2-Azido-5-(4-phenyl-[1,2,3]triazol-1-yl)-hexanedioic acid dimethyl ester | 816452-59-2

• 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: 2-Azido-5-(4-phenyl-[1,2,3]triazol-1-yl)-hexanedioic acid dimethyl ester
• 英文别名: Dimethyl 2-azido-5-(4-phenyltriazol-1-yl)hexanedioate
• CAS: 816452-59-2
• 化学式: C₁₆H₁₈N₆O₄
• 分子量: 358.357
• InChiKey: BBVIENMPLTVWFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  97.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-Azido-5-(4-phenyl-[1,2,3]triazol-1-yl)-hexanedioic acid dimethyl ester 在 5percent Pd/C 盐酸 、 硼烷四氢呋喃络合物 、 氢气 、 methyloxirane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， -10.0~60.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 生成 5-(4-Phenyl-[1,2,3]triazol-1-yl)-piperidine-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of new triazole substituted pyroaminoadipic and pipecolic acid derivatives

  摘要：

  Racemic 5-(4,5-substituted-1H-1,2,3-triazol-lyl)-pyroaminoadipic and pipecolic acid derivatives were synthesized from meso dimethyl-alpha,alpha'-dibromoadipate 1 in good yields using mild reaction conditions. The key step of this reaction sequence was the 1,3-dipolar cycloaddition of an acetylenic compound on alpha-azido-alpha'-bromoadipate 2. A reactive alpha-(substituted-1H-1,2,3-triazol-1-yl)-alpha'- bromoadipate derivative 3a-d was generated and reacted with sodium azide followed by Pd/C-catalyzed hydrogenation to provide lactams 5a-d. The chemoselective reduction of the amide carbonyl group of 5a-d with BH3 followed by acid hydrolysis provided 5-(4,5-substituted-1H-1,2,3-triazol-1-yl) pipecolic acids in racemic form. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.09.166
• 作为产物：
  描述：

  dimethyl-α-azido-α'-bromoadipate 在 sodium azide 作用下， 以 丙酮 、 苯 为溶剂， 反应 24.0h， 生成 2-Azido-5-(4-phenyl-[1,2,3]triazol-1-yl)-hexanedioic acid dimethyl ester
  参考文献：
  名称：

  Synthesis of new triazole substituted pyroaminoadipic and pipecolic acid derivatives

  摘要：

  Racemic 5-(4,5-substituted-1H-1,2,3-triazol-lyl)-pyroaminoadipic and pipecolic acid derivatives were synthesized from meso dimethyl-alpha,alpha'-dibromoadipate 1 in good yields using mild reaction conditions. The key step of this reaction sequence was the 1,3-dipolar cycloaddition of an acetylenic compound on alpha-azido-alpha'-bromoadipate 2. A reactive alpha-(substituted-1H-1,2,3-triazol-1-yl)-alpha'- bromoadipate derivative 3a-d was generated and reacted with sodium azide followed by Pd/C-catalyzed hydrogenation to provide lactams 5a-d. The chemoselective reduction of the amide carbonyl group of 5a-d with BH3 followed by acid hydrolysis provided 5-(4,5-substituted-1H-1,2,3-triazol-1-yl) pipecolic acids in racemic form. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.09.166

文献信息

• Synthesis of new triazole substituted pyroaminoadipic and pipecolic acid derivatives
  作者：Fatimazohra Lenda、Farhate Guenoun、Bouchra Tazi、Najib Ben larbi、Jean Martinez、Frédéric Lamaty

  DOI：10.1016/j.tetlet.2004.09.166

  日期：2004.11

  Racemic 5-(4,5-substituted-1H-1,2,3-triazol-lyl)-pyroaminoadipic and pipecolic acid derivatives were synthesized from meso dimethyl-alpha,alpha'-dibromoadipate 1 in good yields using mild reaction conditions. The key step of this reaction sequence was the 1,3-dipolar cycloaddition of an acetylenic compound on alpha-azido-alpha'-bromoadipate 2. A reactive alpha-(substituted-1H-1,2,3-triazol-1-yl)-alpha'- bromoadipate derivative 3a-d was generated and reacted with sodium azide followed by Pd/C-catalyzed hydrogenation to provide lactams 5a-d. The chemoselective reduction of the amide carbonyl group of 5a-d with BH3 followed by acid hydrolysis provided 5-(4,5-substituted-1H-1,2,3-triazol-1-yl) pipecolic acids in racemic form. (C) 2004 Elsevier Ltd. All rights reserved.