3-[2-(2-hydroxyethoxy)ethoxycarbonyl]propanoic acid | 24502-36-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-[2-(2-hydroxyethoxy)ethoxycarbonyl]propanoic acid
• 英文别名: diethyleneglycol succinate；Diethylene glycol succinate；4-[2-(2-hydroxyethoxy)ethoxy]-4-oxobutanoic acid
• CAS: 24502-36-1
• 化学式: C₈H₁₄O₆
• 分子量: 206.196
• InChiKey: SJIWUNNSRFWATG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  14
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-[2-(2-benzyloxyethoxy)ethoxycarbonyl]propanoic acid 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以67%的产率得到3-[2-(2-hydroxyethoxy)ethoxycarbonyl]propanoic acid
  参考文献：
  名称：

  New propanoyloxy derivatives of 5β-cholan-24-oic acid as drug absorption modifiers

  摘要：

  A series of final twelve propanoyloxy derivatives of 5 beta-cholan-24-oic acid (O-propanoyl derivatives of cholic acid) as potential drug absorption modifiers (skin penetration enhancers, intestinal absorption promoters) was generated by multistep synthesis. Structure confirmation of all generated compounds was accomplished by H-1 NMR, C-13 NMR, IR and MS spectroscopy methods. All the prepared compounds were analyzed using RP-TLC, and their lipophilicity (R-M) was determined. The hydrophobicity (log P), solubility (log S), polar surface area (PSA) and molar volume (MV) of the studied compounds were also calculated. All the target compounds were tested for their in vitro transdermal. penetration effect and as potential intestinal absorption enhancers. The cytotoxicity of all the evaluated compounds was evaluated against normal human skin fibroblast cells. Their anti-proliferative activity was also assessed against human cancer cell lines: T-lymphoblastic leukemia cell line and breast adenocarcinoma cell line. One compound showed selective cytotoxicity against human skin fibroblast cells and another compound possessed the highest cytotoxicity against all the tested cell lines. Only one compound expressed anti-proliferative effect on leukemia cancer cells without affecting the growth of normal cells, which should be promising in potential development of new drugs. Most of the target compounds showed minimal anti-proliferative activity (IC50 > 37 mu M), indicating they would have moderate cytotoxicity when administered as chemical absorption modifiers. The relationships between the lipophilicity/polarity and the chemical structure of the studied compounds as well as the relationships between their chemical structure and enhancement effect are discussed in this article. (C) 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2013.02.001

文献信息

• CERIA SUPPORTED PALLADIUM/CALCIUM CATALYST FOR HYDROGENATING CO2 TO DIMETHYL ETHER
  申请人：King Abdulaziz University

  公开号：US20200129960A1

  公开（公告）日：2020-04-30

  Catalysts for hydrogenation of CO 2 to dimethyl ether. These catalysts comprise 0.1-10 wt % per total catalyst weight of a catalytic material containing Pd (e.g. metallic palladium), 0.05-5 wt % per total catalyst weight of a promoter containing Ca (e.g. metallic calcium), as well as 85-99 wt % of CeO 2 as a catalyst support. Methods of preparing and characterizing the catalysts as well as processes for catalyzing the hydrogenation of CO 2 to dimethyl ether and other byproducts such as methanol, carbon monoxide, and methane portrayed by reactant conversion., product selectivity, and catalyst stability are disclosed.

  CO2转化为二甲醚的加氢催化剂。这些催化剂包括含有Pd（例如金属钯）的催化材料，按照总催化剂重量的0.1-10重量％，含有Ca（例如金属钙）的助剂，按照总催化剂重量的0.05-5重量％，以及CeO2作为催化剂支撑物的85-99重量％。公开了制备和表征催化剂的方法，以及用于催化CO2转化为二甲醚和其他副产品（如甲醇、一氧化碳和甲烷）的过程，通过反应物转化率、产物选择性和催化剂稳定性描绘。
• BIOFUELS PRODUCTION FROM BIO-DERIVED CARBOXYLIC-ACID ESTERS
  申请人：Archer Daniels Midland Company

  公开号：US20170044086A1

  公开（公告）日：2017-02-16

  A process for producing biofuels compounds directly from carboxylic acid esters recovered from a fermentation system is described. The process involves taking a fermentation broth that has been reduced to a dry powder containing free organic acids; reacting the carboxylic acid in the powder with an alcohol solvent under a CO 2 -containing atmosphere in substantial absence of any other acid catalyst at a reaction temperature and pressure that corresponds to supercritical, critical or near critical conditions for at least one of the alcohol or CO 2 to synthesize an ester, then subjecting the ester to either hydrogenolysis or hydrogenation to form a biofuel.

  描述了一种直接从从发酵系统中回收的羧酸酯生产生物燃料化合物的过程。该过程涉及采取已经被还原为含有自由有机酸的干粉的发酵液；在含有CO2的气氛下，在几乎没有任何其他酸催化剂的条件下，以相应于至少一种醇或CO2的超临界、临界或接近临界条件的反应温度和压力中，将粉末中的羧酸与醇溶剂反应以合成酯，然后将酯经过氢解或加氢处理以形成生物燃料。
• Vanadium oxide catalyst supported on CeO2—ZrO2 for dimethyl ether production via oxidative dehydration of methanol
  申请人：King Abdulaziz University

  公开号：US10124320B1

  公开（公告）日：2018-11-13

  A catalyst of vanadium oxide supported on cerium oxide and zirconium oxide is specified. The catalyst comprises 0.1-10 wt % vanadium oxide relative to the total catalyst weight, and the catalyst is in the form of microparticles. A method using a wetness impregnation technique to produce the catalyst is described. The use of the catalyst in the oxidative dehydration of methanol to produce dimethyl ether is specified, along with the catalyst's stability for reaction periods of 50 or more hours.

  指定了一种支持在氧化铈和氧化锆上的钒氧化物催化剂。该催化剂相对于总催化剂重量含有0.1-10重量％的钒氧化物，并且催化剂呈微粒形式。描述了使用湿润浸渍技术生产催化剂的方法。指定了在甲醇氧化脱水制备二甲醚中使用催化剂，以及催化剂在反应周期为50小时或更长时间内的稳定性。
• Production of butyrolactone
  申请人：DAVY McKEE (LONDON) LIMITED

  公开号：EP0018162A1

  公开（公告）日：1980-10-29

  Butyrolactone is produced by oxidizing an aldehyde-ether of the general formula: wherein R, and R2 each, independently of the other, represent a C, to C4 alkyl radical, and R3 and R4 each, independently of the other, represent a hydrogen atom or a C, to C3 alkyl radical, or wherein R, represents a C, to C4 alkyl radical, R2 and R3 together with the carbon atoms to which they are attached form a 5-membered or 6-membered cycloaliphatic ring, and R4 represents a hydrogen atom or a C, to C3 alkyl radical, to form an acid ether of the general formula: followed by deetherification, dehydration and cyclization. Oxidation can be carried out with e.g. gaseous oxygen. Deetherification can be accomplished by contact with an acid catalyst, whilst cyclization may occur spontaneously. A cyclic process is described in which allyl alcohol is converted by reaction with a suitable olefin, e.g. iso-butylene, to an allyl ether of a tertiary alcohol, e.g. allyl t-butyl ether, which is then hydroformylated to form the compound of formula (I), whilst the olefin, e.g. iso-butylene, released on deetherification of the acid ether of formula (II), is recycled to the allyl ether formation step.

  丁内酯是通过氧化通式如下的醛醚而制得的： 其中 R 和 R2 各自独立地代表一个 C 至 C4 烷基，R3 和 R4 各自独立地代表一个氢原子或一个 C 至 C3 烷基，或其中 R 代表一个 C 至 C4 烷基，R2 和 R3 与它们所连接的碳原子一起形成一个 5 元或 6 元环脂族环，R4 代表一个氢原子或一个 C 至 C3 烷基，形成通式的酸醚： 然后进行脱醚、脱水和环化反应。氧化作用可以用气态氧气等进行。脱醚可以通过与酸催化剂接触来完成，而环化则可能自发发生。描述了一种循环工艺，其中烯丙基醇通过与合适的烯烃（如异丁烯）反应转化为叔醇的烯丙基醚（如烯丙基叔丁基醚），然后进行氢甲酰化反应生成式（I）化合物，而式（II）酸醚脱醚反应释放的烯烃（如异丁烯）被回收至烯丙基醚形成步骤。
• Production of tetrahydrofuran
  申请人：DAVY McKEE (LONDON) LIMITED

  公开号：EP0018164A1

  公开（公告）日：1980-10-29

  Tetrahydrofuran is produced by converting allyl alcohol to an allyl t-alkyl or -cycloalkyl ether of the general formula: 1 wherein R, and R2 each, independently of the other, represent a C1 to C4 alkyl radical, and R3 and R4 each, independently of the other, represent a hydrogen atom or a C1 to C3 alkyl radical, or wherein R1 represents a C1 to C4 alkyl radical, R2 and R3 together with the carbon atoms to which they are attached form a 5-membered or 6-membered cycloaliphatic ring, and R4 represents a hydrogen atom or a C1 to C3 alkyl radical, followed by reacting resulting compound of formula (III) under hydroformylation conditions with carbon monoxide and hydrogen in the presence of a hydroformylation catalyst to form a corresponding aldehyde-ether of the general formula: reducing resulting aldehyde-ether of the general formula (I) a corresponding hydroxy-ether of the general formula: and cleaving resulting hydroxy-ether of the general formula (II) under dehydrating conditions to produce tetrahydrofuran. Typically R1 and R2 each represent a methyl group whilst R3 and R4 each represent a hydrogen atom. The alkene of the general formula: released upon cleavage of the hydroxy-ether of formula (II) can be recycled for reaction with further allyl alcohol to form a further guantity of the ether of the general formula (III).

  四氢呋喃是通过将烯丙基醇转化为通式如下的 t-烷基或环烷基烯丙基醚而制得的： 1 其中R和R2各自独立地代表一个C1至C4烷基，R3和R4各自独立地代表一个氢原子或一个C1至C3烷基，或其中R1代表一个C1至C4烷基，R2和R3与它们所连接的碳原子一起形成一个5元或6元环脂族环、和 R4 代表氢原子或 C1 至 C3 烷基，然后在氢甲酰化催化剂存在下，在氢甲酰化条件下使得到的式 (III) 化合物与一氧化碳和氢反应，生成相应的通式醛醚： 将得到的通式(I)醛醚还原成相应的通式羟基醚： 并在脱水条件下裂解得到通式（II）的羟基醚，生成四氢呋喃。通常 R1 和 R2 各代表一个甲基，而 R3 和 R4 各代表一个氢原子。通式中的烯烃 式（II）的羟基醚裂解后释放出的烯烃可以回收利用，与更多的烯丙基醇反应生成更多的通式（III）的醚。