(R)-(-)-γ-乙氧羰基-γ-丁内酯 | 33019-03-3

• 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)-(-)-γ-乙氧羰基-γ-丁内酯
• 中文别名: (R)-(-)-Γ-乙氧羰基-Γ-丁内酯；(R)-(-)-5-氧四氢-2-呋喃羧酸乙酯；(R)-(-)-γ-乙氧基羰基-γ-丁内酯；(R)-(?)-γ-乙氧羰基-γ-丁内酯
• 英文名称: (R)-(-)-tetrahydro-5-oxo-2-furancarboxylic acid ethyl ester
• 英文别名: 2R-carboethoxy-5-oxo-tetrahydrofuran；Ethyl (R)-5-oxotetrahydrofuran-2-carboxylate；5-oxotetrahydrofuran-2-carboxylic acid ethyl ester；(R)-(-)-gamma-Ethoxycarbonyl-gamma-butyrolactone；ethyl (2R)-5-oxooxolane-2-carboxylate
• CAS: 33019-03-3
• 化学式: C₇H₁₀O₄
• 分子量: 158.154
• InChiKey: MJQGWRVDIFBMNW-RXMQYKEDSA-N

物化性质

• 沸点：
  151-155 °C/12 mmHg (lit.)
• 密度：
  1.163 g/mL at 25 °C (lit.)
• 闪点：
  >230 °F
• 稳定性/保质期：
  如果按照规格正确使用和储存，则不会分解，未有已知危险发生。 应避免与强氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 安全说明：
  S23,S24/25
• WGK Germany：
  3
• 海关编码：
  2932190090
• 储存条件：
  请将药品存放在密闭、阴凉干燥处保存。

反应信息

• 作为反应物：
  描述：

  (R)-(-)-γ-乙氧羰基-γ-丁内酯 在 吡啶 、 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 2,3-二甲基-2-丁烯 、 硼烷四氢呋喃络合物 、 碘代三甲硅烷 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 生成 4-氨基-5-氟-1-[(2S,5R)-5-(羟基甲基)四氢呋喃-2-基]嘧啶-2-酮
  参考文献：
  名称：

  Mansour, Tarek S.; Tse, Allan; Charron, Marie, Medicinal Chemistry Research, 1995, vol. 5, # 6, p. 417 - 425

  摘要：

  DOI：
• 作为产物：
  描述：

  5-氧代四氢呋喃-2-羧酸乙酯 生成 (R)-(-)-γ-乙氧羰基-γ-丁内酯
  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

• 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。
• Substituted imidazo[1, 2-a]-5,6,7,8-tetrahydropyridine-8-ones, method for their production and the use thereof for producing imidazo[1,2-a]pyridines
  申请人：Weigl Hagan

  公开号：US20050020620A1

  公开（公告）日：2005-01-27

  A process for the preparation of imidazo[1,2-a]-5,6,7,8-tetra hydropyridin-8-ones by reaction of γ-butyrolactones with imidazols, novel imidazo[1,2-a]-5,6,7,8-tetrahydropyridin-8-ones, and their use for the preparation of imidazo[1,2-a]pyridines are described.

  描述了通过γ-丁内酯与咪唑醇反应制备咪唑并[1,2-a]-5,6,7,8-四氢吡啶-8-酮的工艺、新型咪唑并[1,2-a]-5,6,7,8-四氢吡啶-8-酮及其在制备咪唑并[1,2-a]吡啶中的应用。
• Diastereocontrol in glycosylation reactions: Synthesis of β-D and β-L dideoxycytidine analogues
  作者：Allan Tse、Tarek S. Mansour

  DOI：10.1016/0040-4039(95)01653-y

  日期：1995.10

  Expeditious and diastereoselective total syntheses of the antiviral agents, beta-L-ddC, beta-L-5FddC and beta-D-5FddC have been achieved in four steps from commercially available R-(-)-5-oxo-2-tetrahydrofurancarboxylic and its 2S isomer respectively.
• Processes for the diastereo-selective synthesis of nucleosides
  申请人：BIOCHEM PHARMA INC.

  公开号：EP0515156B1

  公开（公告）日：1996-02-07
• US5744596A
  申请人：——

  公开号：US5744596A

  公开（公告）日：1998-04-28