methyl 4-cyano-2,2-dimethylbutanoate | 132282-38-3

• 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: methyl 4-cyano-2,2-dimethylbutanoate
• 英文别名: Cyano-4-dimethyl-2,2-buttersaeuremethylester
• CAS: 132282-38-3
• 化学式: C₈H₁₃NO₂
• 分子量: 155.197
• InChiKey: WTNZOELZCRICBO-UHFFFAOYSA-N

物化性质

• 沸点：
  241.0±23.0 °C(Predicted)
• 密度：
  0.985±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.49
• 重原子数：
  11.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  50.09
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  1-甲氧基-1-(三甲基甲硅氧基)-2-甲基-1-丙烯 在 四丁基氟化铵 、 zinc dibromide 作用下， 以 四氯化碳 为溶剂， 反应 18.0h， 生成 methyl 4-cyano-2,2-dimethylbutanoate
  参考文献：
  名称：

  Quendo, A.; Rousseau, G., Synthetic Communications, 1989, vol. 19, # 9-10, p. 1551 - 1560

  摘要：

  DOI：

文献信息

• Reaction of Ketene Silyl Acetals with Unsaturated Nitrites in the Presence of Titanium Tetrachloride
  作者：Syed Masarrat Ali、Gérard Rousseau

  DOI：10.1016/s0040-4020(01)87886-8

  日期：1990.1

  The reaction of ketene alkyl silyl acetals with acrylonitrile in the presence of titanium tetrachloride in dichloromethane at -80°C leads to coupled compounds. Formation of these products can be explained by the transformation of ketene acetals into enoxy radicals trapping of these radicals by acrylonitrile and then dimerization. With bisketene acetals derived from glutarate and pimelate a ring closure

  乙烯酮烷基甲硅烷基缩醛与丙烯腈在四氯化钛存在下于二氯甲烷中于-80°C反应生成偶合化合物。这些产物的形成可以通过将乙烯酮缩醛转化为被丙烯腈俘获这些自由基然后二聚化的环氧自由基来解释。使用由戊二酸酯和庚二酸酯衍生的双烯酮缩醛，观察到闭环反应，导致形成环戊烷和环壬烷衍生物。衍生自高级二酯的乙烯酮缩醛未观察到环化。
• Synthetic applications of the [2+2] cycloaddition products of ketene alkylsilylacetals with acrylonitrile
  作者：Gérard Rousseau、Alain Quendo

  DOI：10.1016/s0040-4020(01)88226-0

  日期：1992.1

  2-Cyanocyclobutane alkylsilylacetals, obtained by a [2+2] cycloaddition reaction of ketene alkylsilylacetals and acrylonitrile, have allowed the synthesis of 2-cyanoclobutanones, 4-chloro-4-cyanobutanoates and 4-cyanobutanoates by respectively acidic catalysis, FeCl3 cleavage and nBu4NF treatment. The cycloadducts obtained from chloroketene alkylsilylacetals give 2-cyanocyclopropanecarboxylates by

  通过乙烯酮烷基甲硅烷基乙缩醛和丙烯腈的[2 + 2]环加成反应获得的2-氰基环丁烷烷基甲硅烷基缩醛可以分别通过酸性催化，FeCl 3裂解和二价合成2-氰基丁烷酮，4-氯-4-氰基丁酸酯和4-氰基丁酸酯。nBu 4 NF处理。由氯乙烯烯烷基甲硅烷基缩醛得到的环加合物通过与nBu 4 NF反应而得到2-氰基环丙烷羧酸酯。
• Cage Like Al-KIT-5 Mesoporous Materials for C–C Bond Formation Reactions Under Solvent Free Conditions
  作者：Pranjal K. Baruah、Prantu Dutta、Pranjal Kalita

  DOI：10.1007/s10562-015-1611-7

  日期：2015.12

  condition. Mukaiyama-aldol and Mukaiyama–Michael reactions of silyl ketene acetal with aldehyde and α, β-unsaturated carbonyl compounds produced β-hydroxy esters and 1, 5-dicarbonyl compounds, respectively in good yields. The product selectivity was found to be 100 % in a short reaction period. The high acidity, 3D pores, and a huge space in the nano-cages materials make them attractive candidate for carrying

  摘要 C-C 键形成反应在化学中具有重要意义。因此，化学家对开发 C-C 键形成的新方法越来越感兴趣。我们在这里报告了三维纳米笼介孔铝硅酸盐材料 Al-KIT-5，它在无溶剂条件下对向山-羟醛和向山-迈克尔反应表现出非常好的催化活性。甲硅烷基乙烯酮缩醛与醛和 α, β-不饱和羰基化合物的 Mukaiyama-aldol 和 Mukaiyama-Michael 反应分别以良好的产率产生了 β-羟基酯和 1, 5-二羰基化合物。发现在较短的反应时间内产物选择性为 100%。纳米笼材料的高酸度、3D 孔和巨大的空间使它们成为进行重要有机反应的有吸引力的候选者。
• ——
  作者：Torsten Zytowski、Bernhard Knühl、Hanns Fischer

  DOI：10.1002/(sici)1522-2675(20000315)83:3<658::aid-hlca658>3.0.co;2-z

  日期：2000.3.15

  Absolute rate constants and some of their Arrhenius parameters were obtained by time-resolved electron spin resonance (ESR) spectroscopy for the addition of the 2-(alkoxycarbonyl)propan-2-yl and 3,3,3-trifluoroacetonyl (= 3,3,3-trifluoro-2-oxopropyl) radicals to a variety of mono- and 1,1-disubstituted alkenes. Their analysis shows that the addition of 2-(alkoxycarbonyl)propan-2-yl is mainly governed by the exothermicity of the reaction with slight modifications by nucleophilic and electrophilic effects giving rise to an overall ambiphilic behavior. In contrast, large electrophilic polar effects dominate the addition of the 3,3,3-trifluoroacetonyl (= 3,3,3-frifluoro-2-oxopropan-2-yl) radical, as it is expected from its large electron affinity. For both radicals, the activation energies are well-predicted by analytic equations for the enthalpic and polar terms. A comparison of the rate data of 2-(alkoxycarbonyl)propan-2-yl with the homo- and copolymerization rate constants of the propagating radical of methyl methacrylate shows that the additions of these structurally related low- and high-molecular-weight radicals to alkenes are governed by very similar effects.
• Cauquis,G.; Haemmerle,B., Bulletin de la Societe Chimique de France, 1970, p. 190 - 192
  作者：Cauquis,G.、Haemmerle,B.

  DOI：——

  日期：——