N-(2-(naphthalen-2-yl)-2-oxoethyl)acetamide | 102440-80-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(2-(naphthalen-2-yl)-2-oxoethyl)acetamide
• 英文别名: N-(2-naphthalen-2-yl-2-oxo-ethyl)-acetamide；N-(2-[2]naphthyl-2-oxo-ethyl)-acetamide；N-(2-[2]Naphthyl-2-oxo-aethyl)-acetamid；2-Acetylamino-1-[2]naphthyl-aethanon；2-(N-Acetyl-glycyl)-naphthalin；N-[2-oxo-2-(2-naphthyl)ethyl]acetamide；N-(2-naphthalen-2-yl-2-oxoethyl)acetamide
• CAS: 102440-80-2
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: ITINLZUYCWDJAW-UHFFFAOYSA-N

物化性质

• 沸点：
  489.9±28.0 °C(predicted)
• 密度：
  1.171±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 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-(2-(naphthalen-2-yl)-2-oxoethyl)acetamide 在 aluminum isopropoxide 、 异丙醇 作用下， 生成 N-((1RS,2RS)-2-hydroxy-1-hydroxymethyl-2-[2]naphthyl-ethyl)-acetamide
  参考文献：
  名称：

  Chloromycetin.¹ Synthesis of DL-threo-2-Dichloroacetamido-1-(4-nitro-1-naphthyl)- 1,3-propanediol

  摘要：

  DOI：

  10.1021/ja01146a010
• 作为产物：
  描述：

  2-溴代-2-乙酰基萘 在 乌洛托品 、 sodium acetate 作用下， 以 水 、 乙酸酐 、 氯苯 为溶剂， 反应 14.5h， 生成 N-(2-(naphthalen-2-yl)-2-oxoethyl)acetamide
  参考文献：
  名称：

  TBAI-Catalyzed Oxidative Cross-Coupling of Phenols and 2-Aminoacetophenones

  摘要：

  An iodide-catalyzed oxidative cross-coupling between phenols and 2-aminoacetophenones has been developed. Using catalytic amounts of tetrabutylammoniumiodide (TBAI) as an iodine-containing catalyst and aqueous solutions of tert-butyl hydro-peroxide (TBHP) as the stoichiometric co-oxidant, a variety of alpha-phenoxylated 2-aminoacetophenones could be obtained in yields of up to 92% after remarkably short reaction times (20 min). This is a very rare example for an iodide-catalyzed intermolecular cross-coupling utilizing phenols. However, this efficient methodology could be further extended toward an intramolecular variant which gives direct access to a range of dihydro-4H-benzo[e][1,3]oxazin-4-ones.

  DOI：

  10.1021/acs.orglett.5b00466

文献信息

• Catalytic transformation of esters of 1,2-azido alcohols into α-amido ketones
  作者：Yongjin Kim、Han Kyu Pak、Young Ho Rhee、Jaiwook Park

  DOI：10.1039/c6cc02063a

  日期：——

  The esters of 1,2-azido alcohols were transformed into [small alpha]-amido ketones without external oxidants through the Ru-catalyzed formation of N-H imines with liberation of N2 followed by intramolecular migration of the...

  1,2-叠氮基醇的酯通过Ru催化形成的NH亚胺与N 2的释放而随后在分子内的迁移而转化为无外部氧化剂的小α-酰胺基酮。
• Potassium-Base-Mediated Autoxidative Diastereoselective Homocoupling of <i>N</i>-Acyl-2-aminoacetophenones
  作者：Yingwei Wang、Mingrong Yang、Chichou Lao、Zhihong Jiang

  DOI：10.1021/acs.orglett.2c00618

  日期：2022.4.15

  general and highly efficient method for the synthesis of dl-2,3-diamide-1,4-diones via autoxidative dehydrogenative homocoupling of N-acyl-2-aminoacetophenones mediated by t-BuOK. The transformation is mild, operationally simple, and environmentally friendly. Control experiments and stereochemical results suggest that the substrate undergoes autoxidation followed by a diastereoselective SN2 reactopm.

  我们在此报告了一种通用且高效的方法，用于通过由t -BuOK 介导的N-酰基-2-氨基苯乙酮的自氧化脱氢同源偶联来合成dl -2,3-diamide-1,4- diones。改造温和、操作简单、环保。对照实验和立体化学结果表明，底物发生自氧化，然后发生非对映选择性 S N 2 反应。
• Oxidative Cross-Coupling of α-Amino Ketones with Alcohols Enabled by I₂-Catalyzed C–H Hydroxylation
  作者：Yingwei Wang、Mingrong Yang、Chichou Lao、Hanxuan Wang、Zhihong Jiang

  DOI：10.1021/acs.joc.3c01469

  日期：2023.10.20

  oxidative cross-coupling of α-amino ketones with a wide range of alcohols is described. Using a combination of air and dimethyl sulfoxide (DMSO) as oxidants, the protocol allows an efficient synthesis of α-carbonyl N,O-acetals with high functional group tolerance and enables the late-stage introduction of α-amino ketones into biorelevant alcohols. Moreover, the present method can be used in the coupling of

  描述了α-氨基酮与多种醇的I 2催化氧化交叉偶联。该方案使用空气和二甲基亚砜（DMSO）的组合作为氧化剂，可以有效合成具有高官能团耐受性的α-羰基N,O-缩醛，并能够在后期将α-氨基酮引入生物相关醇中。此外，该方法可用于α-氨基酮与其他种类的亲核试剂的偶联，这对于α-氨基酮的官能化具有很大的通用性。初步的机理研究表明，α-氨基酮的 C-H 羟基化已被认为是随后脱水偶联的关键步骤。
• Visible-light-induced Ritter-type amidation of α-hydroxy ketones in the selective synthesis of α,α-diamido and monoamido ketones
  作者：Enrong Tang、Quan-Quan Zhou、Jie-Ping Wan

  DOI：10.1039/d4cc02334j

  日期：——

  Visible light-induced, transition metal-free oxidative dehydroxylation and C–H amidation of α-hydroxy ketones involving Ritter-type amidation has been developed, leading to the selective synthesis of α,α-diamido- and α-monoamido ketones with tunable selectivity as well as broad substrate tolerance.

  开发了可见光诱导、无过渡金属的氧化脱羟基和涉及 Ritter 型酰胺化的 α-羟基酮的 C-H 酰胺化，从而可以选择性合成具有可调选择性的 α,α-二酰胺基和 α-单酰胺基酮以及广泛的基材耐受性。
• Sytsch, Ukrainskij Khimicheskij Zhurnal, 1958, vol. 24, p. 79,87
  作者：Sytsch

  DOI：——

  日期：——