2-羟基戊二酸二乙酯 | 69134-53-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 2-羟基戊二酸二乙酯
• 中文别名: 2-羟基-戊二酸1,5-二乙酯
• 英文名称: diethyl 2-hydroxyglutarate
• 英文别名: diethyl 2-hydroxypentanedioate
• CAS: 69134-53-8
• 化学式: C₉H₁₆O₅
• 分子量: 204.223
• InChiKey: DYLHSDCNOUDICA-UHFFFAOYSA-N

物化性质

• 沸点：
  128-130 °C(Press: 5 Torr)
• 密度：
  1.1527 g/cm3(Temp: 30 °C)
• 溶解度：
  氯仿（微溶）、甲醇（微溶）
• LogP：
  0.920 (est)
• 保留指数：
  2195

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  2-羟基戊二酸二乙酯 在 对甲苯磺酸 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 0.5h， 生成 5-氧代四氢呋喃-2-羧酸乙酯
  参考文献：
  名称：

  减少微生物的立体化学控制。第31部分：在选定的反应条件下通过面包酵母还原2-氧代-4-芳基丁酸烷基酯

  摘要：

  已证明在水-有机溶剂中用苯甲酰氯处理面包酵母是抑制α-羟基酯还原中提供α-羟基酯的（S）-对映异构体的酶的有效方法。该方法对于全细胞系统生产具有高化学产率和高对映体过量的（R）产物是有效的。

  DOI：

  10.1016/s0957-4166(98)00277-8
• 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 2-羟基戊二酸二乙酯
  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。
• Stereochemistry of the Methyl Group in (R)-3-Methylitaconate Derived by Rearrangement of 2-Methylideneglutarate Catalysed by a Coenzyme B12-Dependent Mutase
  作者：Daniele Ciceri、Antonio J. Pierik、Günter Hartrampf、Gerd Bröker、Giovanna Speranza、Wolfgang Buckel、Sir John Cornforth、Bernard T. Golding

  DOI：10.1002/1522-2675(20000906)83:9<2550::aid-hlca2550>3.0.co;2-c

  日期：2000.9.6

  group of 3-methylitaconate has been probed using a `chiral methyl group'. The methyl group in 3-([2H1,3H]methyl)itaconate derived from either (R)- or (S)-2-methylidene[3-2H1,3-3H1]glutarate was a 50 : 50 mixture of (R)- and (S)-forms. It is concluded that the barrier to rotation about the C−C bond between the methylene radical centre and adjacent C-atom in the product-related radical [.CH2CH(−O2CC=CH2)CO2−]

  2-亚甲基戊二酸变位酶是一种腺苷钴胺素（辅酶 B12）依赖性酶，可催化 2-亚甲基戊二酸与 (R)-3-甲基衣康酸的平衡。该反应被认为是通过源自底物和产物的与蛋白质结合的自由基发生的。已经使用“手性甲基”探测了 3-甲基衣康酸酯的甲基形成的立体化学。衍生自 (R)- 或 (S)-2-亚甲基[3-2H1,3-3H1]戊二酸的 3-([2H1,3H]甲基)衣康酸酯中的甲基是 (R) 的 50 : 50 混合物- 和 (S) 形式。得出的结论是，产物相关自由基 [. CH(-O2CC=CH2)CO2-] 中亚甲基自由基中心和相邻 C 原子之间的 C-C 键的旋转势垒相对较低，并且相互作用含有 cob(II)alamin 的自由基是最小的。因此，
• A New and Facile Method for the Direct Preparation of α-Hydroxycarboxylic Acid Esters from α,β-Unsaturated Carboxylic Acid Esters with Molecular Oxygen and Phenylsilane Catalyzed by Bis(dipivaloylmethanato)manganese(II) Complex
  作者：Satoshi Inoki、Koji Kato、Shigeru Isayama、Teruaki Mukaiyama

  DOI：10.1246/cl.1990.1869

  日期：1990.10

  bis(dipivaloylmethanato)manganese(II) complex, the oxygenation of benzyl crotonate with molecular oxygen and phenylsilane proceeds smoothly under a mild condition to give benzyl 2-hydroxybutyrate in high yield. The reaction provides a new and convenient method for the direct preparation of various α-hydroxycarboxylic acid esters starting from α,β-unsaturated carboxylic acid esters. The influence of substituents

  在催化量的双(二新戊酰基甲烷)锰(II)配合物存在下，巴豆酸苄酯与分子氧和苯基硅烷的氧化反应在温和条件下顺利进行，得到高产率的2-羟基丁酸苄酯。该反应为以α,β-不饱和羧酸酯为原料直接制备各种α-羟基羧酸酯提供了一种新的方便的方法。还研究了烯烃取代基对区域选择性的影响。
• A biomimetic synthesis of polycyclic polyoxygenated aromatic compounds via polyketides
  作者：Masahiko Yamaguchi、Koichi Hasebe、Toru Minami

  DOI：10.1016/s0040-4039(00)84540-2

  日期：——

  Polyoxygenated naphthalenes, anthracenes and a naphthacene are synthesized from glutarates and acetoacetate dianion via polyketides.

  由戊二酸酯和乙酰乙酸二酯经聚酮化合物合成多氧化萘，蒽和并四苯。
• The Chemistry of Phosphapeptides: Investigations on the Synthesis of Phosphonamidate, Phosphonate, and Phosphinate Analogs of Glutamyl-.gamma.-glutamate
  作者：William P. Malachowski、James K. Coward

  DOI：10.1021/jo00104a017

  日期：1994.12

  The synthesis of the phosphonamidate, 1d, and phosphonate, 1e, analogues of a gamma-glutamyl peptide are reported. Michaelis-Arbuzov reaction with the alkyl halide, 7b, derived from L-glutamic acid, yielded dimethyl phosphonate, 8b. Selective aminolysis of the phosphorus diester provided monomethyl phosphonic acid, 9. Utilizing the methodology developed in the accompanying paper, 9 was converted to the phosphonochloridate, 10. Subsequent reaction with diethyl glutamic acid and hydrogenation afforded the complex phosphonamidate, 1d. Mitsunobu coupling of the monomethyl phosphonic acid, 9, with diethyl 2-hydroxyglutarate, followed by hydrogenation, provided the complex mixed phosphonate, 1e.