2-(3-methyl-butoxymethylene)-malonic acid diethyl ester | 188760-99-8

• 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: 2-(3-methyl-butoxymethylene)-malonic acid diethyl ester
• 英文别名: diethyl 2-(3-methylbutoxymethylidene)propanedioate
• CAS: 188760-99-8
• 化学式: C₁₃H₂₂O₅
• 分子量: 258.315
• InChiKey: XHACXEPOHGPWLM-UHFFFAOYSA-N

物化性质

• 沸点：
  308.5±32.0 °C(Predicted)
• 密度：
  1.032±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.06
• 重原子数：
  18.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-(3-methyl-butoxymethylene)-malonic acid diethyl ester 在 lithium aluminium tetrahydride 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 2-[Bis(3-methylbutoxy)methyl]propane-1,3-diol
  参考文献：
  名称：

  Synthesis and lipase-catalyzed asymmetric acetylation of 3-hydroxy-2-hydroxymethylpropanal acetals

  摘要：

  Prochiral dialkylacetal derivatives of 3-hydroxy-2-hydroxymethylpropanal 6a-e were synthesized from the corresponding 2-substituted diethyl malonates 5a-e and subjected to asymmetric enzymatic acetylation. The diethyl malonates 5a-f were prepared from diethyl chloromethylenemalonate 3 by using either a one- or a two-step process. Asymmetric acetylation of 3-hydroxy-2-hydroxymethylpropanal diethyl acetal 6b with several enzymes was studied first, showing the highest enantiotopic selectivity with lipase from Pseudomonas fluorescens (PfL). Solvent effect was also investigated: the best selectivity was obtained in a mixture of hexane and diethyl ether. Furthermore, several other acetals 6a-e were also tested under the optimal acetylation conditions. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00018-9
• 作为产物：
  描述：

  diethyl (hydroxymethylene)malonate 在 吡啶 、 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 甲苯 为溶剂， 反应 0.25h， 生成 2-(3-methyl-butoxymethylene)-malonic acid diethyl ester
  参考文献：
  名称：

  Synthesis and lipase-catalyzed asymmetric acetylation of 3-hydroxy-2-hydroxymethylpropanal acetals

  摘要：

  Prochiral dialkylacetal derivatives of 3-hydroxy-2-hydroxymethylpropanal 6a-e were synthesized from the corresponding 2-substituted diethyl malonates 5a-e and subjected to asymmetric enzymatic acetylation. The diethyl malonates 5a-f were prepared from diethyl chloromethylenemalonate 3 by using either a one- or a two-step process. Asymmetric acetylation of 3-hydroxy-2-hydroxymethylpropanal diethyl acetal 6b with several enzymes was studied first, showing the highest enantiotopic selectivity with lipase from Pseudomonas fluorescens (PfL). Solvent effect was also investigated: the best selectivity was obtained in a mixture of hexane and diethyl ether. Furthermore, several other acetals 6a-e were also tested under the optimal acetylation conditions. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00018-9

文献信息

• Solvent‐Free Microwave Michael Addition Between EMME and Various Nucleophiles
  作者：André Loupy、Suk Jin Song、Seong Jin Cho、Dong Kyu Park、Tae Woo Kwon

  DOI：10.1081/scc-200046503

  日期：2005.1.1

  Michael addition reaction between EMME and various O, S, N nucleophiles were investigated in the presence of catalysts such as KF, KOH, or K(OCCH3)(3) under solvent-free conditions either neat or on alumina as solid support. Compared to low reactivity of alcohols (40 to 80% yields according to aliphatic chain), aniline or thiophenol. gave good to excellent yields (90-99%).