quinolizidine and piperazine drugs. The 7- ketone group was functionalized via Grignard reaction with o- and p-fluorophenylmagnesium bromide, followed by dehydration and hydrogenation. Final substitution of the 2-amino group

  氨基酮2（2-苄基八氢-2H-吡啶并[1,2-a]吡嗪-7-酮）的多功能性通过合成2,7-取代的衍生物得到证明，该衍生物被设计为喹喔啉和哌嗪药物的类似物。通过与邻和对氟苯基溴化镁的格氏反应，将7-酮基官能化，然后进行脱水和氢化。2-氨基的最终取代得到2-吡啶基和对氟苯甲酰基目标化合物10和11。
• Saleh, M. Ashty; Compernolle, Frans; Toppet, Suzanne, Journal of the Chemical Society. Perkin transactions I, 1995, # 4, p. 369 - 372
  作者：Saleh, M. Ashty、Compernolle, Frans、Toppet, Suzanne、Hoornaert, Georges J.

  DOI：——

  日期：——
• Saleh M. Ashty, Compernolle Frans, Toppet Suzanne, Hoornaert Georges J., Tetrahedron, 50 (1994) N 6, S 1811-1820
  作者：Saleh M. Ashty, Compernolle Frans, Toppet Suzanne, Hoornaert Georges J.

  DOI：——

  日期：——