(R)-diethyl-2-(1-(2-methoxyphenyl)-2-nitroethyl)malonate | 1355991-85-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (R)-diethyl-2-(1-(2-methoxyphenyl)-2-nitroethyl)malonate
• 英文别名: diethyl 2-[(1R)-1-(2-methoxyphenyl)-2-nitroethyl]propanedioate
• CAS: 1355991-85-3
• 化学式: C₁₆H₂₁NO₇
• 分子量: 339.345
• InChiKey: KEYXDHAFMJXTPO-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-(2-甲氧苯基)-2-硝基乙烯 、 丙二酸二乙酯 在 (1R,2R)-N1-(5,7-bis(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)-N2,N2-dimethylcyclohexane-1,2-diamine 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以94%的产率得到(R)-diethyl-2-(1-(2-methoxyphenyl)-2-nitroethyl)malonate
  参考文献：
  名称：

  Chiral 2-aminobenzimidazole bifunctional organocatalysts: effect of di-CF3 and TFA on catalytic mechanisms

  摘要：

  (S,S)-trans-Cyclohexanediamine-5,7-di-CF3-benzimidazole (3b) was developed as a new chiral bifunctional organocatalyst and successfully applied to Michael addition of diethyl malonate to nitroolefins (up to 99%, 98% ee) under neutral condition. Systematic investigation on the catalytic mechanism revealed that the role of the guanidine moiety and the dimethylamine moiety in catalysts might be reversed with respect to Bronsted/Lewis acidic or basic functionalities, depending on the reaction conditions (neutral or TFA co-catalyst). Generally, di-CF3 group substituted 2-aminobenzimidazole catalysts in neutral condition and non-substituted 2-aminobenzimidazole catalysts in co-catalyst (TFA) condition give high chemical yield and enantioselectivity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.12.021

文献信息

• Enantioselective organocatalytic Michael reactions using chiral (<i>R</i>,<i>R</i>)-1,2-diphenylethylenediamine-derived thioureas
  作者：Jae Ho Shim、Min Ji Lee、Min Ho Lee、Byeong-Seon Kim、Deok-Chan Ha

  DOI：10.1039/d0ra03550e

  日期：——

  Although the Michael addition is a very well-known and widely applied reaction, cost-effective, metal-free, and readily prepared organic catalysts remain rare. A chiral, bifunctional, (R,R)-1,2-diphenylethylenediamine-derived thiourea organic catalyst was developed and applied to asymmetric Michael additions of nitroalkenes under neutral conditions. Generally, fluorine-substituted thiourea catalysts

  尽管迈克尔加成反应是一种众所周知且应用广泛的反应，但具有成本效益、不含金属且易于制备的有机催化剂仍然很少见。开发了一种手性、双功能、( R , R )-1,2-二苯基乙二胺衍生的硫脲有机催化剂，并将其应用于中性条件下硝基烯烃的不对称迈克尔加成。通常，氟取代的硫脲催化剂在中性条件下表现出高化学产率和对映选择性。温和的反应对许多官能团具有耐受性，并提供了良好的产率，以及迈克尔加合物的高非对映和对映选择性。通过合成生物活性化合物 ( R )-Phenibut 证明了转化的效用。