2-oxabicyclo[4.5.0]undecan-3-one | 4441-65-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 2-oxabicyclo[4.5.0]undecan-3-one
• 英文别名: 4-(2'-hydroxycyclohexyl)butanoic acid lactone；octahydro-benzo[b]oxepin-2-one；1-Benzoxepin-2(3H)-one, octahydro-；4,5,5a,6,7,8,9,9a-octahydro-3H-benzo[b]oxepin-2-one
• CAS: 4441-65-0
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: JFTXZBPTXPXYOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  trans-1-decalone 在 oxone 、 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以98%的产率得到2-oxabicyclo[4.5.0]undecan-3-one
  参考文献：
  名称：

  Baeyer−Villiger Oxidation with Potassium Peroxomonosulfate Supported on Acidic Silica Gel

  摘要：

  Potassium peroxomonosulfate deposited onto silica (SiO2KHSO5)-K-. efficiently reacts with ketones in dichloromethane at room temperature to give the corresponding esters or lactones in quantitative yields. This method avoids hydrolysis of the reaction products. The Baeyer-Villiger reaction is catalyzed by potassium hydrogensulfate present in the supported reagent.

  DOI：

  10.1021/jo051614v

文献信息

• HOF·CH3CN, made directly from F2 and water, as an ecologically friendly oxidizing reagent
  作者：Shlomo Rozen、Yifat Bareket、Moshe Kol

  DOI：10.1016/s0040-4020(01)88036-4

  日期：1993.9

  The complex HOF·CH3CN, made directly from fluorine and aqueous acetonitrile, was used for oxidation of secondary alcohols and for Baeyer Villiger oxidation of ketones. By using 18O labeled reagent it was found that the ketone oxidation proceeds through the original dioxirane mechanism which Baeyer and Villiger suggested a century ago for reactions with peracids but was later discounted.

  直接由氟和乙腈水溶液制得的复合物HOF·CH 3 CN用于氧化仲醇和用于Baeyer Villiger氧化酮。通过使用18 O标记的试剂，发现酮的氧化过程是通过最初的二环氧乙烷机理进行的，Baeyer和Villiger于一个世纪前就提出了与过酸的反应，但后来又打折扣了。
• Bimetallic nanosized solids with acid and redox properties for catalytic activation of C–C and C–H bonds
  作者：Jose R. Cabrero-Antonino、María Tejeda-Serrano、Manuel Quesada、Jose A. Vidal-Moya、Antonio Leyva-Pérez、Avelino Corma

  DOI：10.1039/c6sc03335k

  日期：——

  A new approach is presented to form self-supported bimetallic nanosized solids with acid and redox catalytic properties. They are water-, air- and H2-stable, and are able to activate demanding C–C and C–H reactions. A detailed mechanistic study on the formation of the Ag–Fe bimetallic system shows that a rapid redox-coupled sequence between Ag+, O2 (air) and Fe2+ occurs, giving monodisperse Ag nanoparticles

  提出了一种形成具有酸和氧化还原催化特性的自支撑双金属纳米固体的新方法。它们对水、空气和 H 2稳定，并且能够激活要求苛刻的 C–C 和 C–H 反应。对 Ag-Fe 双金属体系形成的详细机理研究表明，Ag +、O 2（空气）和 Fe 2+之间发生快速氧化还原耦合序列，产生由 O 桥联双原子 Fe 3+支撑的单分散 Ag 纳米粒子三氟甲酰亚胺。该系统可以扩展到嵌入 Cu 2+、Bi 3+和 Yb 3+三氟甲酰亚胺基质中的银纳米颗粒。
• Block Biodegradable Copolymers for Medical Devices
  申请人：Guo Ya

  公开号：US20080107704A1

  公开（公告）日：2008-05-08

  Disclosed herein are implantable medical devices comprising controlled release biodegradable block copolymers or coated with controlled release block copolymers and at least one drug releasable from the block copolymer. The controlled release block copolymers comprise least two blocks selected from the group consisting of polyesters, polyethers, and polyurethanes.

  本文披露了植入式医疗器械，其包括具有控制释放生物可降解嵌段共聚物或涂有控制释放嵌段共聚物并且至少一种药物可从嵌段共聚物中释放的医疗器械。这些控制释放嵌段共聚物包括至少两个块，所述块选自聚酯类、聚醚类和聚氨酯类的群组。
• 5-cyclopentyl-5-hydroxypentanoic and 4-(2′-hydroxycyclohexyl)-butanoic acids lactones obtention by anodic oxidation of 1-decalone
  作者：Fructuoso Barba、Antonio Guirado、Isidoro Barba、Marcelo Lopez

  DOI：10.1016/s0040-4039(00)86861-6

  日期：——

  The 1-decalone anodic oxidation products in alkaline hydroalcoholic medium with platinum anode are identified. The 5-cyclopentyl-5-hydroxypentanoic acid lactone formation evidence a ring contraction process through a carbocationic intermediate.

  鉴定了具有铂阳极的碱性水醇介质中的1-decalone阳极氧化产物。5-环戊基-5-羟基戊酸内酯的形成证明了通过碳阳离子中间体的环收缩过程。
• Baeyer–Villiger oxidation of ketones with a silica-supported peracid in supercritical carbon dioxide under flow conditions
  作者：Rossella Mello、Andrea Olmos、Javier Parra-Carbonell、María Elena González-Núñez、Gregorio Asensio

  DOI：10.1039/b821746g

  日期：——

  ketones in supercritical carbon dioxide at 250 bar and 40 °C under flow conditions to yield the corresponding esters and lactones. The solid reagent can be easily recycled through treatment with 70% hydrogen peroxide in the presence of an acid at 0 °C. This procedure not only simplifies the isolation of the reaction products, but has the advantage of using only water and carbon dioxide as solvents

  [2-过羧乙基]-官能化的二氧化硅与 酮类 在250 bar和40°C的超临界二氧化碳中于流动条件下产生相应的 酯类 和 内酯。通过使用70％的处理剂，可以轻松回收固体试剂过氧化氢在0°C的酸存在下。该程序不仅简化了反应产物的分离，而且具有仅使用水 和二氧化碳作为 溶剂 在温和的条件下。