tetramethyl 2-methylpropane-1,1,3,3-tetracarboxylate | 117614-33-2

• 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: tetramethyl 2-methylpropane-1,1,3,3-tetracarboxylate
• 英文别名: Tetramethyl 2-methyl-1,1,3,3-propanetetracarboxylate
• CAS: 117614-33-2
• 化学式: C₁₂H₁₈O₈
• 分子量: 290.27
• InChiKey: HBESQLIEUULRDL-UHFFFAOYSA-N

物化性质

• 沸点：
  307.0±37.0 °C(Predicted)
• 密度：
  1.201±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tetramethyl 2-methylpropane-1,1,3,3-tetracarboxylate 在 sodium iodide 作用下， 以 甲醇 为溶剂， 以95%的产率得到Tetramethyl ester of 3-methylcyclopropane-1,1,2,2,-tetracarboxylic acid
  参考文献：
  名称：

  Electrochemical cyclization of tetramethyl esters of 2-substituted propane-1,1,3,3-tetracarboxylic acids in the presence of salts of hydrohalic acids

  摘要：

  The chemical and electrochemical cyclization of tetramethyl esters of 2-substituted propane-1,1,3,3-tetracarboxylic acids in the presence of hydrohalic acid salt mediators were studied. It was found that the chemical variant of the cyclization of the corresponding alpha,alpha'-dianions of esters of propane-1,1,3,3-tetracarboxylic acids by the action of iodine or bromine is substantially inferior to the electrochemical variant. In the latter case, the esters of substituted cyclopropane-1,1,2,2-tetracarboxylic acids are formed in a 87-98% yield. The tetramethyl ester of 2-isopropylpropane-1,1,3,3-tetracarboxylic acid, which under the electrolysis conditions decomposes according to a Michael retroreaction is an exception.

  DOI：

  10.1007/bf01184531
• 作为产物：
  描述：

  三乙胺 、 丙二酸二甲酯 在 叔丁基过氧化氢 、 diiron nonacarbonyl 作用下， 以 癸烷 为溶剂， 反应 0.17h， 以30%的产率得到tetramethyl 2-methylpropane-1,1,3,3-tetracarboxylate
  参考文献：
  名称：

  Iron-Catalyzed Oxidation of Tertiary Amines: Synthesis of β-1,3-Dicarbonyl Aldehydes by Three-Component C–C Couplings

  摘要：

  beta-1,3-Dicarbonyl aldehydes were synthesized by iron-catalyzed oxidative reactions between 1,3-dicarbonyl compounds and two molecules of tertiary amines in the presence of tert-butyl hydroperoxide (TBHP). alpha,beta-Unsaturated aldehydes generated by tertiary amine oxidation In situ act as key intermediates under mild reaction conditions.

  DOI：

  10.1021/ol202749x

文献信息

• A Simple and Direct Access to Ethylidene Malonates
  作者：Françoise Dumas、Maité Sylla、Delphine Joseph、Emilie Chevallier、Cheikhou Camara

  DOI：10.1055/s-2006-926344

  日期：——

  The condensation of active methylene compounds 1 with acetaldehyde was efficiently promoted by a catalytic amount of lithium bromide in the presence of acetic anhydride to give ethylidene malonates 2 in 77-97% yield.

  在乙酸酐存在下，催化量的溴化锂有效地促进了活性亚甲基化合物 1 与乙醛的缩合，得到亚乙基丙二酸盐 2，收率为 77-97%。
• Conjugate intra- and intermolecular addition mediated by methoxide anion on polymeric support
  作者：Cristiana Fava、Roberta Galeazzi、Eugenia Maria Gonzalez-Rosende、Mario Orena

  DOI：10.1016/s0040-4039(00)01490-8

  日期：2000.10

  By treatment with methoxide anion on polymeric support (IRA 900), chiral beta -oxo or beta -sulphonylamides 2 bearing an alpha,beta -unsaturated ester gave 3,4-disubstituted pyrrolidin-2-ones 3 as easily separable diastereomeric mixtures in good yield and moderate-to-good stereoselection. The polymeric reagent was also effective in promoting both intermolecular conjugate addition and alkylation reactions. (C) 2000 Published by Elsevier Science Ltd.
• EHLINSON, M. N.;FEDUKOVICH, S. K.;NIKISHIN, G. I., IZV. AN CCCP. CEP. XIM.,(1990) N2, S. 2783-2789
  作者：EHLINSON, M. N.、FEDUKOVICH, S. K.、NIKISHIN, G. I.

  DOI：——

  日期：——
• Electrochemical cyclization of tetramethyl esters of 2-substituted propane-1,1,3,3-tetracarboxylic acids in the presence of salts of hydrohalic acids
  作者：M. N. Elinson、S. K. Fedukovich、G. I. Nikishin

  DOI：10.1007/bf01184531

  日期：1990.12

  The chemical and electrochemical cyclization of tetramethyl esters of 2-substituted propane-1,1,3,3-tetracarboxylic acids in the presence of hydrohalic acid salt mediators were studied. It was found that the chemical variant of the cyclization of the corresponding alpha,alpha'-dianions of esters of propane-1,1,3,3-tetracarboxylic acids by the action of iodine or bromine is substantially inferior to the electrochemical variant. In the latter case, the esters of substituted cyclopropane-1,1,2,2-tetracarboxylic acids are formed in a 87-98% yield. The tetramethyl ester of 2-isopropylpropane-1,1,3,3-tetracarboxylic acid, which under the electrolysis conditions decomposes according to a Michael retroreaction is an exception.
• Iron-Catalyzed Oxidation of Tertiary Amines: Synthesis of β-1,3-Dicarbonyl Aldehydes by Three-Component C–C Couplings
  作者：Weiping Liu、Jinhua Liu、Daisuke Ogawa、Yasushi Nishihara、Xingwei Guo、Zhiping Li

  DOI：10.1021/ol202749x

  日期：2011.12.2

  beta-1,3-Dicarbonyl aldehydes were synthesized by iron-catalyzed oxidative reactions between 1,3-dicarbonyl compounds and two molecules of tertiary amines in the presence of tert-butyl hydroperoxide (TBHP). alpha,beta-Unsaturated aldehydes generated by tertiary amine oxidation In situ act as key intermediates under mild reaction conditions.