N-(2-(cyclopent-2-en-1-yl)phenyl)acetamide | 126087-55-6

• 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-(2-(cyclopent-2-en-1-yl)phenyl)acetamide
• 英文别名: N-acetyl-2-(cyclopent-2-en-1-yl)aniline；N-acetyl-2-(cyclopent-2-enyl)aniline；N-[2-(Cyclopent-2-en-1-yl)phenyl]acetamide；N-(2-cyclopent-2-en-1-ylphenyl)acetamide
• CAS: 126087-55-6
• 化学式: C₁₃H₁₅NO
• 分子量: 201.268
• InChiKey: XDWCIAZISUIERM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  N-(2-(cyclopent-2-en-1-yl)phenyl)acetamide 在 sodium tungstate 、 磷酸 、 双氧水 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以45%的产率得到N-acetyl-2-(2,3-epoxycyclopent-1-yl)aniline
  参考文献：
  名称：

  摘要：

  Treatment of the ozonization products from N-acetyl- or 2-methyl-N-trifluoroacetyl-6-(cyclopent-1-enyl)anilines with NaBH4 gives 6-methyl-2-tetrahydropyranylaniline. When treated with Me2S, the ozonization products yield the corresponding oxoaldehyde dimethyl acetals. The oxidation of N-acetyl-2-(cyclopent-1-enyl)- or -(cyclohex-1-ellyl)anilines with H2O2 in HCOOH affords omega-(2-acetamidophenyl)-5-oxopentanoic or -6-oxohexanoic acid, respectively. The reaction of N-acetyl-2-(cyclopent-1-enyl)aniline with H2O2 in the presence of Na2WO4 and H3PO4 gives 3,1-benzooxazine in high yield.

  DOI：

  10.1023/a:1015074016576
• 作为产物：
  描述：

  2-碘乙酰苯胺 、 环戊烯 在 palladium diacetate 四丁基氯化铵 、 potassium acetate 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以76%的产率得到N-(2-(cyclopent-2-en-1-yl)phenyl)acetamide
  参考文献：
  名称：

  钯催化的环烯烃分子间芳基化反应的改进方法

  摘要：

  钯催化芳基卤化物和环状烯烃的分子间烯丙基交叉偶联的改进方法可抑制双键异构化并容纳许多重要的官能团。

  DOI：

  10.1016/s0040-4039(00)99075-0

文献信息

• Controlling Olefin Isomerization in the Heck Reaction with Neopentyl Phosphine Ligands
  作者：Matthew G. Lauer、Mallory K. Thompson、Kevin H. Shaughnessy

  DOI：10.1021/jo501840u

  日期：2014.11.21

  The use of neopentyl phosphine ligands was examined in the coupling of aryl bromides with alkenes. Di-tert-butylneopentylphosphine (DTBNpP) was found to promote Heck couplings with aryl bromides at ambient temperature. In the Heck coupling of cyclic alkenes, the degree of alkene isomerization was found to be controlled by the choice of ligand with DTBNpP promoting isomerization to a much greater extent than trineopentylphosphine (TNpP). Under optimal conditions, DTBNpP provides high selectivity for 2-aryl-2,3-dihydrofuran in the arylation of 2,3-dihydrofuran, whereas TNpP provided high selectivity for the isomeric 2-aryl-2,5-dihydrofuran. A similar complementary product selectivity is seen in the Heck coupling of cyclopentene. Heck coupling of 2-bromophenols or 2-bromoanilides with 2,3-dihydrofurans affords 2,5-epoxybenzoxepin and 2,5-epoxybenzazepins, respectively.
• ——
  作者：A. G. Mustafin、D. I. Dyachenko、R. R. Gataullin、G. Yu. Ishmuratov、R. Ya. Kharisov、I. B. Abdrakhmanov、G. A. Tolstikov

  DOI：10.1023/a:1024477115507

  日期：——

  Ozonolysis of N-acyl-2-(1-methylbut-2-enyl)- and N-acyl-2-(cyclopent-2-enyl)anilines followed by treatment with NaBH4 afforded the corresponding 2-(2-hydroxyethyl-1-methyl) and 2-(1,5-dihydroxypent-2-yl) derivatives. The reaction can be directed to indole derivatives by varying the nature of both the acyl group and reducing reagent.
• Ozonolysis of N-acetyl-2-(cyclopent-2-enyl)aniline
  作者：Akhat G. Mustafin、Denis I. D’yachenko、Tat’yana V. Khakimova、Leonid V. Spirikhin、Gumer Yu. Ishmuratov、Il’dus B. Abdrakhmanov、Genrikh A. Tolstikov

  DOI：10.1070/mc2001v011n04abeh001444

  日期：2001.1
• Improved procedures for the palladium-catalyzed intermolecular arylation of cyclic alkenes
  作者：Richard C. Larock、William H. Gong、Bruce E. Baker

  DOI：10.1016/s0040-4039(00)99075-0

  日期：1989.1

  Improved procedures for the palladium-catalyzed, intermolecular, allylic cross-coupling of aryl halides and cyclic alkenes inhibit double-bond isomerization and accommodate many important functional groups.

  钯催化芳基卤化物和环状烯烃的分子间烯丙基交叉偶联的改进方法可抑制双键异构化并容纳许多重要的官能团。
• ——
  作者：R. R. Gataullin、M. F. Nasyrov、D. I. D"yachenko、A. A. Fatykhov、O. V. Shitikova、L. V. Spirikhin、I. B. Abdrakhmanov

  DOI：10.1023/a:1015074016576

  日期：——

  Treatment of the ozonization products from N-acetyl- or 2-methyl-N-trifluoroacetyl-6-(cyclopent-1-enyl)anilines with NaBH4 gives 6-methyl-2-tetrahydropyranylaniline. When treated with Me2S, the ozonization products yield the corresponding oxoaldehyde dimethyl acetals. The oxidation of N-acetyl-2-(cyclopent-1-enyl)- or -(cyclohex-1-ellyl)anilines with H2O2 in HCOOH affords omega-(2-acetamidophenyl)-5-oxopentanoic or -6-oxohexanoic acid, respectively. The reaction of N-acetyl-2-(cyclopent-1-enyl)aniline with H2O2 in the presence of Na2WO4 and H3PO4 gives 3,1-benzooxazine in high yield.