4-(Naphthalen-2-yl)azetidin-2-one | 777884-18-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 4-(Naphthalen-2-yl)azetidin-2-one
• 英文别名: 4-naphthalen-2-ylazetidin-2-one
• CAS: 777884-18-1
• 化学式: C₁₃H₁₁NO
• 分子量: 197.236
• InChiKey: GQEDXQUOFZBICX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(Naphthalen-2-yl)azetidin-2-one 在 劳森试剂 作用下， 以 四氢呋喃 为溶剂， 反应 1.33h， 生成 4-(2'-naphthyl)-1-azetidin-2-thione
  参考文献：
  名称：

  Pyridines from Azabicyclo[3.2.0]hept-2-en-4-ones through a Proposed Azacyclopentadienone

  摘要：

  Pyridines have been formed by heating azabicyclo[3.2.0]hept-2-en-4-ones in toluene. The generation of a 3-azacyclopentadienone intermediate via a [2 + 2]-cycloreversion Is proposed as the key step. A Diels-Alder reaction of a styrene, extrusion of carbon monoxide, and loss of hydrogen then gives the pyridine. The process parallels the well-known synthesis of benzenes from cyclopentadienones. The azabicyclo[3.2.0]hept-2-en-4-ones were synthesized from the reaction between readily available cyclopropenones and 1-azetines, In which the cyclopropenones behave as all-carbon 1,3-dipolar equivalents.

  DOI：

  10.1021/ol202924s
• 作为产物：
  描述：

  氯磺酰异氰酸酯 、 2-乙烯基萘 以 乙醚 为溶剂， 生成 4-(Naphthalen-2-yl)azetidin-2-one
  参考文献：
  名称：

  连续可见光诱导电子转移对环胺中 C−N 键与 CO2 的光催化羧基化

  摘要：

  通过连续光诱导电子转移 (ConPET) 实现环胺中 C-N 键与 CO 2的光催化羧化。这种温和且不含过渡金属的方案为有价值的 β-、γ-、δ- 和 ε- 氨基酸提供了一条通用且实用的途径。

  DOI：

  10.1002/anie.202217918

文献信息

• Catalytic, Enantioselective N-Acylation of Lactams and Thiolactams Using Amidine-Based Catalysts
  作者：Xing Yang、Valentina D. Bumbu、Peng Liu、Ximin Li、Hui Jiang、Eric W. Uffman、Lei Guo、Wei Zhang、Xuntian Jiang、K. N. Houk、Vladimir B. Birman

  DOI：10.1021/ja306766n

  日期：2012.10.24

  contrast to alcohols and amines, racemic lactams and thiolactams cannot be resolved directly via enzymatic acylation or classical resolution. Asymmetric N-acylation promoted by amidine-based catalysts, particularly Cl-PIQ 2 and BTM 3, provides a convenient method for the kinetic resolution of these valuable compounds and often achieves excellent levels of enantioselectivity in this process. Density

  与醇和胺不同，外消旋内酰胺和硫内酰胺不能通过酶促酰化或经典拆分直接拆分。由脒基催化剂，特别是 Cl-PIQ 2 和 BTM 3 促进的不对称 N-酰化，为这些有价值的化合物的动力学拆分提供了一种方便的方法，并且通常在该过程中实现了出色的对映选择性。密度泛函理论计算表明，反应通过内酰胺互变异构体的 N-酰化发生，阳离子-π 相互作用在内酰胺底物的手性识别中起关键作用。
• Visible-Light Photocatalytic Barbier-Type Reaction of Aziridines and Azetidines with Nonactivated Aldehydes
  作者：Quan Qu、Lin Chen、Yong-Yuan Gui、Da-Gang Yu、Yu Deng

  DOI：10.1055/a-2039-9942

  日期：——

  restricts their widespread application. Considering the ready availability and diversity of cyclic amines, we report a visible-light photocatalytic Barbier-type reaction of aziridines and azetidines with nonactivated aldehydes. A series of important γ- and δ-amino alcohols were synthesized in the presence of amines as electron donors. Moreover, this transition-metal-free protocol displays mild reaction

  Barbier 型反应是一组经典的碳-碳键形成反应；然而，它们对化学计量金属的普遍使用限制了它们的广泛应用。考虑到环胺的易得性和多样性，我们报告了氮丙啶和氮杂环丁烷与未活化醛的可见光光催化 Barbier 型反应。在胺作为电子供体存在的情况下，合成了一系列重要的 γ- 和 δ- 氨基醇。此外，这种不含过渡金属的方案显示出温和的反应条件、广泛的官能团耐受性和广泛的底物范围。机理研究表明，碳自由基和负碳离子可能作为关键中间体产生。
• 1,2,4-Oxadiazoles from cycloreversions of oxadiazabicyclo[3.2.0]heptenes: 1-azetines as thiocyanate equivalents
  作者：Karl Hemming、Musharraf N. Khan、Paul A. O'Gorman、Arnaud Pitard

  DOI：10.1016/j.tet.2012.12.007

  日期：2013.1

  1,3-Dipolar cycloaddition of nitrile oxides to 4-aryl-2-alkylthio-1-azetines gave a series of oxadiazabicyclo[3.2.0]heptenes as single diastereoisomers. Heating these cycloadducts in toluene resulted in an overall [2+2]-cycloreversion to give 5-alkylthio-3-aryl-1,2,4-oxadiazoles. In this process, the 1-azetine behaves as a thiocyanate equivalent. When the nitrile oxide substituent was 2-azidobenzene, the azide could be converted into a 1,2,3-triazole giving a (1,2,4-oxadiazolo)-(1,2,3-triazolo)-1,2-disubstituted benzene. 1,2,4-Oxadiazoles are sought after in medicinal chemistry and materials sciences. (c) 2012 Elsevier Ltd. All rights reserved.
• The acid-mediated ring opening/cyclisation reaction of N-benzyl-α-aryl-azetidinones
  作者：Frank D. King、Stephen Caddick

  DOI：10.1016/j.tet.2012.09.046

  日期：2012.11

  N-Benzyl-4-aryl-azetidinones undergo ring opening with triflic acid to form N-benzyl-cinnamamides, which either undergo cyclisation to give 5-aryl-benzazepin-3-ones or N-debenzylation to give cinnamamides. (C) 2012 Elsevier Ltd. All rights reserved.
• Kinetic Resolution of β-Lactams via Enantioselective N-Acylation
  作者：Xing Yang、Valentina D. Bumbu、Vladimir B. Birman

  DOI：10.1021/ol201911z

  日期：2011.9.16

  Enantioselective N-acylation of 4-aryl-beta-lactams in the presence of acyl transfer catalyst CI-PIQ provides an effective method for their nonenzymatic kinetic resolution.