diethyl 5-methyl-4H-1,2-oxazole-3,5-dicarboxylate | 141562-82-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: diethyl 5-methyl-4H-1,2-oxazole-3,5-dicarboxylate
• CAS: 141562-82-5
• 化学式: C₁₀H₁₅NO₅
• 分子量: 229.233
• InChiKey: WLMCNCXVTRFYTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  74.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl 5-methyl-4H-1,2-oxazole-3,5-dicarboxylate 在 镍 盐酸 、 phosphate buffer 、 氢气 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 生成 (2S,4R)-2-amino-4-hydroxy-4-methylpentanedioic acid
  参考文献：
  名称：

  化学酶法合成4-羟基-4-甲基谷氨酸的四种立体异构体

  摘要：

  描述了化学合成4-羟基-4-甲基谷氨酸的四个立体异构体。与其他谷氨酸类似物一样，这些化合物可用作研究谷氨酸受体的探针。

  DOI：

  10.1016/s0957-4166(98)00372-3
• 作为产物：
  描述：

  ethyl 2-nitro-3-oxobutyrate 、 甲基丙烯酸乙酯 在 硫酸 作用下， 以 乙酸酐 、 溶剂黄146 为溶剂， 反应 3.0h， 以63%的产率得到diethyl 5-methyl-4H-1,2-oxazole-3,5-dicarboxylate
  参考文献：
  名称：

  Ethyl 2-nitroacetoacetate as a new synthetic equivalent of ethoxycarbonylnitrile oxide

  摘要：

  It was shown that ethyl 2-nitroacetoacetate is a synthetic precursor of ethoxycarbonylnitrile oxide as well as of isoxazole- and isoxazoline-3-carboxylic acids and their esters. The elimination of acetic acid from ethyl 2-nitroacetoacetate occurs in a mixture of acetic acid and acetic anhydride in the presence of strong mineral acids, e.g., H2SO4, at room temperature and gives isoxazolines in yields of up to 85-91 %.

  DOI：

  10.1007/bf00699144

文献信息

• Chemoenzymatic Synthesis of (<i>R</i>)-(-)-Citramalic Acid
  作者：Shangjin Yang、Walter Hayden、Kurt Faber、Herfried Griengl

  DOI：10.1055/s-1992-26110

  日期：——

  Dimethyl (R)-(-)-citramalate (dimethyl 2-hydroxy-2-methylsuccinate, 4) was prepared in ≍ 50% overall yield in four steps from ethyl chloro(hydroxyimino)acetate and ethyl methacrylate. The key transformation involved a regio- and enantiospecific hydrolysis of diethyl (RS)-5-methyl-4, 5-dihydroisoxazole-3,5-dicarboxylate (1a) using a protease from Aspergillus oryzae.

  (R)-(-)-柠檬醛酸二甲酯（2-羟基-2-甲基琥珀酸二甲酯，4）由氯（羟基亚氨基）乙酸乙酯和甲基丙烯酸乙酯经四个步骤制备而成，总收率为§50%。关键的转化过程是利用一种来自黑曲霉的蛋白酶对 (RS)-5-甲基-4, 5-二氢异噁唑-3,5-二甲酸二乙酯 (1a) 进行区域和对映体特异性水解。
• Process for producing gamma-hydroxyamino acid derivatives and monatins
  申请人：AJINOMOTO, CO., INC.

  公开号：US20030228403A1

  公开（公告）日：2003-12-11

  Dihydroisoxazole derivatives are conveniently converted to &ggr;-hydroxyamino acid derivatives which are important as various synthetic intermediates by a catalytic hydrogenation reaction. High-purity monatins which may be used as sweeteners or ingredients thereof can be obtained by subjecting a 5-indolylmethyl-4,5-dihydroisoxazole-3,5-dicarboxylic acid to catalytic hydrogenation.

  二氢异噁唑衍生物可以方便地通过催化氢化反应转化为重要的&ggr;-羟基氨基酸衍生物，这些衍生物是各种合成中间体。通过将5-吲哚甲基-4,5-二氢异噁唑-3,5-二羧酸进行催化氢化，可以得到高纯度的单糖，可以用作甜味剂或其成分。
• Resolution of ?2-isoxazoline-5-carboxylates by a protease fromAspergillus Oryzae providing masked synthons for enantiopure ?-aminoalcohols and related structures
  作者：S. Yang、W. Hayden、H. Griengl

  DOI：10.1007/bf00811865

  日期：1994.4

  A series of racemic DELTA2-isoxazolinecarboxylates have been synthesized and subjected to enzymatic hydrolysis by a protease from Aspergillus oryzae in a two-phase system. Out of these compounds only isoxazoline-5-carboxylates unsubstituted at C-4 were hydrolyzed. Thus, from 3-ethoxycarbonyl-, 3-methyl-, and 3-phenyl-DELTA2-isoxazoline-5-carboxylates the corresponding (R)-configurated carboxylic acids are obtained. In contrast, an additional methyl group at C-5 changes the steric course of the hydrolysis to give predominantly the (S)-acid. The enantioselectivities obtained are in the range of E = 5-35.
• Process for converting dihydroisoxazole derivatives to gamma-hydroxyamino acid derivatives, e.g. monatins
  申请人：Ajinomoto Co., Inc.

  公开号：EP1350791B1

  公开（公告）日：2006-09-20
• Yang S., Hayden W., Griengl H., Monatsh. Chem, 125 (1994) N 4, S 469-477
  作者：Yang S., Hayden W., Griengl H.

  DOI：——

  日期：——

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