3,3-diethyl 1,5-dimethyl pentane-1,3,3,5-tetracarboxylate | 113203-28-4

• 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: 3,3-diethyl 1,5-dimethyl pentane-1,3,3,5-tetracarboxylate
• 英文别名: 3,3-diethyl-1,5-dimethylpentane-1,3,3,5-tetracarboxylate；diethyl bis[2-(methoxycarbonyl)ethyl]malonate；pentane-1,3,3,5-tetracarboxylic acid-3,3-diethyl ester-1,5-dimethyl ester；Pentan-1,3,3,5-tetracarbonsaeure-3,3-diaethylester-1,5-dimethylester；1,3,3,5-Pentanetetracarboxylic acid, 3,3-diethyl 1,5-dimethyl ester；3-O,3-O-diethyl 1-O,5-O-dimethyl pentane-1,3,3,5-tetracarboxylate
• CAS: 113203-28-4
• 化学式: C₁₅H₂₄O₈
• 分子量: 332.351
• InChiKey: NQXPUCNKHCSPRK-UHFFFAOYSA-N

物化性质

• 熔点：
  52-54 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  180-190 °C(Press: 1 Torr)
• 密度：
  1.145±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  23
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  3,3-diethyl 1,5-dimethyl pentane-1,3,3,5-tetracarboxylate 在 水 、 sodium chloride 作用下， 以 二甲基亚砜 为溶剂， 反应 5.5h， 以77%的产率得到4-Ethoxycarbonyl-heptanedioic acid dimethyl ester
  参考文献：
  名称：

  Synthesis of polyfunctional aliphatic carbonyl compounds under phase-transfer conditions

  摘要：

  We have studied mono- and dialkylation of malonic, acetoacetic, and cyanoacetic esters with esters of haloacetic and beta-halopropionic acids and addition of the CH acids mentioned and their analogs to methyl and ethyl acrylate under phase-transfer catalysis conditions, and also deethoxycarbonylation of the obtained products. We have demonstrated for the first time the possibility of Dieckmann cyclization under phase-transfer catalysis conditions and have developed a simple method for the synthesis of 2,3-di(ethoxycarbonyl)cyclopentanone, a key intermediate in the syntheis of deoxyprostaglandins, by cyclization of triethyl 1,2,4-butanetricarboxylate.

  DOI：

  10.1007/bf00961357
• 作为产物：
  描述：

  丙二酸二乙酯 在 苄基三乙基氯化铵 氢氧化钾 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3,3-diethyl 1,5-dimethyl pentane-1,3,3,5-tetracarboxylate
  参考文献：
  名称：

  Synthesis of polyfunctional aliphatic carbonyl compounds under phase-transfer conditions

  摘要：

  We have studied mono- and dialkylation of malonic, acetoacetic, and cyanoacetic esters with esters of haloacetic and beta-halopropionic acids and addition of the CH acids mentioned and their analogs to methyl and ethyl acrylate under phase-transfer catalysis conditions, and also deethoxycarbonylation of the obtained products. We have demonstrated for the first time the possibility of Dieckmann cyclization under phase-transfer catalysis conditions and have developed a simple method for the synthesis of 2,3-di(ethoxycarbonyl)cyclopentanone, a key intermediate in the syntheis of deoxyprostaglandins, by cyclization of triethyl 1,2,4-butanetricarboxylate.

  DOI：

  10.1007/bf00961357

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。
• Merrifield Resin−C₆H₄CH₂N₃P(MeNCH₂CH₂)₃N:  An Efficient Reusable Catalyst for Room-Temperature 1,4-Addition Reactions and a More Convenient Synthesis of Its Precursor P(MeNCH₂CH₂)₃N
  作者：Reddy、John G. Verkade

  DOI：10.1021/jo062505z

  日期：2007.4.1

  donors were efficiently catalyzed at room temperature by the title reusable Merrifield resin-supported catalyst. Advantages of this catalyst include a simple workup (filtration of the reaction mixture) and good to excellent product yields. We also report a substantially simplified synthesis of the commercially available strong nonionic base 1, a precursor to the title polymer-bound catalyst.

  室温下，标题为可重复使用的Merrifield树脂负载的催化剂可有效地催化1,4-加成物中具有多种供体的多种Michael受体。该催化剂的优点包括简单的后处理（反应混合物的过滤）和良好至极好的产物产率。我们还报告了商业上可获得的强非离子碱1的大幅简化合成，该碱是标题聚合物结合的催化剂的前体。
• 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。
• Utilisation de membranes echangeuses d'ions en electrosynthese organique.
  作者：Eugène Raoult、Jean Sarrazin、André Tallec

  DOI：10.1016/s0040-4020(01)87706-1

  日期：1987.1

  per mole. Putting to the test donors with decreasing acidity (2-nitropropane, malononitrile, diethyl malonate, ethyl cyanacetate, 2-methylcyclohexanone, fluorene) allows to estimate the basicity level that can be reached at such an interface. The influence of different factors (such as the nature of the ion exchange membrane, the basicity of the second side of the membrane, the presence of a probase)

  可以通过在多孔阴极和固体聚合物电解质之间的界面上在不存在支持电解质的情况下在质子惰性介质中电生成的碱来引发向丙烯腈或酰化甲酯中的碳酸的添加。电力消耗低于每摩尔法拉第10 -2法拉第。将酸度降低的供体（2-硝基丙烷，丙二腈，丙二酸二乙酯，氰基乙酸乙酯，2-甲基环己酮，芴）置于酸性下，可以估算在这种界面上可以达到的碱性水平。研究了不同因素（例如离子交换膜的性质，膜第二面的碱性，碱的存在）对反应速率和产率的影响。
• 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。