2-((1,3-dioxoisoindolin-2-yl)oxy)-2-methylpropanoic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-((1,3-dioxoisoindolin-2-yl)oxy)-2-methylpropanoic acid
• 英文别名: 2-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)oxy]-2-methylpropanoic acid；Propanoic acid, 2-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)oxy]-2-methyl-；2-(1,3-dioxoisoindol-2-yl)oxy-2-methylpropanoic acid
• 化学式: C₁₂H₁₁NO₅
• 分子量: 249.223
• InChiKey: FKFQTPMMDLGZPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-((1,3-dioxoisoindolin-2-yl)oxy)-2-methylpropanoic acid 在 O-苄基羟胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 N-(benzyloxy)-2-((1,3-dioxoisoindolin-2-yl)oxy)-2-methylpropanamide
  参考文献：
  名称：

  Pyridone-Conjugated Monobactam Antibiotics with Gram-Negative Activity

  摘要：

  Herein we describe the structure-aided design and synthesis of a series of pyridone-conjugated monohactam analogues with in vitro, antibacterial activity against clinically relevant Grain-negative species including Pseuedomonas aeruginosa, Klebsiella pneumoniae, and Escherichia coli. Rat pharmacokinetic studies with,compound 17 demonstrate low clearance and low plasma protein binding. In addition evidence is provided for a number of analogues suggesting that the siderophore receptors PiuA and PirA play a role in drug uptake in P. aeruginosa strain PAO1.

  DOI：

  10.1021/jm400560z
• 作为产物：
  描述：

  tert-butyl 2-(1,3-dioxoisoindolin-2-yloxy)-2-methylpropanoate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-((1,3-dioxoisoindolin-2-yl)oxy)-2-methylpropanoic acid
  参考文献：
  名称：

  酮衍生物和游离羧酸的远端 γ-C(sp3 )-H 烯化。

  摘要：

  本文报道了酮衍生物和游离羧酸的远端γ-C(sp 3 )-H烯化。微调先前报道的亚氨基酸导向基团并使用单N保护氨基酸（MPAA）和缺电子2-吡啶酮的配体组合对于γ-C(sp 3 )-H烯化至关重要酮底物。此外，MPAA 能够使游离羧酸发生 γ-C(sp 3 )-H 烯化反应，形成多种六元内酯。除了烷基羧酸之外，苄基 C(sp 3 )−H 键也可以通过 2-甲基苯甲酸衍生物一步功能化形成 3,4-二氢异香豆素结构。这些方案的实用性在大规模反应和 γ-C(sp 3 )−H 烯化产物的多样化中得到了证明。

  DOI：

  10.1002/anie.202003271

文献信息

• Photo-induced synthesis of β-sulfonyl imides from carboxylic acids
  作者：Linwei Zeng、Jian Jin、Jixiao He、Sunliang Cui

  DOI：10.1039/d1cc02559g

  日期：——

  A photo-induced imidation process of carboxylic acids is described. Numerous carboxylic acids could convert to β-sulfonyl imides in the presence of N-sulfonyl ynamides under visible light irradiation. Control experiments and mechanistic studies demonstrate that this imidation process involves a hydroacyloxylation/radical rearrangement cascade. This protocol represents a direct imidation method from

  描述了羧酸的光诱导酰亚胺化过程。在可见光照射下，在N-磺酰基炔酰胺的存在下，许多羧酸可以转化为 β-磺酰亚胺。对照实验和机理研究表明，这种酰亚胺化过程涉及氢酰氧基化/自由基重排级联。该协议代表了一种在温和条件下从羧酸直接酰亚胺化的方法，具有广泛的范围和高原子经济性。
• Metal-Free Cross-Dehydrogenative C–O Coupling of Carbonyl Compounds with <i>N</i>-Hydroxyimides: Unexpected Selective Behavior of Highly Reactive Free Radicals at an Elevated Temperature
  作者：Igor B. Krylov、Elena R. Lopat’eva、Alexander S. Budnikov、Gennady I. Nikishin、Alexander O. Terent’ev

  DOI：10.1021/acs.joc.9b02656

  日期：2020.2.21

  N-hydroxyphthalimide drastically affects the oxidative properties of t-BuOOt-Bu by intercepting the t-BuO• radicals with the formation of phthalimide-N-oxyl radicals, a species responsible for both hydrogen atom abstraction from the CH reagent and the selective formation of the C-O coupling product by selective radical cross-recombination. The practical applicability of the developed method was exemplified by the

  N-羟基酰亚胺与酮，酯和羧酸的交叉脱氢CO偶联是通过使用二叔丁基过氧化物作为自由基源和脱氢剂来实现的。所提出的方法在实验上很简单，并且证明了对于具有挑战性的CH底物（例如未活化的酯和羧酸）具有出色的效率。结果表明，N-羟基邻苯二甲酰亚胺通过拦截t-BuO•自由基而形成邻苯二甲酰亚胺-N-氧基自由基，从而极大地影响t-BuOOt-Bu的氧化性能。通过选择性自由基交叉重组选择性形成CO偶联产物。
• Monobactam hydrazides containing catechol sulfonic acid groups
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US05030724A1

  公开（公告）日：1991-07-09

  Antibacterial activity is exhibited by novel compounds having the formula ##STR1## or a pharmaceutically acceptable salt thereof. R.sub.3 and R.sub.4 are the same or different and each is hydrogen or alkyl or R.sub.3 and R.sub.4 taken together with the nitrogen atoms to which they are attached form a 1,2-diazacyclobutane, 1,2-diazacyclopentane, 1,2-diazacyclohexane, or 1,2-diazacycloheptane ring. Y.sub.1 and Y.sub.2 are either hydrogen or OR.sub.11 but are not the same. R.sub.11 is hydrogen, alkanoyl of from one to ten carbon atoms, substituted alkanoyl of from two to ten carbon atoms, phenylcarbonyl, (substituted phenyl) carbonyl, heteroarylcarbonyl, phenylalkanoyl, (substituted phenyl) alkanoyl, or heteroarylalkanoyl.

  新化合物具有以下结构式##STR1##或其药学上可接受的盐，表现出抗菌活性。R.sub.3和R.sub.4相同或不同，每个都是氢或烷基，或者R.sub.3和R.sub.4与它们连接的氮原子一起形成1,2-二氮杂环丁烷、1,2-二氮杂环戊烷、1,2-二氮杂环己烷或1,2-二氮杂环庚烷环。Y.sub.1和Y.sub.2可以是氢或OR.sub.11，但不能相同。R.sub.11是氢、由一至十个碳原子组成的烷酰基、由二至十个碳原子组成的取代烷酰基、苯甲酰基、(取代苯)甲酰基、杂环芳基甲酰基、苯基烷酰基、(取代苯)烷酰基或杂环芳基烷酰基。
• Photocatalytic Modular Cyanoalkylamination of Alkenes Involving Two Different Iminyl Radicals
  作者：Yu-Shi Jiang、Fu Liu、Miao-Sha Huang、Xue-Ling Luo、Peng-Ju Xia

  DOI：10.1021/acs.orglett.2c03233

  日期：2022.11.4

  The modular cyanoalkylamination of alkenes using bench-stable and easy-to-handle α-imino-oxy acid oxime esters as difunctional reagents creates new synthetic avenues. A metal-free photosensitization protocol for the installation of both amino and cyanoalkyl functionalities onto alkene feedstocks in a single step via two differently reactive nitrogen-centered radicals was developed via energy-transfer

  使用台式稳定且易于处理的 α-亚氨基-氧基酸肟酯作为双功能试剂的烯烃的模块化氰基烷基胺化创造了新的合成途径。通过能量转移催化开发了一种无金属光敏化方案，该方案通过两个不同的反应性氮中心自由基在一个步骤中将氨基和氰烷基官能团安装到烯烃原料上。优异的官能团耐受性和温和的反应条件也使该方案适用于药学相关分子衍生烯烃的氰基烷基胺化。
• Beta-Lactam compound, method for preparing the same, medicinal composition for bacterially infectious disease therapy containing the same and intermediates for synthesis of the same
  申请人：SANKEI PHARMACEUTICAL COMPANY LIMITED

  公开号：EP0254495A2

  公开（公告）日：1988-01-27

  There are disclosed a β-lactam compound represented by the formula (I): wherein R₁ and R₂ are independently a hydrogen atom or a lower alkyl group; M is a hydrogen atom, a protective group or an eliminatable group which is easily hydrolyzable in a human body; Rʹ and Rʺ are independently a hydrogen atom or a protective group; A is a mercapto group substituted by a sub­stituted or unsubstituted polycyclic nitrogen-con­taining heterocyclic ring or a group represented by the following formula (a):     -OOCNR₃R₄      (a) where R₃ and R₄ are independently a hydrogen atom or a lower alkyl group, provided that R₁ and R₂ are both hydrogen atoms, both R₃ and R₄ being hydrogen atoms are excluded, or its pharmaceutically acceptable salt, and a method for preparing the same, medicinal composition for microbism therapy containing the same and intermediates for synthesis of the same.

  本发明公开了一种β-内酰胺化合物，由式(I)表示： 其中 R₁ 和 R₂ 独立地为氢原子或低级烷基；M 为氢原子、保护基团或在人体内易水解的可消除基团；Rʹ 和 Rʺ 独立地为氢原子或保护基团；A 为被取代或未取代的多环含氮杂环取代的巯基或下式(a)所代表的基团： -OOCNR₃R₄ (a) 其中 R₃ 和 R₄ 独立地为氢原子或低级烷基、 但 R₁ 和 R₂ 均为氢原子，R₃ 和 R₄ 均为氢原子者除外、 或其药学上可接受的盐，以及制备上述物质的方法、含有上述物质的微生物治疗药物组合物和合成上述物质的中间体。