1-acetyl-N-(2-methoxyphenyl)cyclopentanecarboxamide | 951000-04-7

• 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: 1-acetyl-N-(2-methoxyphenyl)cyclopentanecarboxamide
• 英文别名: 1-acetyl-N-(2-methoxyphenyl)cyclopentane-1-carboxamide
• CAS: 951000-04-7
• 化学式: C₁₅H₁₉NO₃
• 分子量: 261.321
• InChiKey: MAYQXUVXVKEBHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-acetyl-N-(2-methoxyphenyl)cyclopentanecarboxamide 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 40.0h， 以9%的产率得到3-(4-chlorobutyl)-8-methoxy-4-methylquinolin-2(1H)-one
  参考文献：
  名称：

  A New Efficient Synthesis of Pyranoquinolines from 1-Acetyl N-Aryl Cyclopentanecarboxamides

  摘要：

  A new efficient synthesis of pyrano[2,3-b]quinoline derivatives is developed via the H2SO4-mediated tandem cyclization/ring-opening/recyclization reaction of readily available 1-acetyl N-aryl cyclopentanecarboxamides, during which a novel ring-cleavage fashion of the cyclopentane unit is involved and possible mechanisms are discussed.

  DOI：

  10.1021/ol701536q
• 作为产物：
  描述：

  邻甲氧基苯胺 在 sodium acetate 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 37.0h， 生成 1-acetyl-N-(2-methoxyphenyl)cyclopentanecarboxamide
  参考文献：
  名称：

  Ligand-Enabled γ-C–H Olefination and Carbonylation: Construction of β-Quaternary Carbon Centers

  摘要：

  Monoselective gamma-C-H olefination and carbonylation of aliphatic acids has been accomplished by using a combination of a quinoline-based ligand and a weakly coordinating amide directing group. The reaction provides a new route for constructing richly functionalized all-carbon quaternary carbon centers at the beta-position of aliphatic acids.

  DOI：

  10.1021/ja501689j

文献信息

• Copper‐Catalyzed Regioselective Oxidative Cycloamidation of <i>α</i> ‐[( <i>β</i> ‐Dimethylamino)propenoyl]‐Alkylamides: Synthetic Route to Substituted Pyrrolidine‐2,4‐diones
  作者：Jingwen Yuan、Chitturi Bhujanga Rao、Yongjiu Liang、Rui Zhang、Qian Zhang、Liman Hou、Dewen Dong

  DOI：10.1002/adsc.201801237

  日期：2019.1.11

  An intramolecular oxidative amidation of varied α‐[(β‐dimethylamino)propenoyl]‐alkylamides catalyzed by copper(II) bromide in the presence of PIFA and TFA has been described. This process features mild reaction conditions, simple execution, good yields, high regioselectivity, and thereby, provides not only a facile and efficient protocol for the construction of C−N bond, but also a straightforward

  已经描述了在PIFA和TFA存在下，溴化铜（II）催化的各种α -[（β-二甲基氨基）丙烯酰基]-烷基酰胺的分子内氧化酰胺化反应。该过程的特点是反应条件温和，操作简单，收率高，区域选择性高，因此不仅为构建C-N键提供了简便有效的方法，而且为直接合成高密度取代的吡咯烷-2,4提供了简便的方法。 -diones。
• Vilsmeier-Type Reaction of Dimethylaminoalkenoyl Cyclopropanes: One-Pot Access to 2,3-Dihydrofuro [3,2-<i>c</i>]pyridin-4(5<i>H</i>)-ones
  作者：Peng Huang、Ning Zhang、Rui Zhang、Dewen Dong

  DOI：10.1021/ol203124f

  日期：2012.1.6

  A domino reaction of readily available 1-carbamoyl-1-dimethylaminoalkenoylcyclopropanes in the presence of triflic anhydride (Tf2O) in N,N-dimethylformamide (DMF) is described, which provides a facile one-pot access to 2,3-dihydrofuro[3,2-c]pyridin-4(5H)-ones via tandem formylation (Vilsmeier-type reaction), intramolecular cyclization, and ring-enlargement sequences.

  描述了在三氟甲磺酸酐（Tf 2 O）存在下于N，N-二甲基甲酰胺（DMF）中容易获得的1-氨基甲酰基-1-二甲基氨基链烯酰基环丙烷的多米诺反应，该反应可轻松地一锅获得2,3-二氢呋喃[3,2 - c ] pyridin-4（5 H）-通过串联甲酰化反应（Vilsmeier型反应），分子内环化和环扩大序列。
• PIFA-Mediated Oxidative Cyclization of 1-Carbamoyl-1-oximylcycloalkanes: Synthesis of Spiro-Fused Pyrazolin-5-one <i>N</i>-Oxides
  作者：Kewei Wang、Xiaolan Fu、Jinying Liu、Yongjiu Liang、Dewen Dong

  DOI：10.1021/ol802952e

  日期：2009.2.19

  A convenient and efficient synthesis of spiro-fused pyrazolin-5-one N-oxides starting from readily available 1-carbamoyl-1-oximylcycloalkanes is developed. This general protocol features a novel and facile way for access to the five-membered azaheterocycles by formation of a new N-N single bond. The key cyclization step utilizes the formation of an N-oxonitrenium intermediate, mediated by the hypervalent iodine reagent PIFA, and its subsequent intramolecular trapping by the amide moiety under rather mild experimental conditions.
• One-Pot Tandem Double-Aldol Reaction/Aza-Addition of Acetylacetamides and <i>o</i>-Phthalaldehyde Leading to Spiroindan-2,2′-pyrrolidines
  作者：Xin Cheng、Fushun Liang、Fan Shi、Lei Zhang、Qun Liu

  DOI：10.1021/ol802507y

  日期：2009.1.1

  A novel domino reaction based on o-phthalaldehyde and 3-oxo-N-arylbutanamide 1 has been developed which allows one-pot and efficient synthesis of structurally complex spiroindan-2,2'-pyrrolidines 2 and 3 with complete regioselectivity and high stereoselectivity from acyclic precursors.