(E)-ethyl 2-(cyclohexylmethylene)-3-oxobutanoate | 958667-16-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: (E)-ethyl 2-(cyclohexylmethylene)-3-oxobutanoate
• 英文别名: ethyl (2E)-2-(cyclohexylmethylidene)-3-oxobutanoate
• CAS: 958667-16-8
• 化学式: C₁₃H₂₀O₃
• 分子量: 224.3
• InChiKey: IWIVMJMINWEYIY-FMIVXFBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.65
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 2-(cyclohexylmethylene)-3-oxobutanoate 、 N-亚苄基-4-甲基苯磺酰胺 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 以61%的产率得到ethyl 2-cyclohexyl-4-hydroxy-6-phenyl-1-tosyl-1,2,5,6-tetrahydropyridine-3-carboxylate
  参考文献：
  名称：

  Domino Imino-Aldol−Aza-Michael Reaction: One-Pot Diastereo- and Enantioselective Synthesis of Piperidines

  摘要：

  Addition of alpha-arylmethylidene- or alpha-alkylidene-beta-keto ester enolate to N-activated aldimines via the imino aldol pathway followed by intramolecular aza-Michael reaction in a domino fashion has been developed, and a highly diastereoselective route to substituted piperidines is reported. Enantiopure piperidines are synthesized from chiral sulfinyl imines. Formation and the observed stereoselectivity of the products have been rationalized by mechanistic and computational studies.

  DOI：

  10.1021/jo101680f
• 作为产物：
  描述：

  环己烷基甲醛 、 乙酰乙酸乙酯 、 溶剂黄146 生成 (E)-ethyl 2-(cyclohexylmethylene)-3-oxobutanoate
  参考文献：
  名称：

  POINDEXTER, GRAHAM S.;TEMPLE, DAVIS L.

  摘要：

  DOI：

文献信息

• Synthesis of Ethyl 5-Hydroxyisoxazolidine-4-carboxylates via Michael Addition/Intramolecular Hemiketalisation
  作者：Fides Benfatti、Andrea Bottoni、Giuliana Cardillo、Luca Gentilucci、Magda Monari、Elisa Mosconi、Marco Stenta、Alessandra Tolomelli

  DOI：10.1002/ejoc.200800719

  日期：2008.12

  The 1,4-addition of N,O-bis(trimethylsilyl)hydroxylamine to alkylideneacetoacetates gave, in high yield, new 5-hydroxyisoxazolidine-4-carboxylates. The results of the accurate computational investigation on the mechanism at the DFT level are in complete agreement with the experimental evidence and the crystallographic data. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

  N,O-双(三甲基甲硅烷基)羟胺与亚烷基乙酰乙酸酯的1,4-加成以高产率得到新的5-羟基异恶唑烷-4-羧酸酯。在 DFT 级别对机制进行精确计算研究的结果与实验证据和晶体学数据完全一致。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• Enzymatic resolution of ethyl 3-hydroxy-2(1′substituted-methylidene)-butyrate by Pseudomonas cepacia lipase catalyzed acetylation
  作者：Fides Benfatti、Giuliana Cardillo、Luca Gentilucci、Elisa Mosconi、Alessandra Tolomelli

  DOI：10.1016/j.tetasy.2007.09.002

  日期：2007.9

  Enzymatic resolution of a series of enantiomerically pure ethyl 3-hydroxy-2(1 ' substituted-methylidene)-butyrates was performed using Pseudomonas cepacia lipase (EC 3.1.1.3) as a catalyst. Optically active ethyl 3-hydroxy-2(1 ' substituted-methylidene)-butyrates, as well as their acetates, were obtained from this reaction in good yield and excellent enantiomeric excess. (c) 2007 Elsevier Ltd. All rights reserved.
• POINDEXTER, G. S.;TEMPLE, D. L. (JR)
  作者：POINDEXTER, G. S.、TEMPLE, D. L. (JR)

  DOI：——

  日期：——
• POINDEXTER, GRAHAM S.;TEMPLE, DAVIS L.
  作者：POINDEXTER, GRAHAM S.、TEMPLE, DAVIS L.

  DOI：——

  日期：——
• POINDEXTER, G. S.;TEMPLE, D. L.
  作者：POINDEXTER, G. S.、TEMPLE, D. L.

  DOI：——

  日期：——