4-氧代-2-氮杂啶羧酸苯甲酯 | 87791-58-0

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 中文名称: 4-氧代-2-氮杂啶羧酸苯甲酯
• 中文别名: 苄基4-氧代氮杂环丁烷-2-甲酸酯
• 英文名称: 4-(benzyloxycarbonyl)-2-azetidinone
• 英文别名: azetidinone-4-carboxylic acid benzyl ester；Benzyl 4-oxoazetidine-2-carboxylate
• CAS: 87791-58-0
• 化学式: C₁₁H₁₁NO₃
• mdl: MFCD00661973
• 分子量: 205.213
• InChiKey: WGLLBHSIXLWVFU-UHFFFAOYSA-N

物化性质

• 沸点：
  404.7±38.0 °C(Predicted)
• 密度：
  1.268±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933790090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  4-氧代-2-氮杂啶羧酸苯甲酯 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以92%的产率得到4-(羟甲基)-2-氮杂环丁酮
  参考文献：
  名称：

  Ternary Nylon-3 Copolymers as Host-Defense Peptide Mimics: Beyond Hydrophobic and Cationic Subunits

  摘要：

  Host-defense peptides (HDPs) are produced by eukaryotes to defend against bacterial infection, and diverse synthetic polymers have recently been explored as mimics of these natural peptides. HDPs are rich in both hydrophobic and cationic amino acid residues, and most HDP-mimetic polymers have therefore contained binary combinations of hydrophobic and cationic subunits. However, HDP-mimetic polymers rarely duplicate the hydrophobic surface and cationic charge density found among HDPs (Hu , K.; et al. Macromolecules 2013 , 46 , 1908); the charge and hydrophobicity are generally higher among the polymers. Statistical analysis of HDP sequences (Wang , G.; et al. Nucleic Acids Res. 2009 , 37 , D933) has revealed that serine (polar but uncharged) is a very common HDP constituent and that glycine is more prevalent among HDPs than among proteins in general. These observations prompted us to prepare and evaluate ternary nylon-3 copolymers that contain a modestly polar but uncharged subunit, either serine-like or glycine-like, along with a hydrophobic subunit and a cationic subunit. Starting from binary hydrophobic-cationic copolymers that were previously shown to be highly active against bacteria but also highly hemolytic, we found that replacing a small proportion of the hydrophobic subunit with either of the polar, uncharged subunits can diminish the hemolytic activity with minimal impact on the antibacterial activity. These results indicate that the incorporation of polar, uncharged subunits may be generally useful for optimizing the biological activity profiles of antimicrobial polymers. In the context of HDP evolution, our findings suggest that there is a selective advantage to retaining polar, uncharged residues in natural antimicrobial peptides.

  DOI：

  10.1021/ja507576a
• 作为产物：
  描述：

  二苄基2-氨基琥珀酸酯 在 三甲基氯硅烷 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以67%的产率得到4-氧代-2-氮杂啶羧酸苯甲酯
  参考文献：
  名称：

  Ternary Nylon-3 Copolymers as Host-Defense Peptide Mimics: Beyond Hydrophobic and Cationic Subunits

  摘要：

  Host-defense peptides (HDPs) are produced by eukaryotes to defend against bacterial infection, and diverse synthetic polymers have recently been explored as mimics of these natural peptides. HDPs are rich in both hydrophobic and cationic amino acid residues, and most HDP-mimetic polymers have therefore contained binary combinations of hydrophobic and cationic subunits. However, HDP-mimetic polymers rarely duplicate the hydrophobic surface and cationic charge density found among HDPs (Hu , K.; et al. Macromolecules 2013 , 46 , 1908); the charge and hydrophobicity are generally higher among the polymers. Statistical analysis of HDP sequences (Wang , G.; et al. Nucleic Acids Res. 2009 , 37 , D933) has revealed that serine (polar but uncharged) is a very common HDP constituent and that glycine is more prevalent among HDPs than among proteins in general. These observations prompted us to prepare and evaluate ternary nylon-3 copolymers that contain a modestly polar but uncharged subunit, either serine-like or glycine-like, along with a hydrophobic subunit and a cationic subunit. Starting from binary hydrophobic-cationic copolymers that were previously shown to be highly active against bacteria but also highly hemolytic, we found that replacing a small proportion of the hydrophobic subunit with either of the polar, uncharged subunits can diminish the hemolytic activity with minimal impact on the antibacterial activity. These results indicate that the incorporation of polar, uncharged subunits may be generally useful for optimizing the biological activity profiles of antimicrobial polymers. In the context of HDP evolution, our findings suggest that there is a selective advantage to retaining polar, uncharged residues in natural antimicrobial peptides.

  DOI：

  10.1021/ja507576a

文献信息

• Antibiotic synthesis
  申请人：——

  公开号：US05998612A1

  公开（公告）日：1999-12-07

  A method of preparing intermediates for carbapenem antibiotics characterized by treating a N-deprotected acetoxy conpound of the formula: ##STR1## in the presence of a Lewis acid or a silylating agent to yeild an intermediate; and cyclizing the intermediate in the presence of rhodium (II) acetate to form a bicyclic ketoester.

  一种制备碳青霉烯类抗生素中间体的方法，其特征在于将式子为##STR1##的N-去保护的乙酰氧基化合物在Lewis酸或硅化剂存在下处理，得到一个中间体；并在存在二价铑醋酸盐的情况下使中间体环化，形成一个双环酮酯。
• Practical and efficient synthesis of N-halo compounds
  作者：Yong-Li Zhong、Hua Zhou、Donald R. Gauthier、Jaemoon Lee、David Askin、Ulf H. Dolling、Ralph P. Volante

  DOI：10.1016/j.tetlet.2004.12.088

  日期：2005.2

  A practical and efficient synthesis of N-halo compounds is described. Treatment of primary and secondary amines or amides with sodium hypohalite in the presence of tert-butanol and acetic acid afforded N-halo compounds in 90–100% yield.

  描述了一种实用且有效的N-卤代化合物的合成。在叔丁醇和乙酸存在下，用次卤酸钠处理伯胺和仲胺或酰胺，可制得90-100％的N-卤代化合物。
• Substituted azetidinones as anti-inflammatory and antidegenerative agents
  申请人：Merck & Co., Inc.

  公开号：US05229381A1

  公开（公告）日：1993-07-20

  New substituted azetidinones of the general formula (A') which have been found to be potent elastase inhibitors and thereby useful anti-inflammatory and antidegenerative agents are described. ##STR1##

  已发现具有强大弹性蛋白酶抑制剂作用的通用公式（A'）的新替代氮杂环丙酮类化合物，并因此被用作有用的抗炎和抗退行性药物。
• Protecting group migration in the chemistry of 1-t-butyldimethylsilyl-4-hydroxymethyl-2-azetidinone
  作者：Stéphane Gérard、Jacqueline Marchand-Brynaert

  DOI：10.1016/s0040-4039(03)01525-9

  日期：2003.8

  The alkoxide anion derived from 1-t-butyldimethylsilyl-4-hydroxymethyl-2-azetidinone (1) rearranged at −78°C into amide anion by N–O migration of the silyl protecting group. The occurrence of this intermediate was proved by quenching with benzyl bromide and phenethyl chloroformate, giving respectively N-benzyl (4) and N-(phenethyloxycarbonyl) (6) derivatives of 4-(t-butyldimethylsilyloxy)methyl-2-azetidinone

  由1-叔丁基二甲基甲硅烷基-4-羟甲基-2-氮杂环丁酮（1）衍生的醇盐阴离子在甲硅烷基保护基团的N–O迁移下于-78°C重排为酰胺阴离子。通过用苄基溴和氯甲酸苯乙酯淬灭证明该中间体的存在，分别得到4-（叔丁基二甲基甲硅烷氧基）甲基-2-氮杂环丁酮的N-苄基（4）和N-（苯乙氧基羰基）（6）衍生物。
• Synthesis, hydrolysis, biochemical and theoretical evaluation of 1,4-bis(alkoxycarbonyl)azetidin-2-ones as potential elastase inhibitors
  作者：Stéphane Gérard、Georges Dive、Brigitte Clamot、Roland Touillaux、Jacqueline Marchand-Brynaert

  DOI：10.1016/s0040-4020(02)00112-6

  日期：2002.3

  A series of 1,4-bis(alkoxycarbonyl)azetidin-2-ones, designed as potential suicide-inhibitors of serine proteases, has been synthesized and evaluated against porcine pancreatic elastase (PPE). The most active compound (Ki∼10 μM; reversible inhibitor) was equipped with phenethyloxycarbonyl and benzyloxycarbonyl side-chains at positions N1 and C4, respectively, with the (S)-configuration. 1H NMR spectroscopic

  合成了一系列设计为丝氨酸蛋白酶的潜在自杀抑制剂的1,4-双（烷氧基羰基）氮杂环丁烷-2-酮，并针对猪胰弹性蛋白酶（PPE）进行了评估。最活跃的化合物（ķ我〜10μM;可逆抑制剂）装备有分别在位置N1和C4，苯乙苄氧基羰基和侧链，与（小号） -构型。1个反应混合物的1 H NMR光谱分析表明，就氮杂环丁酮和氨基甲酸酯的功能而言，在化学和酶催化的反应中，酯的功能均优先被水解。考虑到三个潜在敏感的羰基官能团和两个立体异构体，从头算来确定在酶口袋模型中达到水解的过渡态结构所需的能垒。