N-[(9-benzyl-1,4-dioxa-9-azaspiro[4.5]decan-8-yl)methyl]-2-chloro-N-phenylacetamide | 134334-45-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[(9-benzyl-1,4-dioxa-9-azaspiro[4.5]decan-8-yl)methyl]-2-chloro-N-phenylacetamide
• CAS: 134334-45-5
• 化学式: C₂₃H₂₇ClN₂O₃
• 分子量: 414.932
• InChiKey: LBWWSDIIXJQPBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  42.01
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-[(9-benzyl-1,4-dioxa-9-azaspiro[4.5]decan-8-yl)methyl]-2-chloro-N-phenylacetamide 在 四丁基溴化铵 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以74%的产率得到7-(Ethylenedioxy)-2-phenyloctahydro-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
• 作为产物：
  描述：

  1-Benzyl-5-(ethylenedioxy)-2-piperidinecarboxaldehyde 在 sodium cyanoborohydride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.92h， 生成 N-[(9-benzyl-1,4-dioxa-9-azaspiro[4.5]decan-8-yl)methyl]-2-chloro-N-phenylacetamide
  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