cyclopropane-1,2-dicarboxylic acid 2-ethyl ester 1-methyl ester | 13950-18-0

• 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: cyclopropane-1,2-dicarboxylic acid 2-ethyl ester 1-methyl ester
• 英文别名: 2-ethyl 1-methyl (1R,2S)-1-methylcyclopropane-1,2-dicarboxylate；2-ethyl 1-methyl 1-methylcyclopropane-1,2-dicarboxylate；2-O-ethyl 1-O-methyl (1R,2S)-1-methylcyclopropane-1,2-dicarboxylate
• CAS: 13950-18-0
• 化学式: C₉H₁₄O₄
• 分子量: 186.208
• InChiKey: VVVZDNYVRXTCNZ-HZGVNTEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.75
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  甲基丙烯酸甲酯 、 二氯乙酸乙酯 在 Cp*RuCl2PPh3 、 magnesium 作用下， 以 甲苯 、 四氢呋喃 为溶剂， 反应 11.0h， 生成 cyclopropane-1,2-dicarboxylic acid 2-ethyl ester 1-methyl ester 、 cyclopropane-1,2-dicarboxylic acid 2-ethyl ester 1-methyl ester
  参考文献：
  名称：

  在钌催化剂存在下，通过顺序原子转移自由基加成和脱氯进行烯烃环丙烷化

  摘要：

  在没有重氮的情况下：在钌催化剂和镁的存在下，烯烃与二氯化合物的还原偶联以良好的收率得到环丙烷（参见方案）。

  DOI：

  10.1002/anie.200904278

文献信息

• Stereoselective Cyclopropanation Under Solvent Free Conditions: Catalyzed by a Green and Efficient Recyclable Cu-Exchanged Bentonite
  作者：Choukry K. Bendeddouche、Mehdi Adjdir、Hadj Benhaoua

  DOI：10.2174/1570178613666160109005049

  日期：2016.2.10

  of carbene generated from ethyl diazoacetate in the presence of a greener Cu-exchanged bentonite catalyst to olefin under solvent free condition. The cyclopropanes were obtained with good yields. Our own contribution in this area was to introduce a modified Algerian bentonite as a catalyst and microwave activation as a mode of heating. Methods: A catalytic material developed from natural type montmorillonite

  背景：在无溶剂条件下，通过在较绿色的铜交换膨润土催化剂存在下，将重氮乙酸乙酯产生的卡宾加入烯烃中，对环丙烷化反应进行了检查。以良好的产率获得环丙烷。我们在这一领域的贡献是引入了改性的阿尔及利亚膨润土作为催化剂，并引入了微波活化作为加热方式。 方法：采用不同的光谱方法表征了由天然类型的蒙脱土粘土，氧化镁（西部阿尔及利亚）矿床中的阳离子交换（Cu2 +）形成的催化材料。在微波辐射下烯烃的环丙烷化反应中探索了该新材料的催化性能。以铜交换膨润土为催化剂，进行了微波活化与经典加热之间的比较研究。 结果：在微波辐射下，Cu2 +交换的粘土是重氮化合物生成卡宾的有效催化剂。在无溶剂条件下以中等非对映选择性进行羧酸环丙烷的形成。收率良好，催化剂可以重复使用至少三遍，而催化活性没有明显损失。 结论：这项工作表明，偶联的“改性粘土/微波活化”是一种清洁，简单地获得官能化环丙烷的方法。这种可重复使用的铜交换粘土
• Bendeddouche, Kamel C.; Rechsteiner, Benno; Texier-Boullet, Francoise, Journal of Chemical Research - Part S, 2002, # 3, p. 114 - 117
  作者：Bendeddouche, Kamel C.、Rechsteiner, Benno、Texier-Boullet, Francoise、Hamelin, Jack、Benhaoua, Hadj

  DOI：——

  日期：——
• Recyclable Polymer- and Silica-Supported Ruthenium(II)-Salen Bis-pyridine Catalysts for the Asymmetric Cyclopropanation of Olefins
  作者：Christopher S. Gill、Krishnan Venkatasubbaiah、Christopher W. Jones

  DOI：10.1002/adsc.200800779

  日期：2009.6

  Abstractmagnified imageHomogeneous ruthenium(II)‐salen bis‐pyridine complexes are known to be highly active and selective catalysts for the asymmetric cyclopropanation of terminal olefins. Here, new methods of heterogenization of these Ru‐salen catalysts on polymer and porous silica supports are demonstrated for the facile recovery and recycle of these expensive catalysts. Activities, selectivities, and recyclabilities are investigated and compared to the analogous homogeneous and other supported catalysts for asymmetric cyclopropanation reactions. The catalysts are characterized with a variety of methods including solid state cross‐polarization magic‐angle spinning (CP MAS) 13C and 29Si NMR, FT‐IR, elemental analysis, and thermogravimetric analysis. Initial investigations produced catalysts possessing high selectivities but decreasing activities upon reuse. Addition of excess pyridine during the washing steps between cycles was observed to maintain high catalytic activities over multiple cycles with no impact on selectivity. Polymer‐supported catalysts showed superior activity and selectivity compared to the porous silica‐supported catalyst. Additionally, a longer, flexible linker between the Ru‐salen catalyst and support was observed to increase enantioselectivity and diastereoselectivity, but had no effect on activity of the resin catalysts. Furthermore, the polymer‐supported Ru‐salen‐Py2 catalysts were found to generate superior selectivities and yields compared to other leading heterogeneous asymmetric cyclopropanation catalysts.
• PAZYNINA, G. V.;LUKYANETS, E. A.;BOLESOV, I. G.
  作者：PAZYNINA, G. V.、LUKYANETS, E. A.、BOLESOV, I. G.

  DOI：——

  日期：——