(S)-diethyl 2-(1-(2-methoxyphenyl)-3-oxo-3-phenylpropyl)malonate | 1608116-79-5

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: (S)-diethyl 2-(1-(2-methoxyphenyl)-3-oxo-3-phenylpropyl)malonate
• CAS: 1608116-79-5
• 化学式: C₂₃H₂₆O₆
• 分子量: 398.456
• InChiKey: RHRDLTXSLNALRS-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.79
• 重原子数：
  29.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  78.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  2-methoxychalcone 、 丙二酸二乙酯 在 1-((S)-2-hydroxy-1-phenylethyl)-3-((R)-(6-methoxyquinolin-4-yl)((1S,2R,4S,5R)-5-vinylquinuclidin-2-yl)methyl)thiourea 、 sodium hydroxide 作用下， 以 氯仿 为溶剂， 反应 10.0h， 以99%的产率得到(S)-diethyl 2-(1-(2-methoxyphenyl)-3-oxo-3-phenylpropyl)malonate
  参考文献：
  名称：

  金鸡纳生物碱衍生的双官能叔胺-硫脲带有多个氢键供体， 催化丙二酸对苯二酚的高度对映选择性迈克尔加成反应†

  摘要：

  查耳酮仍然是迈克尔反应中的挑战底物，仅取得了有限的成功。这项工作描述了由金鸡纳生物碱衍生的双官能叔胺-硫脲携带多个氢键供体催化的丙二酸二乙酯与查耳酮的高度对映选择性迈克尔加成反应。

  DOI：

  10.1039/c4ob00203b

文献信息

• Crown ether derived from d-glucose as an efficient phase-transfer catalyst for the enantioselective Michael addition of malonates to enones
  作者：Zsolt Rapi、Alajos Grün、Tamás Nemcsok、Dóra Hessz、Mihály Kállay、Miklós Kubinyi、György Keglevich、Péter Bakó

  DOI：10.1016/j.tetasy.2016.08.010

  日期：2016.10

  A monoaza-15-crown-5 lariat ether derived from D-glucose 1 has been applied as a chiral phase-transfer catalyst in the Michael addition of diethyl, dimethyl, diisopropyl and dibenzyl malonates to enones under mild conditions to afford the adducts with good to excellent enantioselectivities. In the reaction of diethyl malonate with substituted trans-chalcone, the adducts with in enantioselectivities up to 89% ee. Among the reactions of substituted diethyl malonates, those of diethyl acetoxymalonate gave the best results (96% ee). The effect of the substituents of the chalcone was also investigated in reactions with diethyl acetoxymalonate. Among the chalcones substituted on the beta-aryl, the para-substituted compounds resulted in the highest enantioselectivities (88-97% ee). The substituents on the benzoyl aryl of chalcone caused a decrease in the enantioselectivity compared to the unsubstituted case. The adducts with furyl or thiophenyl substituents were formed with >99% ee. The glucose-based catalyst also proved to be effective in the cases of diisopropyl and dibenzyl acetoxymalonates (including ees up to 99% ee). The reactions of diethyl acetoxymalonate with cyclic enones gave the corresponding Michael adducts with enantioselectivities up to 83%. The absolute configuration of one of the new Michael adducts was determined by CD spectroscopy. (C) 2016 Elsevier Ltd. All rights reserved.