4-ethyl-1-methyl 2-methylsuccinate | 82701-20-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-ethyl-1-methyl 2-methylsuccinate
• 英文别名: ethyl 3-methoxycarbonylbutyrate；ethyl methyl methylbutanedioate；methyl 3-ethoxycarbonyl-2-methylpropanoate；methylsuccinic acid ethyl methyl ester；4-O-ethyl 1-O-methyl 2-methylbutanedioate
• CAS: 82701-20-0
• 化学式: C₈H₁₄O₄
• 分子量: 174.197
• InChiKey: AJFVBKSDOWPODB-UHFFFAOYSA-N

物化性质

• 沸点：
  204.4±8.0 °C(Predicted)
• 密度：
  1.037±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-ethyl-1-methyl 2-methylsuccinate 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 作用下， 以 四氯化碳 为溶剂， 以67%的产率得到4-ethyl-1-methyl 2-bromo-2-methylsuccinate
  参考文献：
  名称：

  Mechanism of electron impact ionization-induced halogen elimination from 2-methyl-2-bromosuccinates

  摘要：

  AbstractThe electron impact‐induced halogen elimination from 2‐methyl‐2‐bromosuccinates occurs only in the one of the two isomeric methyl ethyl esters in which the ethoxycarbonyl group is remote from the halogen, in analogy with the corresponding previously reported halosuccinates. However, the occurrence of debromination in dimethyl 2‐methyl‐2‐bromosuccinate contrasts with the behaviour of dimethyl bromosuccinate, indicating different mechanisms for this process in the two systems. Collision‐induced dissociation (CID) and deuterium labelling studies led to the conclusion that a hydrogen transfer from the 2‐methyl group to a carbonyl precedes the elimination of Br˙ from dimethyl 2‐methyl‐2‐bromosuccinate, resulting in a protonated dimethyl itaconate structure for the [M – Br]+ ion. An analogous process is the major route leading to [M – Br]+ ion from 1‐methyl‐4‐ethyl 2‐methyl‐2‐bromosuccinate. In this case deuterium labelling and CID measurements indicated a significant contribution of methyl ethyl citraconate and possibly mesaconate owing to partial operation of a mechanism similar to that reported for 1‐methyl‐4‐ethyl 2‐bromosuccinate.

  DOI：

  10.1002/oms.1210280315
• 作为产物：
  描述：

  methyl 3-carbamoylisobutyrate 生成 4-ethyl-1-methyl 2-methylsuccinate
  参考文献：
  名称：

  Process for producing 3-methyltetrahydrofuran

  摘要：

  一种生产3-甲基四氢呋喃的方法，其中在第一步中，将氢氰酸与甲基丙烯酸甲酯反应，产生3-氰基异丁酸甲酯。然后将3-氰基异丁酸甲酯与水和硫酸反应，产生一个产物，该产物与C.sub.1-C.sub.8脂肪醇反应，产生甲基琥珀酸酯。甲基琥珀酸酯经催化氢化制备3-甲基四氢呋喃。或者，将3-氰基异丁酸甲酯水合产生3-氨基基异丁酸甲酯，然后将其与甲酸酯反应形成甲基琥珀酸酯和甲酰胺，所得的甲基琥珀酸酯经催化氢化。该方法从廉价反应物中高选择性地和商业上有利地生产3-甲基四氢呋喃。3-甲基四氢呋喃可用作制备聚醚醇的常见材料，该聚醚醇用作制备氨纶纤维的起始原材料。

  公开号：

  US05618953A1

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。
• Graziano, M. L.; Cimminiello, Guido, Journal of Chemical Research, Miniprint, 1989, # 2, p. 446 - 457
  作者：Graziano, M. L.、Cimminiello, Guido

  DOI：——

  日期：——
• GRAZIANO, M. LILIANA;CIMMINIELLO, GUIDO
  作者：GRAZIANO, M. LILIANA、CIMMINIELLO, GUIDO

  DOI：——

  日期：——
• GRAZIANO, M. L.;SCARPATI, R., J. CHEM. SOC. PERKIN TRANS., 1985, N 2, 289-294
  作者：GRAZIANO, M. L.、SCARPATI, R.

  DOI：——

  日期：——
• Graziano, M. Liliana; Iesce, M. Rosaria; Cermola, Flavio, Journal of Chemical Research, Miniprint, 1992, # 1, p. 157 - 172
  作者：Graziano, M. Liliana、Iesce, M. Rosaria、Cermola, Flavio、Cimminiello, Guido

  DOI：——

  日期：——