2,2-Dimethyl-5-pentyl-1,3-dioxane-4,6-dione | 1401900-72-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-Dimethyl-5-pentyl-1,3-dioxane-4,6-dione
• CAS: 1401900-72-8
• 化学式: C₁₁H₁₈O₄
• 分子量: 214.262
• InChiKey: MTOCUXHEVRHESJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2-Dimethyl-5-pentyl-1,3-dioxane-4,6-dione 、 tetra-acetyl glucosamine 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以37%的产率得到(2S,3R,4S,5S,6R)-6-(acetoxymethyl)-3-(3-oxooctanamido)tetrahydro-2H-pyran-2,4,5-triyl triacetate
  参考文献：
  名称：

  Synthesis of antimicrobial glucosamides as bacterial quorum sensing mechanism inhibitors

  摘要：

  Bacteria communicate with one another and regulate their pathogenicity through a phenomenon known as quorum sensing (QS). When the bacterial colony reaches a threshold density, the QS system induces the production of virulence factors and the formation of biofilms, a powerful defence system against the host's immune responses. The glucosamine monomer has been shown to disrupt the bacterial QS system by inhibiting autoinducer (AI) signalling molecules such as the acyl-homoserine lactones (AHLs). In this study, the synthesis of acetoxy-glucosamides 8, hydroxy-glucosamides 9 and 3-oxo-glucosamides 12 was performed via the 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC center dot HCl) and N, N'-dicyclohexylcarbodiimide (DCC) coupling methods. All of the synthesized compounds were tested against two bacterial strains, P. aeruginosa MH602 (LasI/R-type QS) and E. coli MT102 (LuxI/R-type QS), for QS inhibitory activity. The most active compound 9b showed 79.1% QS inhibition against P. aeruginosa MH602 and 98.4% against E. coli MT102, while compound 12b showed 64.5% inhibition against P. aeruginosa MH602 and 88.1% against E. coli MT102 strain at 2 mM concentration. The ability of the compounds to inhibit the production of the virulence factor pyocyanin and biofilm formation in the P. aeruginosa (PA14) strain was also examined. Finally, computational docking studies were performed with the LasR receptor protein. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.12.024
• 作为产物：
  描述：

  丙二酸环(亚)异丙酯 、 己酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 2,2-Dimethyl-5-pentyl-1,3-dioxane-4,6-dione
  参考文献：
  名称：

  Synthesis of antimicrobial glucosamides as bacterial quorum sensing mechanism inhibitors

  摘要：

  Bacteria communicate with one another and regulate their pathogenicity through a phenomenon known as quorum sensing (QS). When the bacterial colony reaches a threshold density, the QS system induces the production of virulence factors and the formation of biofilms, a powerful defence system against the host's immune responses. The glucosamine monomer has been shown to disrupt the bacterial QS system by inhibiting autoinducer (AI) signalling molecules such as the acyl-homoserine lactones (AHLs). In this study, the synthesis of acetoxy-glucosamides 8, hydroxy-glucosamides 9 and 3-oxo-glucosamides 12 was performed via the 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC center dot HCl) and N, N'-dicyclohexylcarbodiimide (DCC) coupling methods. All of the synthesized compounds were tested against two bacterial strains, P. aeruginosa MH602 (LasI/R-type QS) and E. coli MT102 (LuxI/R-type QS), for QS inhibitory activity. The most active compound 9b showed 79.1% QS inhibition against P. aeruginosa MH602 and 98.4% against E. coli MT102, while compound 12b showed 64.5% inhibition against P. aeruginosa MH602 and 88.1% against E. coli MT102 strain at 2 mM concentration. The ability of the compounds to inhibit the production of the virulence factor pyocyanin and biofilm formation in the P. aeruginosa (PA14) strain was also examined. Finally, computational docking studies were performed with the LasR receptor protein. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.12.024

文献信息

• Multi-catalysis cascade reactions based on the methoxycarbonylketene platform: diversity-oriented synthesis of functionalized non-symmetrical malonates for agrochemicals and pharmaceuticals
  作者：Dhevalapally B. Ramachary、Chintalapudi Venkaiah、Y. Vijayendar Reddy、Mamillapalli Kishor

  DOI：10.1039/b901652j

  日期：——

  In this paper we describe new multi-catalysis cascade (MCC) reactions for the one-pot synthesis of highly functionalized non-symmetrical malonates. These metal-free reactions are either five-step (olefination/hydrogenation/alkylation/ketenization/esterification) or six-step (olefination/hydrogenation/alkylation/ketenization/esterification/alkylation), and employ aldehydes/ketones, Meldrum's acid, 1,4-dihydropyridine/o-phenylenediamine, diazomethane, alcohols and active ethylene/acetylenes, and involve iminium-, self-, self-, self- and base-catalysis, respectively. Many of the products have direct application in agricultural and pharmaceutical chemistry.

  在本文中，我们描述了一种新的多重催化级联反应（MCC），用于一锅合成高度功能化的非对称马来酸酯。这些无金属催化反应分为五步（烯化/加氢/烷基化/酮化/酯化）或六步（烯化/加氢/烷基化/酮化/酯化/烷基化），涉及醛/酮、梅尔德伦酸、1,4-二氢吡啶/邻苯二胺、重氮甲烷、醇以及活性乙烯/炔烃，分别涉及亚胺、各自、自我、自我和碱催化。许多产品在农业和制药化学中具有直接应用。
• A Missing Link in Multisubstituted Pyrrolidines: Remote Stereocontrol Forged by Rhodium‐Alkyl Nitrene
  作者：Xinxin Tang、Raj K. Tak、Hidetoshi Noda、Masakatsu Shibasaki

  DOI：10.1002/anie.202212421

  日期：2022.11.21

  discovery together with the dearth of methods for synthesizing multisubstituted heterocycles with nonadjacent stereocenters, we report the stereoselective synthesis of remotely decorated, trisubstituted β-prolines via Rh-catalyzed C−H amination. The present protocol addresses the prevalent limitations associated with substituted pyrrolidines.

  鉴于吡咯烷在药物发现中的重要性以及缺乏合成具有非相邻立体中心的多取代杂环的方法，我们报告了通过 Rh 催化的 C−H 胺化立体选择性合成远程修饰的三取代 β-脯氨酸。本协议解决了与取代吡咯烷相关的普遍限制。
• 7-Beta-(Ketooximinoacylamido)-ceph-3-em-4-carbonsäurederivate, Verfahren zur Herstellung derselben und diese enthaltende Arzneimittel
  申请人：I. S. F. Società per Azioni

  公开号：EP0054970B1

  公开（公告）日：1985-07-17
• Strahlungsempfindliche Polymere mit 2-Diazo-1,3-dicarbonyl-Gruppen, Verfahren zu deren Herstellung und Verwendung in einem positiv arbeitenden Aufzeichnungsmaterial
  申请人：HOECHST AKTIENGESELLSCHAFT

  公开号：EP0501294B1

  公开（公告）日：1994-10-26
• PROCESS FOR PREPARING BETA-KETOESTER FRAGRANCE PRO-ACCORDS FROM 1,3-DIOXAN-4,6-DIONES
  申请人：THE PROCTER & GAMBLE COMPANY

  公开号：EP1023260A1

  公开（公告）日：2000-08-02