4-(羟甲基)-2-氮杂环丁酮 | 74694-48-7

• 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-(羟甲基)-2-氮杂环丁酮
• 中文别名: 4-(羟甲基)氮杂环丁烷-2-酮
• 英文名称: 4-(hydroxymethyl)azetidin-2-one
• 英文别名: 4(S)-4-hydroxymethyl azetidin-2-one
• CAS: 74694-48-7
• 化学式: C₄H₇NO₂
• mdl: MFCD19217317
• 分子量: 101.105
• InChiKey: YTUSUDPOSFRAEO-UHFFFAOYSA-N

物化性质

• 熔点：
  60-66℃
• 沸点：
  355.8±15.0 °C(Predicted)
• 密度：
  1.231±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933790090

反应信息

• 作为反应物：
  描述：

  4-(羟甲基)-2-氮杂环丁酮 、 2-氟吡啶 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 以16.5%的产率得到4-((pyridin-2-yloxy)methyl)azetidin-2-one
  参考文献：
  名称：

  [EN] COMPOUNDS TARGETING RNA-BINDING PROTEINS OR RNA-MODIFYING PROTEINS
  [FR] COMPOSÉS CIBLANT DES PROTÉINES DE LIAISON À L'ARN OU DES PROTÉINES MODIFIANT L'ARN

  摘要：

  该发明涉及由化学式（I）表示的化合物，或其药用可接受盐，包括含有该化合物的组合物以及制备和使用该化合物的方法。这里描述了变量。

  公开号：

  WO2021178420A1
• 作为产物：
  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

文献信息

• β-Lactams. XI. Synthesis of <i>N</i>-phosphorylated mono- and bicyclic β-lactams
  作者：George Just、Denise Dugat、Whi-Yu Liu

  DOI：10.1139/v83-296

  日期：1983.8.1

  Starting from appropriately.substituted monocyclic β-lactam, N-phosphorylated mono- and bicyclic β-lactams have been synthesized.

  从适当替代的单环β-内酰胺出发，已合成了N-磷酸化的单环和双环β-内酰胺。
• Tethered Aminohydroxylation (TA) Reaction of Amides
  作者：Timothy J. Donohoe、Cedric K. A. Callens、Amber L. Thompson

  DOI：10.1021/ol900631y

  日期：2009.6.4

  The first examples of amide-tethered aminohydroxylation reactions, catalyzed by osmium, showing that the use of N−O-based reoxidants are essential for success, are reported. The system that is described is compatible with a variety of different alkene substitution patterns and ring sizes and works with low loadings in both cyclic and acyclic systems. The levels of diastereoselectivity that were observed

  据报道，催化的酰胺束缚的氨基羟基化反应的第一个例子表明，使用基于N-O的再氧化剂对成功至关重要。所描述的系统与多种不同的烯烃取代方式和环大小兼容，并且在环状和非环状系统中均以低负荷运行。对于在有机合成中使用立体选择性TA反应而言，对于在烯丙基和烯丙基位置上的取代基都观察到的非对映选择性水平很好。
• Brennan, John; Richardson, Geoffrey; Stoodley, Richard J., Journal of the Chemical Society. Chemical communications, 1980, # 2, p. 49
  作者：Brennan, John、Richardson, Geoffrey、Stoodley, Richard J.

  DOI：——

  日期：——
• Brennan, John; Richardson, Geoffrey; Stoodley, Richard J., Journal of the Chemical Society. Perkin transactions I, 1983, p. 649 - 655
  作者：Brennan, John、Richardson, Geoffrey、Stoodley, Richard J.

  DOI：——

  日期：——
• BRENNAN J.; RICHARDSON G.; STOODLEY R. J., J. CHEM. SOC. CHEM. COMMUN., 1980, NO 2, 49
  作者：BRENNAN J.、 RICHARDSON G.、 STOODLEY R. J.

  DOI：——

  日期：——