3-Methyl-2-oxobutanedioic Acid 1-Ethyl 4-Methyl Ester | 99380-59-3

• 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: 3-Methyl-2-oxobutanedioic Acid 1-Ethyl 4-Methyl Ester
• 英文别名: 3-Methyl-2-oxobutanedioic acid 1-ethyl 4-methyl diester；4-Ethyl 1-methyl 2-methyl-3-oxobutanedioate；1-O-ethyl 4-O-methyl 3-methyl-2-oxobutanedioate
• CAS: 99380-59-3
• 化学式: C₈H₁₂O₅
• 分子量: 188.18
• InChiKey: KOPTWRFFQGZXCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  甲基氧代琥珀酸二甲盐 、 草酰丙酸二乙酯 生成 3-Methyl-2-oxobutanedioic Acid 1-Ethyl 4-Methyl Ester
  参考文献：
  名称：

  FITZHUGH, A. L.;STRAUSS, R. S.;BREWER, E. N.;GLASSMAN, S. D.;JONES, M. ,,+, TETRAHEDRON LETT., 1985, 26, N 33, 3911-3914

  摘要：

  DOI：

文献信息

• Reaction of small-size cycloalkane rings with RuO4. Oxidative scission of ethyl 2,2-dimethoxycyclopropane-1-carboxylates and methyl 2,2,6,6-tetramethoxybicyclo[2.2.0]hexane-1-carboxylates
  作者：M.Liliana Graziano、Maria Lasalvia、Vincenzo Piccialli、Donato Sica

  DOI：10.1016/0040-4039(95)02179-5

  日期：1996.1

  oxidative ring opening by regioselective scission of the electron-rich C1C2 bond for 1a-d, and both C1C2 and C1C6 bonds for 5a and 5b. Methyl ethyl oxobutanedioates 2a-d were obtained in the first case while the 3-substituted ethyl methyl 2-oxopentanedioates 6a and 6b in the second one. In the same reaction conditions, cyclopropanes substituted with electron withdrawing groups, namely cyclopropyl methyl

  在室温下，2,2-二甲氧基环丙烷-1-甲酸乙酯1a-d与2,2,6,6-四甲氧基双环[2.2.0]己烷-1-甲酸甲酯5a和5b与RuO 4在CCl 4中在室温下反应在两种情况下，都通过区域选择性断裂富电子的C1C2键的氧化开环为1a-d，而C1C2和C1C6键均为5a和5b。在第一种情况下获得了甲基乙基氧代丁二酸2a-d，而3-取代的乙基甲基2-氧代戊二酸6a和6b。在第二个。在相同的反应条件下，被吸电子基团取代的环丙烷，即环丙基甲基酮（3a）和环丙烷-1，1-二羧酸（3b）不反应。2,2-二甲氧基环丁烷-1-羧酸甲酯4也不具反应性。
• The relevance of ester exchange in oxalacetic esters to the decarbonmonoxylation reaction
  作者：Anthony L Fitzhugh、Richard S Strauss、Elizabeth N Brewer、Steven D Glassman、Maitland Jones

  DOI：10.1016/s0040-4039(00)98685-4

  日期：1985.1

  Oxalacetic esters undergo ester exchange at 120°C, at which temperature loss of CO does not occur. A new mechanism is proposed for the decarbonmonoxylation reaction.

  草酰乙酸酯在120°C进行酯交换，在此温度下不会发生CO的损失。提出了一种新的脱碳氨氧化反应机理。
• Evidence for ketene intermediates in the reactions of 2-oxobutanedioic acid diesters with alcohols and water
  作者：David W. Emerson、Richard L. Titus、Rowena M. Gonzalez

  DOI：10.1021/jo00298a037

  日期：1990.5
• Evidence for ketene intermediates in the decarbonylation of 2,4-dioxo acids and esters and 2-oxobutanedioic acid esters
  作者：David W. Emerson、Richard L. Titus、Rowena M. Gonzalez

  DOI：10.1021/jo00018a018

  日期：1991.8

  The mechanism by which alpha, gamma-dioxo carboxylic acid esters 1 and 2-oxobutanedioic acid diesters 2 lose CO was explored. The compounds, 5,5-dimethyl-2,4-dioxohexanoic acid ethyl ester, 1a, alpha,2-dioxocyclohexaneacetic acid ethyl ester, 1b, and alpha,1-dioxotetrahydro-2-naphthaleneacetic acid ethyl ester, 1c, lose CO at 170-190-degrees-C to yield the corresponding beta-keto esters 3a-c. When compounds 1 or the parent acids 4 were heated to 170-190-degrees-C with water in a sealed reactor, they yielded ketones resulting from replacement by H of C(O)CO2R from 1 or C(O)CO2H from 4. beta-Keto esters suffered replacement by H of the carbethoxy group to yield the corresponding ketones when heated with water at about 105-degrees-C. Acylketenes, such as 4,4-dimethyl-1-pentene-1,3-dione, 6a, 2-oxocyclohexylidenemethanone, 6b, 1-oxotetrahydro-2-naphthylidenemethanone, 6c, 3-methyl-1-butene-1,3-dione, 6d, and 1-butene-1,3-dione, 6e, are implicated as the common intermediates that react with water to form beta-keto acids that subsequently decarboxylate to yield the ketones 5. Intense IR frequencies in the region of 2120-2140 cm-1, characteristic of ketenes, are observed when 1,2, or 3 is subjected to GC-FTIR analysis with the injector and light pipe at 280-degrees-C. Loss of carbon monoxide and alcohol at high temperature is required to form 6 from 1, while only the loss of alcohol at lower temperature is needed to form 6 from 3.
• EMERSON, DAVID W.;TITUS, RICHARD L.;GONZALEZ, ROWENA M., J. ORG. CHEM., 55,(1990) N1, C. 3572-3576
  作者：EMERSON, DAVID W.、TITUS, RICHARD L.、GONZALEZ, ROWENA M.

  DOI：——

  日期：——