(R)-5-氧代四氢呋喃-2-羧酸甲酯 | 19684-04-9

• 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: (R)-5-氧代四氢呋喃-2-羧酸甲酯
• 英文名称: (R)-γ-(Methoxycarbonyl)-γ-butyrolactone
• 英文别名: (R)-(-)-tetrahydro-5-oxo-2-furancarboxylic acid methyl ester；Methyl (R)-5-oxotetrahydrofuran-2-carboxylate；(R)-(-)-5-oxo-2-tetrahydrofurancarboxylic acid methyl ester；2-(R)-5-oxotetrahydrofuran-2-carboxylic acid, methyl ester；(R)-methyl 5-oxotetrahydrofuran-2-carboxylate；methyl (2R)-5-oxooxolane-2-carboxylate
• CAS: 19684-04-9
• 化学式: C₆H₈O₄
• 分子量: 144.127
• InChiKey: AFHPZLNLFDYSTG-SCSAIBSYSA-N

物化性质

• 沸点：
  266.1±33.0 °C(Predicted)
• 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

反应信息

• 作为反应物：
  描述：

  (Z)-5-(4-Methoxyphenyl)-4-penten-1-amine 、 (R)-5-氧代四氢呋喃-2-羧酸甲酯 以 二氯甲烷 为溶剂， 反应 90.0h， 以49%的产率得到-Methyl 2-hydroxy-5-<<5-(4-methoxyphenyl)-4-pentenyl>amino>-5-oxopentanoate
  参考文献：
  名称：

  Synthesis of Chiral Hydroxylated Quinolizidines via Vinylogous Bischler-Napieralski Nitrilium Ion Cyclizations

  摘要：

  Treatment of the amido esters 9 and 17 with PPSE (polyphosphoric acid trimethylsilyl ester) followed by NaBH4 in ethanol gave the quinolizidinones 11-14 and 19 via a vinylogous Bischler-Napieralski nitrilium ion cyclization-reductive lactamization two-step process. Subsequent ozonolysis and reduction afforded chiral hydroxylated quinolizidines in moderate to good yield. In contrast to five-membered-ring formation, six-membered-ring formation via nitrilium-ion cyclization requires a p-methoxy-substituted styryl terminator. The effect para-substituted styryl terminators have on the energy of activation and Delta H for the cyclization process has been calculated by semiempirical and ab initio methods.

  DOI：

  10.1021/jo00087a026
• 作为产物：
  描述：

  alpha-酮戊二酸二甲酯 在 sodium tetrahydroborate 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 生成 (R)-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

• LIGAND-DIRECTED COVALENT MODIFICATION OF PROTEIN
  申请人：Petter Russell C.

  公开号：US20110269244A1

  公开（公告）日：2011-11-03

  The present invention relates to enzyme inhibitors. More specifically, the present invention relates to ligand-directed covalent modification of proteins; method of designing same; pharmaceutical formulation of same; and method of use.

  本发明涉及酶抑制剂。更具体地说，本发明涉及配体导向的蛋白共价修饰；相同设计方法；相同的药物配方；以及使用方法。
• Asymmetric synthesis of alkyl 5-oxotetrahydrofuran-2-carboxylates by enantioselective hydrogenation of dialkyl 2-oxoglutarates over cinchona modified Pt/Al2O3 catalysts
  作者：Katalin Balázsik、Kornél Szöri、Béla Török、Mihály Bartók

  DOI：10.1039/b000390p

  日期：——

  The first direct asymmetric synthesis of chiral alkyl 5-oxo-tetrahydrofuran-2-carboxylates (up to 96% ee), which are important building blocks in the synthesis of natural products by heterogeneous cinchona-modified Pt-catalyzed hydrogenation of α-ketoglutaric acid esters and subsequent cyclization of hydroxy esters is described.

  描述了一种直接的不对称合成手性烷基5-氧代四氢呋喃-2-羧酸酯的方法（最高达到96%的对映体过剩），这些化合物是通过异相奎宁修饰的铂催化α-酮戊二酸酯的氢化及随后羟基酯的环化反应中合成天然产物的重要构建块。
• Development of a Multigram Asymmetric Synthesis of 2-(<i>R</i>)-2-(4,7,10-Tris <i>tert</i>-Butylcarboxymethyl-1,4,7,10-tetraazacyclododec-1-yl)-pentanedioic Acid, 1-<i>tert</i>-Butyl Ester, (<i>R</i>)-<i>tert</i>-Bu₄-DOTAGA
  作者：Stuart G. Levy、Vincent Jacques、Kevin Li Zhou、Shirley Kalogeropoulos、Kelly Schumacher、John C. Amedio、Jonathan E. Scherer、Steven R. Witowski、Richard Lombardy、Karsten Koppetsch

  DOI：10.1021/op8002932

  日期：2009.5.15

  A process for the multigram asymmetric synthesis of the chiral tetraazamacrocycle 2-(R)-2-(4,7,10-tris tert-butylcarboxymethyl-1,4,7,10-tetraazacyclododec-1-yl)-pentanedioic acid, 1-tert-butyl ester ((R)-tert-Bu4-DOTAGA, 4) has been devised and demonstrated. The nine-step synthesis features an improved synthesis of 2-(S)-5-oxotetrahydrofuran-2-carboxylic acid, tert-butyl ester 8, the precursor to the

  手性四氮杂大环2-（R）-2-（4,7,10-三叔丁基丁基羧甲基-1,4,7,10-四氮杂环十二烷基-1-基）-戊二酸的多克不对称合成方法1 -叔丁基酯（（[R ）-叔-Bu 4 -DOTAGA，4）已经设计和展示。九步合成法改进了2-（S）-5-氧代四氢呋喃-2-羧酸叔丁酯8的合成，该酯是新型烷基化剂（S）-5-苄基1-叔丁基的前体2-（甲基磺酰氧基）戊二酸酯12，用于以高光学纯度将正交保护的手性谷氨酸臂引入1,4,7,10-四氮杂环十二烷（环）核。环烯衍生物（[R ）-吨-Bu 4 -DOTAGA，4，一种用于磁共振成像中的用途的关键中间体（MRI）的候选，以高化学（≥95％）和光（EE≥97％）纯度产生。开发的方法成功地应用于的千克规模的cGMP合成（- [R ） -吨-Bu 4 -DOTAGA。
• NAD(P)⁺–NAD(P)H Models. 59. 1,2- Versus 1,4-Reduction of β,γ-Unsaturated α-Keto Ester
  作者：Atsuyoshi Ohno、Tsuneo Yasuma、Kaoru Nakamura、Shinzaburo Oka

  DOI：10.1246/bcsj.59.2905

  日期：1986.9

  Depending on the reactivity of the reducing agent, β,γ-unsaturated α-keto ester is reduced into either β,γ-unsaturated α-hydroxy ester or saturated α-keto ester as the result of 1,2- or 1,4-reduction.

  根据还原剂的反应性，β,γ-不饱和α-酮酯被还原成β,γ-不饱和α-羟基酯或饱和α-酮酯作为1,2-或1,4-的结果减少。
• OHNO ATSUYOSHI; YASUMA TSUNEO; NAKAMURA KAORU; OKA SHINZABURO, BULL. CHEM. SOC. JAP., 59,(1986) N 9, 2905-2906
  作者：OHNO ATSUYOSHI、 YASUMA TSUNEO、 NAKAMURA KAORU、 OKA SHINZABURO

  DOI：——

  日期：——