5,5-Dimethyl-2-(4-morpholinyl)cyclohex-2-en-1-one | 144605-89-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,5-Dimethyl-2-(4-morpholinyl)cyclohex-2-en-1-one
• 英文别名: 5,5-Dimethyl-2-(morpholin-4-yl)cyclohex-2-en-1-one；5,5-dimethyl-2-morpholin-4-ylcyclohex-2-en-1-one
• CAS: 144605-89-0
• 化学式: C₁₂H₁₉NO₂
• 分子量: 209.288
• InChiKey: QURGLWHGMOVKOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  吗啉-4-基苯甲酸酯 、 3,3-二甲基环己酮 在 copper(II) nitrate trihydrate 、 二(4-溴苯基)胺 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以52%的产率得到5,5-Dimethyl-2-(4-morpholinyl)cyclohex-2-en-1-one
  参考文献：
  名称：

  通过铜和二芳基胺的协同催化作用，使未活化的环酮多功能化：获得环状α-烯胺

  摘要：

  首次报道了通过铜和二芳基胺的协同催化对环状α-烯胺酮直接合成的未活化环酮的多功能化。该反应经过氧化性α-氨基化反应，然后进行去饱和反应，反应条件温和，底物范围广，官能团耐受性强。

  DOI：

  10.1021/acs.orglett.8b00125

文献信息

• Reactions of enaminones with 1-nitroolefins. Scope and limitations of a polyquinane synthesis
  作者：John W. Huffman、Melanie M. Cooper、Barnabe B. Miburo、William T. Pennington

  DOI：10.1016/s0040-4020(01)80490-7

  日期：1992.1

  The reaction of several 2-aminocyclohex-2-en-1-ones with cyclic nitroolefins has been explored as a possible synthetic approach to polyquinanes. 2-Pyrrolidino, 2-piperidino and 2-morpholinocyclohex-2-en-1-one react with 1-nitrocyclopentene to provide substituted triquinanes. Reactions involving 5,5-dimethyl-2-morpholinocyclohex-2-en-1-one were unsuccessful as were those using 4,4-dimethyl-1-nitrocyclopentene. 5-Methyl-2-morpholinocyclohex-2-en-1-one and 1-nitrocyclopentene provide the corresponding triquinane, plus a by-product in which the amino substituent has been lost. The reactions of other selected nitroolefins have been carried out, and the products are described. The results of these reactions are rationalized in terms of an inverse electron demand Diels-Alder reaction to afford an intermediate oxazine N-oxide, which then undergoes further transformations to afford the observed products.
• Multifunctionalization of Unactivated Cyclic Ketones via Synergistic Catalysis of Copper and Diarylamine: Access to Cyclic α-Enaminone
  作者：Yang Li、Ran Zhang、Xihe Bi、Junkai Fu

  DOI：10.1021/acs.orglett.8b00125

  日期：2018.2.16

  A multifunctionalization of unactivated cyclic ketones via synergistic catalysis of copper and diarylamine for the direct synthesis of cyclic α-enaminone is reported for the first time. This reaction goes through oxidative α-amination, followed by a desaturation, and features mild reaction conditions, a broad substrate scope, and great functional group tolerance.

  首次报道了通过铜和二芳基胺的协同催化对环状α-烯胺酮直接合成的未活化环酮的多功能化。该反应经过氧化性α-氨基化反应，然后进行去饱和反应，反应条件温和，底物范围广，官能团耐受性强。