N-(苯基甲氧基)-1,5-戊二胺 | 160388-21-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(苯基甲氧基)-1,5-戊二胺
• 中文别名: N1-(苯基甲氧基)-1,5-戊烷二胺；甲磺酸去铁敏中间体3
• 英文名称: N-(Benzyloxy)-1,5-pentanediamine
• 英文别名: N-(Phenylmethoxy)-1,5-pentanediamine；N'-phenylmethoxypentane-1,5-diamine
• CAS: 160388-21-6
• 化学式: C₁₂H₂₀N₂O
• 分子量: 208.304
• InChiKey: WLGYQCPSHWDABN-UHFFFAOYSA-N

物化性质

• 沸点：
  324.0±52.0 °C(Predicted)
• 密度：
  1.005
• 溶解度：
  溶于二氯甲烷、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  47.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(苯基甲氧基)-1,5-戊二胺 在 palladium on activated charcoal 吡啶 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 25.0~81.0 ℃ 、101.33 kPa 条件下， 反应 63.33h， 生成 1-(tert-Butoxycarbonyl)-7,18,29-trihydroxy-8,11,19,22,30-pentaoxo-1,7,12,18,23,29-hexaazahentriacontane
  参考文献：
  名称：

  A Versatile Synthesis of Deferrioxamine B

  摘要：

  A new and versatile route to N'-[5-[[4-[[5-(acetylhydroxyamino)pentyl]amino]-1,4-dioxobutyl]-hydroxyamino]pentyl]-N-(5-aminopentyl)-N-hydroxybutanediamide, deferrioxamine B (DFO), is described. The key improvement over the two prior routes was replacement of the nitrile in 2 with a tert-butoxycarbonyl-protected amino terminus. Elimination of the nitrile improved the kinetics of hydrogenation in that the benzyl groups of 12 were cleaved more rapidly than saturation of the cyano group of 2, and a potential overreduction byproduct (4) was thus avoided. N-(Benzyloxy)-1,5-diaminopentane (6) was selectively protected at the primary amino site with a tert-butoxycarbonyl (BOG) group, providing 7. This was reacted at the (benzyloxy)amine with succinic anhydride to produce carboxylic acid 8, which was in turn acylated regiospecifically with diamine 6 at the primary amine to give (benzyloxy)amine 9. The previous two steps were reiterated to afford DFO reagent 11. This synthon allows for modification of DFO at either end of the molecule, thus providing more flexibility in accessing DFO analogues than any prior route. Acetylation of TI, followed by hydrogenolysis and tert-butoxycarbonyl group removal, furnished DFO.

  DOI：

  10.1021/jo00106a022
• 作为产物：
  描述：

  N-(5-溴戊基)邻苯二甲酰亚胺 在 一水合肼 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 7.5h， 生成 N-(苯基甲氧基)-1,5-戊二胺
  参考文献：
  名称：

  Kolasa, Teodozyj; Chimiak, Andrzej, Polish Journal of Chemistry, 1981, vol. 55, # 5, p. 1163 - 1167

  摘要：

  DOI：

文献信息

• METHOD FOR PREPARING DESFERRIOXAMINE B AND HOMOLOGS THEREOF
  申请人：UNIVERSITY OF FLORIDA RESEARCH FOUNDATION, INC.

  公开号：EP0799192A1

  公开（公告）日：1997-10-08
• US5493053A
  申请人：——

  公开号：US5493053A

  公开（公告）日：1996-02-20
• [EN] METHOD FOR PREPARING DESFERRIOXAMINE B AND HOMOLOGS THEREOF<br/>[FR] PROCEDE DE PREPARATION DE LA DESFERRIOXAMINE B ET DE SES HOMOLOGUES
  申请人：UNIVERSITY OF FLORIDA RESEARCH FOUNDATION, INC.

  公开号：WO1996019441A1

  公开（公告）日：1996-06-27

  (EN) A new and versatile route to N'-[5-[[4-[[5-(acetylhydroxyamino)pentyl]amino]-1,4-dioxobutyl]hydroxyamino]pentyl]-N-(5-aminopentyl)-N-hydroxybutanediamide, desferrioxamine B (DFO) is described. N-Benzyloxy-1,5-diaminopentane is selectively protected at the primary amino site. The product is reacted at the benzyloxyamine with an anhydride to produce a carboxylic acid which is, in turn, acylated regiospecifically with a diamine at the primary amine to give a benzyloxyamine. The previous two steps are repeated to afford a DFO reagent. Acetylation of the DFO reagent, followed by hydrogenolysis and tert-butoxycarbonyl group removal, furnishes DFO.(FR) L'invention décrit une méthode nouvelle et à applications multiples pour obtenir N'-[5-[[4-[[5-(acétylhydroxyamino)pentyl]amino]-1, 4-dioxobutyl]hydroxyamino]pentyl]-N-(5-aminopentyl)-N-hydroxybutanediamide, desferrioxamine B (DFO). N-benzyloxy-1,5-diaminopentane est inhibé sélectivement sur le site amino primaire. Le produit est mis à réagir sur la benzyloxyamine avec un anhydride pour obtenir un acide carboxylique qui est à son tour acylé dans une région spécifique avec une diamine sur l'amine primaire pour donner une benzyloxyamine. Les deux étapes précédentes sont répétées pour obtenir un réactif DFO. L'acétylation dudit réactif, suivie d'une hydrogénolyse et du retrait du groupe tert-butoxycarbonyle, donne de la DFO.
• Kolasa, Teodozyj; Chimiak, Andrzej, Polish Journal of Chemistry, 1981, vol. 55, # 5, p. 1163 - 1167
  作者：Kolasa, Teodozyj、Chimiak, Andrzej

  DOI：——

  日期：——
• A Versatile Synthesis of Deferrioxamine B
  作者：Raymond J. Bergeron、James S. McManis、Otto IV Phanstiel、J. R. Timothy Vinson

  DOI：10.1021/jo00106a022

  日期：1995.1

  A new and versatile route to N'-[5-[[4-[[5-(acetylhydroxyamino)pentyl]amino]-1,4-dioxobutyl]-hydroxyamino]pentyl]-N-(5-aminopentyl)-N-hydroxybutanediamide, deferrioxamine B (DFO), is described. The key improvement over the two prior routes was replacement of the nitrile in 2 with a tert-butoxycarbonyl-protected amino terminus. Elimination of the nitrile improved the kinetics of hydrogenation in that the benzyl groups of 12 were cleaved more rapidly than saturation of the cyano group of 2, and a potential overreduction byproduct (4) was thus avoided. N-(Benzyloxy)-1,5-diaminopentane (6) was selectively protected at the primary amino site with a tert-butoxycarbonyl (BOG) group, providing 7. This was reacted at the (benzyloxy)amine with succinic anhydride to produce carboxylic acid 8, which was in turn acylated regiospecifically with diamine 6 at the primary amine to give (benzyloxy)amine 9. The previous two steps were reiterated to afford DFO reagent 11. This synthon allows for modification of DFO at either end of the molecule, thus providing more flexibility in accessing DFO analogues than any prior route. Acetylation of TI, followed by hydrogenolysis and tert-butoxycarbonyl group removal, furnished DFO.