dimethyl 4,4-dicyanoheptanedioate | 151585-45-4

• 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: dimethyl 4,4-dicyanoheptanedioate
• 英文别名: Dimethyl 3,3-dicyanopimelate
• CAS: 151585-45-4
• 化学式: C₁₁H₁₄N₂O₄
• 分子量: 238.243
• InChiKey: RRHBVLQVSWOIOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  丙烯酸甲酯（MA） 、 丙二腈 在 poly(N-vinylimidazole) 作用下， 以 水 为溶剂， 反应 8.0h， 以90%的产率得到dimethyl 4,4-dicyanoheptanedioate
  参考文献：
  名称：

  聚（N-乙烯基咪唑）作为有效的可回收催化剂，用于 CH-酸与水中缺电子烯烃的迈克尔加成反应

  摘要：

  研究了聚（N-乙烯基咪唑）作为碱性可回收催化剂的效率，用于在环境温度下将 CH 酸与丙烯腈、丙烯酸甲酯、甲基乙烯基酮和甲基乙烯基砜在水中进行迈克尔加成。在这些反应中，可能形成 1:1 和 1:2 加合物。

  DOI：

  10.1007/s11172-011-0401-7

文献信息

• The remarkable catalytic activity of ultra-small free-CeO₂ nanoparticles in selective carbon–carbon bond formation reactions in water at room temperature
  作者：Subhash Banerjee

  DOI：10.1039/c5nj00500k

  日期：——

  A simple and efficient protocol for selective bis-Michael addition and mono-allylation of active methylene compounds has been demonstrated using ultra-small size (∼5 nm) uncapped cerium oxide nanoparticles (free-CeO₂ NPs) as a reusable catalyst in water at room temperature.

  使用直径约5纳米的未帽化氧化铈纳米颗粒（自由CeO₂ NPs）作为可重复使用的催化剂，在室温下在水中展示了一种用于选择性双Michael加成和单烯丙基化活性亚甲基化合物的简单高效协议。
• Remarkable catalytic activity of silica nanoparticle in the bis-Michael addition of active methylene compounds to conjugated alkenes
  作者：Subhash Banerjee、Swadeshmukul Santra

  DOI：10.1016/j.tetlet.2009.01.154

  日期：2009.5

  We have demonstrated the remarkable catalytic activity of silica nanoparticles (NPs) in the unusual bis-Michael addition of active methylene compounds to conjugated alkenes at room temperature. The catalyst silica NPs were reused up to seven runs without appreciable loss of catalytic activity.

  我们已经证明了在室温下，二氧化硅纳米颗粒（NPs）在活性亚甲基化合物向共轭烯烃的不寻常的双-迈克尔加成反应中具有非凡的催化活性。催化剂二氧化硅NP可重复使用多达7次，而催化活性没有明显损失。
• A simple, efficient and green procedure for Michael addition catalyzed by [C4dabco]OH ionic liquid
  作者：Sanjoy Keithellakpam、Warjeet S. Laitonjam

  DOI：10.1016/j.cclet.2014.01.032

  日期：2014.5

  liquid, 1-butyl-4-aza-1-azaniabicyclo[2.2.2]octane hydroxide, has been developed as a catalyst for a convenient and rapid method for the Michael addition of active methylene compounds to α , β -unsaturated carboxylic esters and nitriles. The method is very simple, and the yields are very high. The catalyst can be recycled several times without much loss of activity.

  摘要已开发出基于dabco的碱性离子液体1-丁基-4-氮杂-1-氮杂双环[2.2.2]辛烷氢氧化​​物，作为一种方便快捷的方法，用于将活性亚甲基化合物迈克尔加成的方法，β-不饱和羧酸酯和腈。该方法非常简单，并且产率很高。催化剂可以循环使用几次而不会损失很多活性。
• Cesium Carbonate Supported on Alumina for the Michael Addition of Diethyl Malonate to Methyl Acrylates
  作者：Tetsunari Hida、Kenichi Komura、Yoshihiro Sugi

  DOI：10.1246/bcsj.20110115

  日期：2011.9.15

  The cesium salts supported on γ-Al2O3 were highly active catalysts for the Michael addition of diethyl malonate (1) to methyl acrylate (2) in toluene as solvent. The use of a limited amount of 2 gave diethyl [2-(methoxycarbonyl)ethyl]malonate (3), however the formation of diethyl bis[2-(methoxycarbonyl)ethyl]malonate (4) was enhanced by the increase in amounts of 2. Catalytic activities were easily recovered by the calcination of used catalysts. IR and XRD observations indicate that the active catalytic species are Cs2CO3 on Al2O3. The use of malononitrile enhanced the formation of the diadduct as principal products by addition to methyl acrylate. Other methyl acrylates, such as methyl methacrylate and methyl crotonate, gave low yield of the products.

  负载在 γ-Al2O3 上的铯盐是在甲苯溶剂中丙二酸二乙酯 (1) 与丙烯酸甲酯 (2) 发生迈克尔加成反应的高活性催化剂。使用有限量的 2 得到[2-(甲氧基羰基)乙基]丙二酸二乙酯 (3)，然而，双[2-(甲氧基羰基)乙基]丙二酸二乙酯 (4) 的形成随着 2 用量的增加而增强。通过煅烧用过的催化剂很容易恢复催化活性。 IR 和 XRD 观察表明活性催化物质是 Al2O3 上的 Cs2CO3。通过与丙烯酸甲酯加成，丙二腈的使用增强了作为主要产物的二加合物的形成。其他丙烯酸甲酯，例如甲基丙烯酸甲酯和巴豆酸甲酯，产物收率较低。
• A simple and highly efficient procedure for construction of quaternary carbons centers by tributylphosphine catalyzed bis-Michael addition
  作者：Da-Zhen Xu、Ming-Zhe Zhan、You Huang

  DOI：10.1016/j.tet.2013.11.103

  日期：2014.1

  The tributylphosphine-catalyzed bis-Michael addition reaction of various kinds of a,13-unsaturated carbonyl compounds with active methylenes is described. This is a convenient and rapid method for generating quaternary carbons centers and useful procedure for the synthesis of branched core and highly substituted trans cyclohexanones. All the reactions were completed in 60 min and afford the corresponding products in excellent yields. (C) 2013 Elsevier Ltd. All rights reserved.