N-(3-oxocyclohexyl)-2-phenylacetamide | 1107665-17-7

• 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: N-(3-oxocyclohexyl)-2-phenylacetamide
• CAS: 1107665-17-7
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: FHCHFCVUFRFCSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(3-oxocyclohexyl)-2-phenylacetamide 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 12.0h， 生成 、
  参考文献：
  名称：

  功能化酮的 Baeyer-Villiger 氧化中区域选择性和对映选择性的催化剂控制

  摘要：

  我们报告了一种基于肽的催化剂，它可以强烈影响带有酰胺、尿素或磺酰胺官能团的环酮的 Baeyer-Villiger (BV) 氧化的区域和对映选择性。两种类型的选择性都被认为是由催​​化剂-底物氢键相互作用引起的。此外，在选定的情况下，反应表现出平行动力学分辨率的标志。在不对称过程中使用催化在 BV 产品之间进行选择的能力可能对复杂分子（包括天然产品）的合成和多样化具有广泛的用途。

  DOI：

  10.1021/ja508757g
• 作为产物：
  描述：

  3-N-叔丁氧羰基氨基环己酮 在 碳酸氢钠 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 N-(3-oxocyclohexyl)-2-phenylacetamide
  参考文献：
  名称：

  Divergent Stereoselectivity in Phosphothreonine (pThr)-Catalyzed Reductive Aminations of 3-Amidocyclohexanones

  摘要：

  Phosphothreonine (pThr)-embedded peptide catalysts are found to mediate the reductive amination of 3-amidocyclohexanones with divergent selectivity. The choice of peptide sequence can be used to alter the diastereoselectivity to favor either the cis-product or trans-product, which are obtained in up to 93:7 er. NMR studies and DFT calculations are reported and indicate that both pathways rely on secondary interactions between substrate and catalyst to achieve selectivity. Furthermore, catalysts appear to accomplish a parallel kinetic resolution of the substrates. The facility for phosphopeptides to tune reactivity and access multiple products in reductive aminations may translate to the diversification of complex substrates, such as natural products, at numerous reactive sites.

  DOI：

  10.1021/acs.joc.8b00207

文献信息

• Efficient Brønsted acid-catalyzed aza-Michael reaction of amides and ureas with α,β-unsaturated enones under high-pressure conditions
  作者：Saleha Azad、Tomohiro Kobayashi、Keiji Nakano、Yoshiyasu Ichikawa、Hiyoshizo Kotsuki

  DOI：10.1016/j.tetlet.2008.10.082

  日期：2009.1

  A new strategy for the aza-Michael reaction of amides and ureas with α,β-unsaturated enones, which uses p-TsOH·H2O as an efficient and inexpensive catalyst under high-pressure conditions, has been developed.

  开发了一种新的策略，用于酰胺和脲与α，β-不饱和烯酮的aza-Michael反应，该方法在高压条件下使用p -TsOH·H 2 O作为一种高效且廉价的催化剂。
• Solvent-free Brønsted acid-catalyzed Michael addition of nitrogen- and carbon-containing nucleophiles by ultrasound activation
  作者：Xiu-Jiang Du、Zhi-Peng Wang、Yan-Ling Hou、Cheng Zhang、Zheng-Ming Li、Wei-Guang Zhao

  DOI：10.1016/j.tetlet.2013.12.059

  日期：2014.1

  carbon-containing nucleophiles to cyclic enones. Using this conjugate addition reaction, a variety of different nucleophiles can react with a range of cyclic enones in the presence of p-toluenesulfonic acid under solvent-free ultrasound irradiation conditions affording the corresponding C–N or C–C adducts in good to excellent yields. Comparatively, performing the reaction under ultrasound irradiation gives

  已经开发出一种新的方法，用于将含氮和碳的亲核试剂迈克尔加成到环烯酮上。使用这种共轭加成反应，在对甲苯磺酸的存在下，无溶剂超声辐照条件下，多种不同的亲核试剂可以与多种环烯酮反应，从而提供相应的C–N或C–C加合物，且收率良好。 。相比之下，与在高压下进行反应相比，在超声辐射下进行反应可获得更高的产率，更有效且对环境无害。
• Divergent Stereoselectivity in Phosphothreonine (pThr)-Catalyzed Reductive Aminations of 3-Amidocyclohexanones
  作者：Christopher R. Shugrue、Aaron L. Featherston、Rachel M. Lackner、Angela Lin、Scott J. Miller

  DOI：10.1021/acs.joc.8b00207

  日期：2018.4.20

  Phosphothreonine (pThr)-embedded peptide catalysts are found to mediate the reductive amination of 3-amidocyclohexanones with divergent selectivity. The choice of peptide sequence can be used to alter the diastereoselectivity to favor either the cis-product or trans-product, which are obtained in up to 93:7 er. NMR studies and DFT calculations are reported and indicate that both pathways rely on secondary interactions between substrate and catalyst to achieve selectivity. Furthermore, catalysts appear to accomplish a parallel kinetic resolution of the substrates. The facility for phosphopeptides to tune reactivity and access multiple products in reductive aminations may translate to the diversification of complex substrates, such as natural products, at numerous reactive sites.
• Catalyst Control over Regio- and Enantioselectivity in Baeyer–Villiger Oxidations of Functionalized Ketones
  作者：David K. Romney、Sean M. Colvin、Scott J. Miller

  DOI：10.1021/ja508757g

  日期：2014.10.8

  We report a peptide-based catalyst that can strongly influence the regio- and enantioselectivity of the Baeyer–Villiger (BV) oxidation of cyclic ketones bearing amide, urea, or sulfonamide functional groups. Both types of selectivity are thought to arise from a catalyst–substrate hydrogen-bonding interaction. Furthermore, in selected cases, the reactions exhibit the hallmarks of parallel kinetic resolution

  我们报告了一种基于肽的催化剂，它可以强烈影响带有酰胺、尿素或磺酰胺官能团的环酮的 Baeyer-Villiger (BV) 氧化的区域和对映选择性。两种类型的选择性都被认为是由催​​化剂-底物氢键相互作用引起的。此外，在选定的情况下，反应表现出平行动力学分辨率的标志。在不对称过程中使用催化在 BV 产品之间进行选择的能力可能对复杂分子（包括天然产品）的合成和多样化具有广泛的用途。