dimethyl 2-acetyl-3-methylpentanedioate | 219782-38-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: dimethyl 2-acetyl-3-methylpentanedioate
• 英文别名: dimethyl 2-acetyl-3-methylglutarate
• CAS: 219782-38-4
• 化学式: C₁₀H₁₆O₅
• 分子量: 216.234
• InChiKey: VBSNWVSHFIKNKB-UHFFFAOYSA-N

物化性质

• 沸点：
  277.0±20.0 °C(Predicted)
• 密度：
  1.089±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl 2-acetyl-3-methylpentanedioate 在 glucose-6-phosphate dehydrogenase 、 Α-D-吡喃葡萄糖6-磷酸 、 bakers' yeast keto ester reductase-I 、 还原型辅酶II(NADPH)四钠盐 作用下， 以 various solvent(s) 为溶剂， 生成 (2R,3R)-2-((S)-1-Hydroxy-ethyl)-3-methyl-pentanedioic acid dimethyl ester
  参考文献：
  名称：

  从面包酵母中不对称合成具有三个连续手性中心的β-羟基酯与还原酶

  摘要：

  已经研究了来自面包师酵母的具有还原酶的具有三个连续手性中心的2-烷基-3-羟基丁酸甲酯的不对称合成。当该酶用于还原在α-位被仲烷基取代的β-酮酯时，该反应以优异的立体选择性提供了相应的β-羟基酯。

  DOI：

  10.1016/s0040-4039(98)02102-9
• 作为产物：
  描述：

  巴豆酸甲酯 、 乙酰乙酸甲酯 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 72.0h， 以66%的产率得到dimethyl 2-acetyl-3-methylpentanedioate
  参考文献：
  名称：

  Chemoenzymatic Synthesis of Glutamic Acid Analogues:  Substrate Specificity and Synthetic Applications of Branched Chain Aminotransferase from Escherichia coli

  摘要：

  [GRAPHICS]A new route to alpha-keto acids is described, based on the ozonolysis of enol acetates obtained from alpha-substituted beta-keto esters. Escherichia coli branched chain aminotransferase (BCAT) activity toward a variety of substituted 2-oxoglutaric acids was demonstrated analytically. BCAT was shown to have a broad substrate spectrum, complementary to that of aspartate aminotransferase, and to offer access to a variety of glutamic acid analogues. The usefulness of BCAT was demonstrated through the synthesis of several 3- and 4-substituted derivatives.

  DOI：

  10.1021/jo070805q

文献信息

• Asymmetric Synthesis of α-Keto Esters via Cu(II)-Catalyzed Aerobic Deacylation of Acetoacetate Alkylation Products: An Unusually Simple Synthetic Equivalent to the Glyoxylate Anion Synthon
  作者：Kimberly M. Steward、Jeffrey S. Johnson

  DOI：10.1021/ol200649u

  日期：2011.5.6

  alpha-keto esters is described using a copper(II)-catalyzed aerobic deacylation of substituted acetoacetate esters. The substrates for the title process arise from catalytic, enantioselective conjugate additions and alkylation reactions of acetoacetate esters. The mild conditions do not induce racemization of the incipient enolizable alpha-keto ester. The reaction is tolerant of esters, certain ketones

  使用取代的乙酰乙酸酯的铜（II）催化的好氧脱酰作用，描述了一种简单有效的制备β-立体异构α-酮酯的方法。标题方法的底物来自乙酰乙酸酯的催化，对映选择性共轭加成和烷基化反应。温和的条件不引起初始可烯醇化的α-酮酯的外消旋化。该反应可耐受酯，某些酮，缩酮和硝基，并利用廉价，易得的材料。
• Chemoenzymatic Synthesis of Glutamic Acid Analogues:  Substrate Specificity and Synthetic Applications of Branched Chain Aminotransferase from <i>Escherichia coli</i>
  作者：Mo Xian、Sébastien Alaux、Emmanuelle Sagot、Thierry Gefflaut

  DOI：10.1021/jo070805q

  日期：2007.9.1

  [GRAPHICS]A new route to alpha-keto acids is described, based on the ozonolysis of enol acetates obtained from alpha-substituted beta-keto esters. Escherichia coli branched chain aminotransferase (BCAT) activity toward a variety of substituted 2-oxoglutaric acids was demonstrated analytically. BCAT was shown to have a broad substrate spectrum, complementary to that of aspartate aminotransferase, and to offer access to a variety of glutamic acid analogues. The usefulness of BCAT was demonstrated through the synthesis of several 3- and 4-substituted derivatives.
• Asymmetric synthesis of β-hydroxy esters having three consecutive chiral centers with a reductase from bakers' yeast
  作者：Yasushi Kawai、Kouichi Hida、Duc Hai Dao、Atsuyoshi Ohno

  DOI：10.1016/s0040-4039(98)02102-9

  日期：1998.12

  Asymmetric synthesis of methyl 2-alkyl-3-hydroxybutanoate having three consecutive chiral centers with a reductase from bakers' yeast has been investigated. When the enzyme is employed in the reduction of a β-keto ester substituted by a secondary alkyl group at α-position, the reaction affords the corresponding β-hydroxy ester in excellent stereoselectivity.

  已经研究了来自面包师酵母的具有还原酶的具有三个连续手性中心的2-烷基-3-羟基丁酸甲酯的不对称合成。当该酶用于还原在α-位被仲烷基取代的β-酮酯时，该反应以优异的立体选择性提供了相应的β-羟基酯。