(-)-2-[(2-oxocyclohexyl)phenylmethyl]malonic acid diethyl ester | 86661-22-5

• 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: (-)-2-[(2-oxocyclohexyl)phenylmethyl]malonic acid diethyl ester
• 英文别名: (-)-(1'S,1''S)-<(2-Oxocyclohexyl)phenylmethyl>propandisaeure-diethylester；diethyl 2-[(S)-[(1S)-2-oxocyclohexyl]-phenylmethyl]propanedioate
• CAS: 86661-22-5
• 化学式: C₂₀H₂₆O₅
• 分子量: 346.423
• InChiKey: XDPMGXBLENAVEC-WBVHZDCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (S)-2-methoxymethylpyrrolidine cyclohexanone enamine 、 亚苯甲基丙二酸二乙酯 以70%的产率得到
  参考文献：
  名称：

  BLARER, S. J.;SEEBACH, D., CHEM. BER., 1983, 116, N 6, 2250-2260

  摘要：

  DOI：

文献信息

• Catalytic enantioselective direct Michael additions of ketones to alkylidene malonates
  作者：Juan M Betancort、Kandasamy Sakthivel、Rajeswari Thayumanavan、Carlos F Barbas

  DOI：10.1016/s0040-4039(01)00793-6

  日期：2001.7

  Enantioselective direct Michael additions of ketones using (S)-1-(2-pyrrolidinylmethyl)-pyrrolidine as a catalyst are described. Michael adducts with up to 91% e.e. were obtained by the reaction of alkylidene malonates with simple unactivated ketones under mild reaction conditions.

  描述了使用（S）-1-（2-吡咯烷基甲基）-吡咯烷作为催化剂对酮的对映选择性直接迈克尔加成。通过在温和的反应条件下，亚烷基丙二酸酯与简单的未活化酮反应，可得到ee高达91％的迈克尔加合物。
• Enantioselectively Organocatalytic Michael Addition of Ketones to Alkylidene Malonates
  作者：Chun-Li Cao、Xiu-Li Sun、Jiao-Long Zhou、Yong Tang

  DOI：10.1021/jo070070p

  日期：2007.5.1

  An organocatalytic asymmetric Michael addition of ketones to alkylidene malonates has been developed. In the presence of 20 mol % of urea 1a or N-(pyrrolidin-2-ylmethyl)trifluoromethanesulfonamide 1j, the reactions of ketones with alkylidene malonates afford the desired Michael adducts in moderate to good yields with good to high enantioselectivities under mild conditions.

  已经开发了酮的有机催化不对称迈克尔加成到亚烷基丙二酸酯。在20mol％的尿素1a或N-（吡咯烷基-2-基甲基）三氟甲磺酰胺1j的存在下，酮与亚烷基丙二酸酯的反应以中等至良好的产率提供所需的迈克尔加合物，并在温和的条件下具有良好至高的对映选择性。
• Solvent free, fast and asymmetric Michael additions of ketones to nitroolefins using chiral pyrrolidine–pyridone conjugate bases as organocatalysts
  作者：Chandan K. Mahato、Mrinalkanti Kundu、Animesh Pramanik

  DOI：10.1016/j.tetasy.2017.03.002

  日期：2017.4

  New chiral organocatalysts are envisaged based on a pyrrolidine-pyridone conjugate and synthesized from commercially available proline employing standard protocols. These catalysts were found to be useful for asymmetric Michael additions of ketones to nitroolefins to afford the desired products in very good yields (up to 98%) with excellent diastereo- and enantioselectivities (>97:3 syn/anti and up to 98% ee) in very short reaction time compared with the existing reports. (C) 2017 Elsevier Ltd. All rights reserved.
• Betancort, Juan M.; Sakthivel, Kandasamy; Thayumanavan, Rajeswari, Synthesis, 2004, # 9, p. 1509 - 1521
  作者：Betancort, Juan M.、Sakthivel, Kandasamy、Thayumanavan, Rajeswari、Tanaka, Fujie、Barbas III, Carlos F.

  DOI：——

  日期：——
• Blarer, Stefan J.; Seebach, Dieter, Chemische Berichte, 1983, vol. 116, # 6, p. 2250 - 2260
  作者：Blarer, Stefan J.、Seebach, Dieter

  DOI：——

  日期：——