3,6-diethyltetrahydro-2H-pyran-2-one | 16429-10-0

• 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: 3,6-diethyltetrahydro-2H-pyran-2-one
• 英文别名: 2-ethylheptan-5-olide；3,6-diethyloxan-2-one
• CAS: 16429-10-0
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: DIZRUCSLFRGRMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,6-diethyltetrahydro-2H-pyran-2-one 在 Pd/SiO₂/Al₂O₃ 、 氢气 作用下， 270.0 ℃ 、3.0 MPa 条件下， 以89%的产率得到2-乙基庚酸
  参考文献：
  名称：

  PROCESS FOR PRODUCING 2-ETHYLHEPTANOIC ACID

  摘要：

  制备2-乙基庚酸的过程。

  公开号：

  US20140194648A1
• 作为产物：
  描述：

  3-ethylidene-6-vinyltetrahydro-2H-pyran-2-one 在 0.5% Pd on alumina 、 氢气 作用下， 以 四氢呋喃 为溶剂， 60.0 ℃ 、2.0 MPa 条件下， 反应 20.0h， 以93%的产率得到3,6-diethyltetrahydro-2H-pyran-2-one
  参考文献：
  名称：

  PROCESS FOR PRODUCING 2-ETHYLHEPTANOIC ACID

  摘要：

  制备2-乙基庚酸的过程。

  公开号：

  US20140194648A1

文献信息

• SYNTHESIS OF BUILDING BLOCKS AND FEEDSTOCKS FOR MANUFACTURING RENEWABLE POLYMERS
  申请人：Qatar Foundation for Education, Science and Community Development

  公开号：US20210292266A1

  公开（公告）日：2021-09-23

  Disclosed are methods or processes of synthesizing building blocks and feedstocks for producing a broader range of polymers, including renewable polymers, from renewable resources such as CO 2 . In a process of manufacturing a renewable feedstock for polymer production, a CO 2 derived lactone is prepared and processed to form the renewable feedstock. The process may include alkoxycarbonylation of the CO 2 derived lactone to form a diester and hydrogenation of the diester.

  公开了一种从可再生资源（如CO2）合成用于生产更广泛范围的聚合物（包括可再生聚合物）的构建块和原料的方法或过程。在制造用于聚合物生产的可再生原料的过程中，首先制备并加工 衍生的内酯以形成可再生原料。该过程可能包括对 衍生的内酯进行烷氧羰基化以形成二酯，并对二酯进行氢化的步骤。
• [EN] METAL-CATALYZED ALKOXYCARBONYLATION OF A LACTONE<br/>[FR] ALCOXYCARBONYLATION CATALYSÉE PAR UN MÉTAL D'UNE LACTONE
  申请人：QATAR FOUND EDUCATION SCIENCE & COMMUNITY DEV

  公开号：WO2018175332A1

  公开（公告）日：2018-09-27

  The metal-catalyzed alkoxycarbonylation of a lactone is a method of alkoxycarbonylating a δ-lactone, specifically 3-ethylidene-6-vinyltetrahydro-2H-pyran-2-one. The method includes combining the δ-lactone with an alcohol in an organic solvent in the presence of a catalyst system that includes palladium or a salt thereof to form a reaction mixture, which is heated to 110-130˚C at a pressure of 20-50 bar for between 3-5 hours under flow of carbon monoxide gas. The product of the reaction is a substituted 2-octendioate diester. The alcohol may be methyl alcohol, n-butyl alcohol, 2-ethylhexanol, isobutyl alcohol, isopropyl alcohol, benzyl alcohol, or phenol. The solvent may be toluene, acetonitrile, or tetrahydrofuran. The method may include adding an acid to the reaction mixture, which may be dilute (about 5 mol%) sulfuric or p-toluenesulfonic acid. The catalyst system may also include a phosphine ligand.

  δ-内酯的金属催化羟羰化是一种羟羰基化δ-内酯的方法，具体是3-乙烯基-6-乙烯基四氢-2H-吡喃-2-酮。该方法包括将δ-内酯与醇在有机溶剂中与包括钯或其盐的催化剂体系一起混合，形成反应混合物，然后在20-50巴的压力下，在110-130°C下在流动一氧化碳气体的条件下进行3-5小时的加热。反应的产物是取代的2-辛二酸二酯。醇可以是甲醇、正丁醇、2-乙基己醇、异丁醇、异丙醇、苄醇或酚。溶剂可以是甲苯、乙腈或四氢呋喃。该方法可能包括向反应混合物中添加酸，该酸可以是稀释的（约5摩尔％）硫酸或对甲苯磺酸。催化剂体系还可能包括膦配体。
• Bimetallic-Catalyzed Reduction of Carboxylic Acids and Lactones to Alcohols and Diols
  作者：Arno Behr、Volker A. Brehme

  DOI：10.1002/1615-4169(200207)344:5<525::aid-adsc525>3.0.co;2-u

  日期：2002.7

  [Rh(acac)(CO)2] and [Mo(CO)6] showed the highest activity and was therefore applied to the reduction of lactones to diols. The reduction potential of the catalyst was found to be dependent on the ring size of the lactone used. Five-membered ring lactones were hardly converted to diols whereas six- and seven- membered ring lactones reacted easily.

  研究了氢对羧酸的均相催化还原反应。由第8族或第9组晚过渡金属和第二族第6或7组过渡金属羰基组成的双金属催化剂具有协同作用，可在中等条件下以高收率转化。除了不同催化剂前体的影响外，还研究了温度，氢气压力和催化剂浓度的影响。[Rh（acac）（CO）2 ]和[Mo（CO）6的等摩尔混合物]显示出最高的活性，因此适用于将内酯还原为二醇。发现催化剂的还原电势取决于所用内酯的环大小。五元环内酯几乎不转化为二醇，而六元和七元环内酯则容易反应。
• Metal-catalyzed alkoxycarbonylation of a lactone
  申请人：QATAR FOUNDATION FOR EDUCATION, SCIENCE AND COMMUNITY DEVELOPMENT

  公开号：US10519094B2

  公开（公告）日：2019-12-31

  The metal-catalyzed alkoxycarbonylation of a lactone is a method of alkoxycarbonylating a δ-lactone, specifically 3-ethylidene-6-vinyltetrahydro-2H-pyran-2-one. The method includes combining the δ-lactone with an alcohol in an organic solvent in the presence of a catalyst system that includes palladium or a salt thereof to form a reaction mixture, which is heated to 110-130° C. at a pressure of 20-50 bar for between 3-5 hours under flow of carbon monoxide gas. The product of the reaction is a substituted 2-octendioate diester. The alcohol may be methyl alcohol, n-butyl alcohol, 2-ethylhexanol, isobutyl alcohol, isopropyl alcohol, benzyl alcohol, or phenol. The solvent may be toluene, acetonitrile, or tetrahydrofuran. The method may include adding an acid to the reaction mixture, which may be dilute (about 5 mol %) sulfuric or p-toluenesulfonic acid. The catalyst system may also include a phosphine ligand.

  内酯的金属催化烷氧基羰基化是一种δ-内酯，特别是 3-亚乙基-6-乙烯基四氢-2H-吡喃-2-酮的烷氧基羰基化方法。该方法包括在包括钯或钯盐的催化剂体系存在下，在有机溶剂中将δ-内酯与醇结合，形成反应混合物，在一氧化碳气体流动下，将反应混合物加热至 110-130 摄氏度，压力为 20-50 巴，时间为 3-5 小时。反应产物为取代的 2-辛二酸二酯。醇可以是甲醇、正丁醇、2-乙基己醇、异丁醇、异丙醇、苯甲醇或苯酚。溶剂可以是甲苯、乙腈或四氢呋喃。该方法可包括向反应混合物中加入一种酸，这种酸可以是稀硫酸或对甲苯磺酸（约 5 摩尔%）。催化剂体系还可包括膦配体。
• Method for preparing delta-lactones
  申请人：Qatar Foundation For Education, Science and Community Development

  公开号：US10844033B2

  公开（公告）日：2020-11-24

  The present invention relates to methods of forming delta-lactone compounds by reaction of a diene with carbon dioxide in the presence of Pd and a phosphine ligand.

  本发明涉及在钯和膦配体存在下，通过二烯与二氧化碳反应形成δ-内酯化合物的方法。