N,N-二环己基-2-氧代-2-苯基乙酰胺 | 89595-72-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N,N-二环己基-2-氧代-2-苯基乙酰胺
• 英文名称: N,N-Dicyclohexyl-I+/--oxobenzeneacetamide
• 英文别名: N,N-dicyclohexyl-2-oxo-2-phenylacetamide
• CAS: 89595-72-2
• 化学式: C₂₀H₂₇NO₂
• 分子量: 313.44
• InChiKey: GAYQPNSSMXUMMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-二环己基-2-氧代-2-苯基乙酰胺 反应 15.0h， 以57%的产率得到1-Cyclohexyl-3-hydroxy-3-phenyl-1-aza-spiro[3.5]nonan-2-one
  参考文献：
  名称：

  Toda, Fumio; Miyamoto, Hisakazu, Journal of the Chemical Society. Perkin transactions I, 1993, # 10, p. 1129 - 1132

  摘要：

  DOI：
• 作为产物：
  描述：

  苯基丙醇水合物 、 二环己胺 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 0.33h， 以26%的产率得到N,N-二环己基-2-氧代-2-苯基乙酰胺
  参考文献：
  名称：

  Selenium dioxide-mediated synthesis of α-ketoamides from arylglyoxals and secondary amines

  摘要：

  A facile and expeditious synthetic approach for the synthesis of alpha-ketoamides 3 is described. A series of alpha-ketoamides 3 was synthesized via reaction of selenium dioxide-mediated oxidative amidation between arylglyoxals 1 and secondary amines 2, and accelerated with microwave irradiation. Our findings indicate that constrained amines, such as piperazine and piperidine exhibit higher conversions for this transformation. This reaction was explored by synthesizing a series of alpha-ketoamides 3 from various arylglyoxals 1 with cyclic and acyclic secondary amines 2. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.05.136

文献信息

• Asymmetric induction during photocyclization of chiral and achiral α-oxoamides within achiral zeolites
  作者：Arunkumar Natarajan、V. Ramamurthy

  DOI：10.1039/b611387g

  日期：——

  gamma-hydrogen transfer. While in benzene the major product is oxazolidinone, within an MY zeolite, the main product is a beta-lactam. In this investigation, we have focused our attention on asymmetric induction in the formation of the beta-lactam product. Two approaches--using a chiral inductor and chiral auxiliary--have been employed. While in solution, in the presence of chiral inductors, achiral

  已经在沸石中研究了能够进行γ-氢转移的31种α-氧代酰胺的光化学反应。激发后，这些分子在溶液中产生两种产物-β-内酰胺和恶唑烷酮-两者都是由γ-氢转移产生的。苯中的主要产物是恶唑烷酮，而MY沸石中的主要产物是β-内酰胺。在这项研究中，我们将注意力集中在β-内酰胺产物形成中的不对称诱导上。已经采用了两种方法-使用手性感应剂和手性辅助剂。在溶液中，在手性诱导剂的存在下，非手性α-氧酰胺可产生对映选择性为零的β-内酰胺。在沸石中，ee高达44％。带有手性助剂的α-氧代酰胺在溶液中对β-内酰胺的非对映选择性低于5％，而在沸石中，相同的α-氧代酰胺使产品的de's高达83％。沸石的如此显着影响归因于碱金属离子与反应物α-氧代酰胺的相互作用以及沸石内部的封闭环境。在这一阶段，我们还不能提供具有预测能力的模型，需要进一步的工作来理解这种有价值的非对称归纳策略。
• Toda, Fumio; Miyamoto, Hisakazu; Matsukawa, Rikiya, Journal of the Chemical Society. Perkin transactions I, 1992, # 12, p. 1461 - 1462
  作者：Toda, Fumio、Miyamoto, Hisakazu、Matsukawa, Rikiya

  DOI：——

  日期：——
• Selenium dioxide-mediated synthesis of α-ketoamides from arylglyoxals and secondary amines
  作者：Arthur Y. Shaw、Christine R. Denning、Christopher Hulme

  DOI：10.1016/j.tetlet.2012.05.136

  日期：2012.8

  A facile and expeditious synthetic approach for the synthesis of alpha-ketoamides 3 is described. A series of alpha-ketoamides 3 was synthesized via reaction of selenium dioxide-mediated oxidative amidation between arylglyoxals 1 and secondary amines 2, and accelerated with microwave irradiation. Our findings indicate that constrained amines, such as piperazine and piperidine exhibit higher conversions for this transformation. This reaction was explored by synthesizing a series of alpha-ketoamides 3 from various arylglyoxals 1 with cyclic and acyclic secondary amines 2. (C) 2012 Elsevier Ltd. All rights reserved.
• Toda, Fumio; Miyamoto, Hisakazu, Journal of the Chemical Society. Perkin transactions I, 1993, # 10, p. 1129 - 1132
  作者：Toda, Fumio、Miyamoto, Hisakazu

  DOI：——

  日期：——