5-氧代四氢呋喃-2-羧酸甲酯 | 3885-29-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 中文名称: 5-氧代四氢呋喃-2-羧酸甲酯
• 中文别名: 5-氧代四氢呋喃-2-甲酸甲酯
• 英文名称: (+/-)-tetrahydro-5-oxo-2-furancarboxylic acid methyl ester
• 英文别名: 4-(methoxycarbonyl)-4-butanolide；methyl 5-oxotetrahydrofuran-2-carboxylate；γ-carboxy-γ-butyrolactone methyl ester；γ-methoxycarbonyl-γ-butyrolactone；<2-Hydroxy-glutarsaeure-lacton>-methylester；γ-Butyrolacton-γ-carbonsaeure-methylester；5-oxotetrahydrofuran-2-carboxylic acid, methyl ester；γ-Methoxycarbonyl-γ-butyrolacton；γ-Carbomethoxy-γ-butyrolacton；5-Oxo-tetrahydro-furan-2-carbonsaeure-methylester；methyl 5-oxooxolane-2-carboxylate
• CAS: 3885-29-8
• 化学式: C₆H₈O₄
• 分子量: 144.127
• InChiKey: AFHPZLNLFDYSTG-UHFFFAOYSA-N

物化性质

• 沸点：
  120-126 °C(Press: 11 Torr)
• 密度：
  1.265±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2932190090

反应信息

• 作为反应物：
  描述：

  5-氧代四氢呋喃-2-羧酸甲酯 生成 (S)-甲基 5-氧代四氢呋喃-2-羧酸
  参考文献：
  名称：

  Enantiomerically pure tetrahydro-5-oxo-2-furancarboxylic esters from dialkyl 2-oxoglutarates

  摘要：

  Enantiomerically pure tetrahydro-5-oxo-2-furancarboxylic esters can be prepared either by enzymatic resolution of the racemic gamma-lactones themselves or by bioreduction with baker's yeast of dialkyl 2-oxoglutarates and subsequent cyclization of the resulting dialkyl 2-hydroxyglutarates. The best results were obtained by the former route, by which the desired compounds were isolated in high enantiomeric excess. Bioreductions were less satisfactory. In fact the hydroxyester intermediates were initially formed as racemic mixtures and their final enantiomeric enrichment was reached by asymmetric destruction, occurring in the bioreaction medium, however at the same time large amounts of alkyl 4-hydroxybutanoates were formed as side products. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00286-4
• 作为产物：
  描述：

  dimethyl α-hydroxyglutarate 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以55%的产率得到5-氧代四氢呋喃-2-羧酸甲酯
  参考文献：
  名称：

  Enantiomerically pure tetrahydro-5-oxo-2-furancarboxylic esters from dialkyl 2-oxoglutarates

  摘要：

  Enantiomerically pure tetrahydro-5-oxo-2-furancarboxylic esters can be prepared either by enzymatic resolution of the racemic gamma-lactones themselves or by bioreduction with baker's yeast of dialkyl 2-oxoglutarates and subsequent cyclization of the resulting dialkyl 2-hydroxyglutarates. The best results were obtained by the former route, by which the desired compounds were isolated in high enantiomeric excess. Bioreductions were less satisfactory. In fact the hydroxyester intermediates were initially formed as racemic mixtures and their final enantiomeric enrichment was reached by asymmetric destruction, occurring in the bioreaction medium, however at the same time large amounts of alkyl 4-hydroxybutanoates were formed as side products. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00286-4

文献信息

• Lactonization of the Oncometabolite D-2-Hydroxyglutarate Produces a Novel Endogenous Metabolite
  作者：Raffaela S. Berger、Christian J. Wachsmuth、Magdalena C. Waldhier、Kathrin Renner-Sattler、Simone Thomas、Anuhar Chaturvedi、Hans-Helmut Niller、Elisabeth Bumes、Peter Hau、Martin Proescholdt、Wolfram Gronwald、Michael Heuser、Marina Kreutz、Peter J. Oefner、Katja Dettmer

  DOI：10.3390/cancers13081756

  日期：——

  In recent years, onco-metabolites like D-2-hydroxyglutarate, which is produced in isocitrate dehydrogenase-mutated tumors, have gained increasing interest. Here, we report a metabolite in human specimens that is closely related to 2-hydroxyglutarate: the intramolecular ester of 2-hydroxyglutarate, 2-hydroxyglutarate-γ-lactone. Using 13C5-L-glutamine tracer analysis, we showed that 2-hydroxyglutarate is the endogenous precursor of 2-hydroxyglutarate-lactone and that there is a high exchange between these two metabolites. Lactone formation does not depend on mutated isocitrate dehydrogenase, but its formation is most probably linked to transport processes across the cell membrane and favored at low environmental pH. Furthermore, human macrophages showed not only striking differences in uptake of 2-hydroxyglutarate and its lactone but also in the enantiospecific hydrolysis of the latter. Consequently, 2-hydroxyglutarate-lactone may play a critical role in the modulation of the tumor microenvironment.

  近年来，像D-2-羟基戊二酸这样的肿瘤代谢产物，它是在异柠檬酸脱氢酶突变肿瘤中产生的，引起了越来越多的关注。在这里，我们报告了人体标本中与2-羟基戊二酸密切相关的一种代谢产物：2-羟基戊二酸的分子内酯，2-羟基戊二酸-γ-内酯。使用13C5-L-谷氨酰胺示踪分析，我们表明2-羟基戊二酸是2-羟基戊二酸内酯的内源前体，并且这两种代谢产物之间存在高度交换。内酯的形成并不依赖于突变的异柠檬酸脱氢酶，但其形成很可能与细胞膜之间的转运过程有关，并且在低环境pH下更为有利。此外，人类巨噬细胞不仅在对2-羟基戊二酸及其内酯的摄取上存在显著差异，而且在对后者的对映选择性水解上也存在差异。因此，2-羟基戊二酸内酯可能在调节肿瘤微环境中发挥关键作用。
• Metal-catalyzed reductive deamination of glutamic acid to bio-based dimethyl glutarate and methylamines
  作者：Free De Schouwer、Thomas Cuypers、Laurens Claes、Dirk E. De Vos

  DOI：10.1039/c6gc03222b

  日期：——

  Glutamic acid is a promising renewable platform molecule which is abundantly available in biomass waste streams; it is also efficiently manufactured by fermentation. Here we report the reductive deamination of...

  谷氨酸是一种有前途的可再生平台分子，可在生物质废物流中大量使用。它也可以通过发酵有效地制造。在这里，我们报告...的还原性脱氨作用。
• LiNTf₂-Catalyzed Aminolysis of Lactones with Stoichiometric Quantities of Amines
  作者：Antonio Guarna、Claudia Lalli、Andrea Trabocchi、Gloria Menchi

  DOI：10.1055/s-2007-1000882

  日期：2008.1

  LiNTf2 in the reaction of lactones with amines is able to activate cyclic esters towards ring opening, thus leading to clean open-chain amides under mild conditions and using a stoichiometric amount of amine. The generality of the method was demonstrated by a range of selected lactones and amines.

  在内酯与胺的反应中，LiNTf2 能够活化环酯，使其向开环方向发展，从而在温和的条件下，使用一定量的胺就能生成干净的开链酰胺。一系列选定的内酯和胺证明了该方法的通用性。
• 2-Oxo-1, 3-dioxolane-4-carboxylic Acid and Derivatives Thereof, Their Preparation and Use
  申请人：Construction Research & Technology GmbH

  公开号：US20140228583A1

  公开（公告）日：2014-08-14

  2-Oxo-1,3-dioxolane-4-carboxylic acid and derivatives thereof, according to the following formula, in which R 1 represents a negative charge, hydrogen or may be methyl or ethyl or an n-valent radical, which may be substituted with at most n−1 further 2-oxo-1,3-dioxolane-4-carboxyl groups, as well as a process for their preparation by means of carboxylation of the corresponding epoxides, a process for their transesterification and their use for the preparation of hydroxyurethanes and as end groups for the blocking of amines.

  2-氧代-1,3-二氧杂环戊烷-4-羧酸及其衍生物，符合以下公式，其中R1代表负电荷、氢或甲基或乙基或n价基团，该基团可用最多n-1个进一步的2-氧代-1,3-二氧杂环戊烷-4-羧酸基团取代，以及通过相应环氧化物的羧化反应制备它们的方法，它们的转酯化反应制备方法以及它们用于制备羟基脲和作为阻止胺基团的末端基团的用途。
• Verfahren zur Herstellung von 5-Ringheterocyclen
  申请人：BASF Aktiengesellschaft

  公开号：EP0602515A1

  公开（公告）日：1994-06-22

  Verfahren zur Herstellung von 5-Ringheterocyclen der allgemeinen Formel I in der R¹Methyl oder Hydroxyethyl, R²,R³,R⁴,R⁵,R⁶Wasserstoff, C₁- bis C₁₂-Alkyl, C₂- bis C₁₂-Alkenyl, Aryl, C₃- bis C₈-Cycloalkyl, C₁- bis C₁₂-Alkoxy, Halogen, C₂- bis C₂₀-Alkoxycarbonyl-alkyl, C₂-bis C₂₀-Alkylcarbonyloxy, Formyl, C₂- bis C₂₀-Formylalkyl, Benzoyl, -CH (OR³) (OR⁵) oder R³ und R⁵ gemeinsam eine gegebenenfalls ein- bis fünffach durch R⁴ substituierte C₂- bis C₇-Alkylenkette oder eine gegebenenfalls ein- bis vierfach durch R⁴ substituierte =CH-CH=CH-CH= Einheit, XSauerstoff oder N-R⁴ bedeuten, indem man 5-Ringheterocyclen der allgemeinen Formel II in denen R² R³, R⁴, R⁵, R⁶ und X die obengenannte Bedeutung haben und Y Wasserstoff, Acetyl oder C₂- bis C₂₀-Alkoxycarbonyl bedeutet, mit Dimethyl- oder Ethylencarbonat in Gegenwart einer stickstoffhaltigen Base bei Temperaturen von 50 bis 300°C und Drücken von 0,01 bis 50 bar umsetzt.

  通式 I 的 5 环杂环的制备工艺 在 R¹甲基或羟乙基、 R²,R³,R⁴,R⁵,R⁶氢、C₁- 至 C₁₂- 烷基、C₂- 至 C₁₂- 烯基、芳基、C₃- 至 C₈ 环烷基、C₁- 至 C₁₂- 烷氧基、卤素，C₂- 至 C₂₀-烷氧基羰基烷基，C₂- 至 C₂₀-烷基羰氧基，甲酰基，C₂- 至 C₂₀-甲酰基烷基、苯甲酰基、-CH (OR³) (OR⁵) 或 R³ 和 R⁵ 共同形成被 R⁴ 任选取代一至五次的 C₂- 至 C₇- 亚烷基链，或被 R⁴ 任选取代一至四次的 =CH-CH=CH-CH= 单元、 X-氧或 N-R⁴ 使通式 II 的 5 环杂环反应 其中，R² 表示 R³，R⁴、R⁵、R⁶ 和 X 具有上述含义，Y 表示氢、乙酰基或 C₂- 至 C₂₀- 烷氧基羰基，与碳酸二甲酯或碳酸乙烯酯在含氮碱存在下，在温度 50 至 300°C 和压力 0.01 至 50 巴下反应。