ethyl 2-cyano-2-(3-oxocyclohexyl)-2-phenylacetate | 1292296-97-9

• 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: ethyl 2-cyano-2-(3-oxocyclohexyl)-2-phenylacetate
• 英文别名: Ethyl 2-cyano-2-(3-oxocyclohexyl)-2-phenylacetate
• CAS: 1292296-97-9
• 化学式: C₁₇H₁₉NO₃
• 分子量: 285.343
• InChiKey: DJAKCZNWCALQIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  67.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-环己烯-1-酮 、 苯基氰基乙酸乙酯 在 lithium phenolate 、 (S)-3,3′-bis[hydroxy(diphenyl)methyl]-1,1′-binaphthalene-2,2′-diol 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以90%的产率得到ethyl 2-cyano-2-(3-oxocyclohexyl)-2-phenylacetate
  参考文献：
  名称：

  Four hydroxyls are better than two. The use of a chiral lithium salt of 3,3′-bis-methanol-2,2′-binaphthol as a multifunctional catalyst of enantioselective Michael addition reactions

  摘要：

  The catalytic performance of the Li salt of (S)- or (R)-3,3'-bis[bis-(phenyl)hydroxymethyl]-2,2'-dihydroxy-dinaphthalene-1,1' (BIMBOL) in asymmetric Michael additions of malonic acid derivatives and toluedine has been studied. Nitrostyrene and cyclohex-2-enone were chosen as Michael acceptors. Efficient asymmetric C-C and C-N bond formations with ee's of up to 95% at room temperature were observed. A transition state model of the malonic ester addition to cyclohex-2-enone has been proposed based on the molecular structure of the acetone solvate of BIMBOL. The impact of the catalyst self-association on its performance is also discussed. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.12.003

文献信息

• Four hydroxyls are better than two. The use of a chiral lithium salt of 3,3′-bis-methanol-2,2′-binaphthol as a multifunctional catalyst of enantioselective Michael addition reactions
  作者：Yuri N. Belokon、Zalina T. Gugkaeva、Victor I. Maleev、Margarita A. Moskalenko、Alan T. Tsaloev、Victor N. Khrustalev、Karine V. Hakobyan

  DOI：10.1016/j.tetasy.2010.12.003

  日期：2011.1

  The catalytic performance of the Li salt of (S)- or (R)-3,3'-bis[bis-(phenyl)hydroxymethyl]-2,2'-dihydroxy-dinaphthalene-1,1' (BIMBOL) in asymmetric Michael additions of malonic acid derivatives and toluedine has been studied. Nitrostyrene and cyclohex-2-enone were chosen as Michael acceptors. Efficient asymmetric C-C and C-N bond formations with ee's of up to 95% at room temperature were observed. A transition state model of the malonic ester addition to cyclohex-2-enone has been proposed based on the molecular structure of the acetone solvate of BIMBOL. The impact of the catalyst self-association on its performance is also discussed. (C) 2010 Elsevier Ltd. All rights reserved.