N-<5-(tert-Butyloxycarbonyl)pentyl>-4,5-bisamino>valeramide | 158141-63-0

• 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: N-<5-(tert-Butyloxycarbonyl)pentyl>-4,5-bisamino>valeramide
• 英文别名: N-[5-(tert-butyloxycarbonyl)pentyl]-4,5-bis[(bis(benzyloxycaxbonyl)methyl)amino]valeramide；Tert-butyl 6-[4,5-bis[bis(2-oxo-2-phenylmethoxyethyl)amino]pentanoylamino]hexanoate
• CAS: 158141-63-0
• 化学式: C₅₁H₆₃N₃O₁₁
• 分子量: 894.075
• InChiKey: PCYYZYDMZWUZOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  65
• 可旋转键数：
  34
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  167
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  N-<5-(tert-Butyloxycarbonyl)pentyl>-4,5-bisamino>valeramide 在 三氟乙酸 作用下， 反应 2.0h， 以93%的产率得到N-(5-Carboxypentyl)-4,5-bisamino>valeramide
  参考文献：
  名称：

  A Conceptual Approach to the Synthesis of Bifunctional EDTA Analogs: EDTA-Extended Polyamides

  摘要：

  A conceptual approach to the synthesis of epsilon-carboxyl and epsilon-amino polyamide-linked EDTAs is proposed (Scheme 1), starting from epsilon-carboxy vicinal diamine blocked by Cbz or Boc groups (A, Scheme 1), followed by extension along the chain to form polyamides with epsilon-carboxy groups (A(2),A(3),..., A(n)) or amine groups (B-1, B-2,..., B-n). The A(n) series can be converted to acidic EDTAs (AE(n) series) or basic EDTAs (BE(n) series). This depends on the selection of the protecting groups to offer exclusive protection of the amine and acid functions. The choice of the protecting groups (three categories a-c in Scheme 1) provides an exclusive synthetic methodology. This is further exploited for conversion of acidic polyamide-linked EDTA (AE(n)) to either acidic or basic EDTA homologs (see Scheme 2). Scheme 4 proposes methodology for synthesis of terminally blocked bis-EDTA polyamides.

  DOI：

  10.1021/jo00096a025
• 作为产物：
  描述：

  6-氨基己酸 在 palladium on activated charcoal sodium hydroxide 、 硫酸 、 氢气 、 1,8-双二甲氨基萘 、 三乙胺 、 sodium iodide 作用下， 以 乙醇 、 二氯甲烷 、 氯仿 、 乙腈 为溶剂， 25.0~84.0 ℃ 、199.98 Pa 条件下， 反应 159.5h， 生成 N-<5-(tert-Butyloxycarbonyl)pentyl>-4,5-bisamino>valeramide
  参考文献：
  名称：

  A Conceptual Approach to the Synthesis of Bifunctional EDTA Analogs: EDTA-Extended Polyamides

  摘要：

  A conceptual approach to the synthesis of epsilon-carboxyl and epsilon-amino polyamide-linked EDTAs is proposed (Scheme 1), starting from epsilon-carboxy vicinal diamine blocked by Cbz or Boc groups (A, Scheme 1), followed by extension along the chain to form polyamides with epsilon-carboxy groups (A(2),A(3),..., A(n)) or amine groups (B-1, B-2,..., B-n). The A(n) series can be converted to acidic EDTAs (AE(n) series) or basic EDTAs (BE(n) series). This depends on the selection of the protecting groups to offer exclusive protection of the amine and acid functions. The choice of the protecting groups (three categories a-c in Scheme 1) provides an exclusive synthetic methodology. This is further exploited for conversion of acidic polyamide-linked EDTA (AE(n)) to either acidic or basic EDTA homologs (see Scheme 2). Scheme 4 proposes methodology for synthesis of terminally blocked bis-EDTA polyamides.

  DOI：

  10.1021/jo00096a025

文献信息

• Pharmaceutical compositions comprising iron chelators for the treatment of neurodegenerative disorders and some novel iron chelators
  申请人：Warshawsky Rivka

  公开号：US06855711B1

  公开（公告）日：2005-02-15

  Use of a compound of formula (I), wherein R 1 is H or hydrocarbyl; R 2 is a hydrophobic radical; R 3 is 3-(C 2 -C 6 )acyl-4-hydroxyphenyl, 3-hydroxyimino (C 2 -C 6 )-alkyl-4-hydroxyphenyl, or COOZ, wherein Z is H, (C 1 -C 6 ) alkyl, aryl, aryl or ar(C 1 -C 6 ) alkyl; and n is 1-20; and of a compound of formula (II), wherein R 4 is (C 1 -C 6 ) alkyl, cyano (C 1 -C 6 ) alkyl, (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl or —CH 2 NR 7 R 8 , wherein R 7 and R 8 , the same or different, is each H or (C 1 -C 6 ) alkyl, or together with the N atom form a saturated or unsaturated 5-7 membered ring optionally containing a further heteroatom selected from N, O or S, the further N atom being optionally substituted, and either R 5 is H and R 6 is (C 2 -C 6 ) acyl or hydroxyimino (C 2 -C 6 ) alkyl, or R 5 and R 6 together with the phenyl ring form a quinoline, a 1,2,3,4-tetrahydroquinoline or a perhydroquinoline ring, for the preparation of pharmaceutical compositions for the treatment of Parkinson's disease or stroke.

  使用式(I)的化合物，其中R1是H或烃基；R2是疏水基团；R3是3-(C2-C6)酰基-4-羟基苯基，3-羟基亚氨基(C2-C6)-烷基-4-羟基苯基，或COOZ，其中Z是H，(C1-C6)烷基，芳基，芳基或芳基(C1-C6)烷基；n为1-20；以及使用式(II)的化合物，其中R4是(C1-C6)烷基，氰基(C1-C6)烷基，(C1-C6)氧基(C1-C6)烷基或—CH2NR7R8，其中R7和R8，相同或不同，各为H或(C1-C6)烷基，或与N原子一起形成一个饱和或不饱和的5-7元环，可选择地含有进一步选择自N、O或S的杂原子，进一步的N原子可选择地被取代，且R5为H且R6为(C2-C6)酰基或羟亚氨基(C2-C6)烷基，或R5和R6与苯环一起形成喹啉、1,2,3,4-四氢喹啉或全氢喹啉环，用于制备治疗帕金森病或中风的药物组合物。
• A Conceptual Approach to the Synthesis of Bifunctional EDTA Analogs: EDTA-Extended Polyamides
  作者：N. Kahana、R. Arad-Yellin、A. Warshawsky

  DOI：10.1021/jo00096a025

  日期：1994.8

  A conceptual approach to the synthesis of epsilon-carboxyl and epsilon-amino polyamide-linked EDTAs is proposed (Scheme 1), starting from epsilon-carboxy vicinal diamine blocked by Cbz or Boc groups (A, Scheme 1), followed by extension along the chain to form polyamides with epsilon-carboxy groups (A(2),A(3),..., A(n)) or amine groups (B-1, B-2,..., B-n). The A(n) series can be converted to acidic EDTAs (AE(n) series) or basic EDTAs (BE(n) series). This depends on the selection of the protecting groups to offer exclusive protection of the amine and acid functions. The choice of the protecting groups (three categories a-c in Scheme 1) provides an exclusive synthetic methodology. This is further exploited for conversion of acidic polyamide-linked EDTA (AE(n)) to either acidic or basic EDTA homologs (see Scheme 2). Scheme 4 proposes methodology for synthesis of terminally blocked bis-EDTA polyamides.