4-(benzyloxyamino)-4-oxobutanoic acid | 56439-34-0

• 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: 4-(benzyloxyamino)-4-oxobutanoic acid
• 英文别名: N-benzyloxy-succinamic acid；N-Benzyloxy-succinamidsaeure；4-oxo-4-[(phenylmethoxy)amino]butanoic acid；3-benzyloxycarbamoyl-propionic acid；Butanoic acid, 4-benzyloxyamino-4-oxo-；4-oxo-4-(phenylmethoxyamino)butanoic acid
• CAS: 56439-34-0
• 化学式: C₁₁H₁₃NO₄
• 分子量: 223.229
• InChiKey: JPAYUEFYDOGISN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(benzyloxyamino)-4-oxobutanoic acid 在 3 A molecular sieve 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 24.0h， 生成 2-(1-benzylcarbamoyl-3-methylbutylamino)ethyl 3-benzyloxycarbamoylpropanoate
  参考文献：
  名称：

  Ugi Multicomponent Reaction Followed by an Intramolecular Nucleophilic Substitution:  Convergent Multicomponent Synthesis of 1-Sulfonyl 1,4-Diazepan-5-ones and of Their Benzo-Fused Derivatives

  摘要：

  A short, two-step approach to the synthesis of diazepane or diazocane systems, based on a Ugi multicomponent reaction followed by a subsequent intramolecular S(N)2 reaction was studied. 1-Sulfonyl tetrahydrobenzo[e]-1,4-diazepin-1-ones 1 were obtained in very high yield through a Ugi multicomponent reaction followed by Mitsunobu cyclization. On the other hand, aliphatic 1-sulfonyl 1,4-diazepan-5-ones 2 could be obtained employing different cyclization conditions (sulfuryl diimidazole). A similar approach toward diazocane rings using hydroxamates as nucleophiles was less successful, affording only O-cyclized adducts or unexpected side products. A mechanistic explanation of the observed outcomes is proposed.

  DOI：

  10.1021/jo062626z
• 作为产物：
  描述：

  丁二酸酐 、 苄氧基胺盐酸盐 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 sodium hydroxide 为溶剂， 生成 4-(benzyloxyamino)-4-oxobutanoic acid
  参考文献：
  名称：

  Carboxy and substituted carboxy alkanoyl and cycloalkanoyl peptides

  摘要：

  公式为##STR1##的肽，在其中X是各种氨基或亚氨基酸或酯，可用作降压剂。

  公开号：

  US04499079A1

文献信息

• Studies concerning the antibiotic actinonin. Part IV. Synthesis of structural analogues of actinonin by the mixed anhydride method
  作者：Barbara J. Broughton、Peter J. Warren、Kenneth R. H. Wooldridge、Derek E. Wright、W. David Ollis、Ronald J. Wood

  DOI：10.1039/p19750000842

  日期：——

  The reaction between alkylsuccinic anhydrides (III) and O-benzylhydroxylamine yields the acids (VI). These acids (VI) may be coupled with amino-amides (II) by the mixed anhydride procedure, giving a mixture of the racemates (VIII) and (IX). Hydrogenolysis of the O-benzylhydroxamic acids (VIII) and (IX) yields structural analogues [(X) and (XI)] of the natural antibiotic actinonin (I).

  烷基琥珀酸酐（III）和O-苄基羟胺之间的反应产生酸（VI）。这些酸（VI）可以通过混合酸酐法与氨基酰胺（II）偶联，得到外消旋物（VIII）和（IX）的混合物。O-苄基异羟肟酸（VIII）和（IX）的氢解产生天然抗生素肌动蛋白（I）的结构类似物[（X）和（XI）] 。
• Inhibitors of the FEZ-1 metallo-β-lactamase
  作者：Benoît M.R. Liénard、Louise E. Horsfall、Moreno Galleni、Jean-Marie Frère、Christopher J. Schofield

  DOI：10.1016/j.bmcl.2006.11.053

  日期：2007.2

  Metallo-beta-lactamases (MBLs) catalyze the hydrolysis of beta-lactams including penicillins, cephalosporins and carbapenems. Starting from benzohydroxamic acid (1) structure-activity studies led to the identification of selective inhibitors of the FEZ-1 MBL, e.g., 2,5-substituted benzophenone hydroxamic acid 17 has a K-i of 6.1 +/- 0.71 mu M against the FEZ-1 MBL but does not significantly inhibit the IMP-1, Bell, CphA or L1 MBLs. (c) 2006 Elsevier Ltd. All rights reserved.
• The synthesis of some N-hydroxyimides
  作者：D. E. Ames、T. F. Grey

  DOI：10.1039/jr9550000631

  日期：——
• 2-Oxoglutarate analogue inhibitors of prolyl hydroxylase domain 2
  作者：Jasmin Mecinović、Christoph Loenarz、Rasheduzzaman Chowdhury、Christopher J. Schofield

  DOI：10.1016/j.bmcl.2009.09.005

  日期：2009.11

  Analogues of the 2-oxoglutarate cosubstrate of the human oxygen sensing enzyme prolyl hydroxylase domain 2 (PHD2) with variations in the potential iron-chelating group were screened as inhibitors and for binding (using non-denaturing electrospray ionization mass spectrometry) to PHD2. (c) 2009 Elsevier Ltd. All rights reserved.
• US4499079A
  申请人：——

  公开号：US4499079A

  公开（公告）日：1985-02-12