(S)-甲基 5-氧代四氢呋喃-2-羧酸 | 21461-85-8

• 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: (S)-甲基 5-氧代四氢呋喃-2-羧酸
• 中文别名: (S)-甲基5-氧代四氢呋喃-2-羧酸
• 英文名称: methyl (S)-5-oxo-tetrahydrofuran-2-carboxylate
• 英文别名: (S)-5-(methoxycarbonyl)tetrahydrofuran-2-one；(S)-methyl 5-oxotetrahydrofuran-2-carboxylate；methyl (2S)-5-oxooxolane-2-carboxylate
• CAS: 21461-85-8
• 化学式: C₆H₈O₄
• 分子量: 144.127
• InChiKey: AFHPZLNLFDYSTG-BYPYZUCNSA-N

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
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  (S)-甲基 5-氧代四氢呋喃-2-羧酸 在 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 methyl (S)-5-[(E)-cyanomethylidene]-2-oxotetrahydrofuran-5-carboxylate
  参考文献：
  名称：

  通过1,3-偶极环加成反应合成螺内酯（S）-3-[（E）-氰基亚甲基] -2-氧代四氢呋喃-5-羧酸甲酯

  摘要：

  在其75岁生日之际献给名誉教授MihaTišler

  DOI：

  10.1002/jhet.5570390227
• 作为产物：
  描述：

  alpha-酮戊二酸 在 sodium tetrahydroborate 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 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

文献信息

• Stereoselective Amination of 5-Substituted γ-Lactones and γ-Lactams – A Convenient Route for the Preparation of 5-Substituted (3S,5S)-3-Acetylaminotetrahydrofuran-2-ones and (3S,5S)-3-Acetylaminopyrrolidin-2-ones
  作者：Marko S'kof、Jurij Svete、Matej Kmetič、Simona Golič-Grdadolnik、Branko Stanovnik

  DOI：10.1002/(sici)1099-0690(199907)1999:7<1581::aid-ejoc1581>3.0.co;2-2

  日期：1999.7

  5-Substituted (S)-tetrahydrofuran-2-ones (1a,b) and (S)-pyrrolidin-2-ones (1c,d) were transformed in three steps, by treatment with tert-butoxybis(dimethylamino)methane (Bredereck's reagent), followed by nitrosation and stereoselective catalytic hydrogenation, into the corresponding 5-substituted (3S,5S)-3-acetylaminotetrahydrofuran-2-ones (4a,b) and (3S,5S)-3-acetylaminopyrrolidin-2-ones (4c,d).

  5-取代的 (S)-四氢呋喃-2-酮 (1a,b) 和 (S)-吡咯烷-2-酮 (1c,d) 通过用叔丁氧基双（二甲氨基）甲烷（Bredereck's试剂），然后进行亚硝化和立体选择性催化氢化，生成相应的 5-取代 (3S,5S)-3-乙酰氨基四氢呋喃-2-酮 (4a,b) 和 (3S,5S)-3-乙酰氨基吡咯烷-2-酮（ 4c，d）。
• 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。
• A new synthesis of alkaloid (<i>S</i>)-3-hydroxypiperidin-2-one and its<i>O</i>-TBS protected derivative
  作者：Pei-Qiang Huang、Guo Chen、Xiao Zheng

  DOI：10.1002/jhet.5570440239

  日期：2007.3

  From the known lactone (S)-4, easily derived from L-glutamic acid, a scalable approach to chiral building block O-silylated 3-hydroxypiperidin-2-one 3 and alkaloid 1 was achieved in five and six-steps respectively. The key steps are a chemoselective amidation of lactone-ester 5 and a one-pot reductive borane-decomplexation, N-debenzylation and cyclization.

  从容易衍生自L-谷氨酸的已知内酯（S）-4，分别通过五个步骤和六个步骤实现了可扩展的手性结构单元O-甲硅烷基化的3-羟基哌啶-2-酮3和生物碱1的方​​法。关键步骤是内酯5的化学选择性酰胺化反应以及一锅还原硼烷分解，N-脱苄基化和环化反应。