2-(1-methyl-3-phenylallyl)malonic acid dimethyl ester | 87802-86-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(1-methyl-3-phenylallyl)malonic acid dimethyl ester
• 英文别名: dimethyl 2-(4-phenylbut-3-en-2-yl)malonate；dimethyl (4-phenyl-3-buten-2-yl)malonate；Dimethyl 2-(4-phenylbut-3-en-2-yl)propanedioate
• CAS: 87802-86-6
• 化学式: C₁₅H₁₈O₄
• 分子量: 262.306
• InChiKey: FQUOZEVDJXQKDV-UHFFFAOYSA-N

物化性质

• 沸点：
  210 °C(Press: 34 Torr)
• 密度：
  1.105±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (phenyl-methyl-π-allyl)dicarbonylnitrosyl iron 、 丙二酸二甲酯 在 lithium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以62%的产率得到2-(1-methyl-3-phenylallyl)malonic acid dimethyl ester
  参考文献：
  名称：

  Reactivity of (η3-allyl)dicarbonylnitrosyl iron complexes with dimethyl malonate and diisobutyl malonate

  摘要：

  在本文中，我们描述了我们之前报道的（η3-烯丙基）二羰基亚硝基铁配合物（1–9）的反应性。在此背景下，进行了1–9与二甲基马来酸酯和二异丁基马来酸酯的化学计量反应。通过气相色谱分析反应混合物，确定了所得到的产物（10–25）的区域选择性。这些产物通过柱色谱纯化，然后通过红外光谱、1H NMR、13C NMR光谱和质谱进行结构表征。也研究了不同配体L（L = CO, PPh3, SIMES (1,3-二-tert-丁基咪唑氟磷酸盐), BUSI（1,3-双（2,4,6-三甲基苯）-4,5-二氢-3H-咪唑-1-氟磷酸盐））及其对取代模式的影响。引入可变取代基表现出多样的反应性。一般观察到，通过增大取代基的大小，(η3-烯丙基)二羰基亚硝基铁配合物（1–9）的反应性降低。由于烯丙基部分的取代模式，对反应性产生了明显的影响。从C-3位置移位到C-2位置时，转化率从81%显著降低至68%。

  DOI：

  10.4314/bcse.v31i2.11

文献信息

• Asymmetric allylic substitutions on symmetrical and non-symmetrical substrates using [5]ferrocenophane ligands
  作者：Radovan Šebesta、Andrea Škvorcová、Branislav Horváth

  DOI：10.1016/j.tetasy.2010.05.054

  日期：2010.8

  A series of [5]ferrocenophane diphosphane ligands were used in Pd-catalyzed allylic substitution reactions. With a symmetrical substrate, 1,3-diphenylpropenyl acetate, enantioselectivities between 70% and 94% ee were observed. Several non-symmetrically substituted allylic substrates were also used. Depending on the substituents of the non-symmetrical allylic substrates, various degrees of regioselectivity (from 1:1 to 100:0) and enantioselectivity (from 0% to 96% ee) were observed. Tentative catalytically active complexes were studied by DFT computational methods. (C) 2010 Elsevier Ltd. All rights reserved.
• Influence of structural changes in ferrocene phosphane aminophosphane ligands on their catalytic activity
  作者：Radovan Šebesta、Andrea Škvorcová

  DOI：10.1016/j.jorganchem.2009.01.027

  日期：2009.5

  New phosphane aminophosphane ligands based on [3]ferrocenophane skeleton were synthesized using a direct double lithiation followed by phosphanylation. Influence of ligand structure on catalytic performance was evaluated by performing a series of Pd-catalyzed allylic substitution on different substrates. Enantioselectivities up to 55% ee were obtained with bridged ligand compared to 33% ee with analogous non-bridged BoPhoz ligand. (C) 2009 Elsevier B.V. All rights reserved.