N-(2-(cyclopent-1-en-1-yl)phenyl)acetamide | 402509-25-5

• 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-1-en-1-yl)phenyl)acetamide
• 英文别名: N-acetyl-2-(cyclopent-1-en-1-yl)aniline；N-acetyl-2-(1-cyclopenten-1-yl)aniline；N-[2-(Cyclopent-1-en-1-yl)phenyl]acetamide；N-[2-(cyclopenten-1-yl)phenyl]acetamide
• CAS: 402509-25-5
• 化学式: C₁₃H₁₅NO
• 分子量: 201.268
• InChiKey: LNWVRTQCUKBZPB-UHFFFAOYSA-N

物化性质

• 沸点：
  389.6±31.0 °C(Predicted)
• 密度：
  1.135±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 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-1-en-1-yl)phenyl)acetamide 在 sodium tungstate 、 磷酸 、 双氧水 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以80%的产率得到2'-hydroxy-2-methylspiro[3,1-benzoxazine-4,1'-cyclopentane]
  参考文献：
  名称：

  Heterocyclization of N-[2-(cyclopent-1-enyl)phenyl]acetamides and ethyl N-[2-(cyclopent-1-enyl)phenyl]carbamates under the action of hydrogen peroxide

  摘要：

  DOI：

  10.1070/mc2001v011n05abeh001489
• 作为产物：
  描述：

  2-(cyclopent-1-en-1-yl)aniline 、 乙酸酐 以94%的产率得到N-(2-(cyclopent-1-en-1-yl)phenyl)acetamide
  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

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.
• Heterocyclization of N-[2-(cyclopent-1-enyl)phenyl]acetamides and ethyl N-[2-(cyclopent-1-enyl)phenyl]carbamates under the action of hydrogen peroxide
  作者：Rail R. Gataullin、Marat F. Nasyrov、Ol’ga V. Shitikova、Leonid V. Spirikhin、Il’dus B. Abdrakhmanov

  DOI：10.1070/mc2001v011n05abeh001489

  日期：2001.1
• Synthesis of derivatives of o-aminoacetophenone and o-aminobenzyl alcohol
  作者：R. R. Gataullin、I. B. Abdrakhmanov

  DOI：10.1134/s1070428007050132

  日期：2007.5

  Oxidation of 2'-hydroxy-8-methylspiro[4H-benz-1,3-oxazin-2-one-6,1'-cyclopentane] or N-mesyl-2-(cyclopent-1-en-1-yl)-6-methylaniline provided the corresponding ketones. The rearrangement of these ketones oximes under treatment with thionyl chloride gave rise to nitriles of 5-(2-amino-3-methylphenyl)-5-oxopentanoic or 5-(2-methanesulfamido-3-methylphenyl)-5-hydroxypentanoic acids. By heating 5-(2-acetylamido-3-methylphenyl)-5-oxopentanoic acid with LiH in THF3-(2,8-dimethylquinol-4-on-3-yl)propanoic acid was obtained.
• Reactions of N-acetyl- and N-ethoxycarbonyl-2-(1-cycloalken-1-yl)anilines with meta-cloroperbenzoic acid
  作者：A. Kh. Fattakhov、I. B. Abdrakhmanov、R. R. Gataullin

  DOI：10.1134/s1070363208080161

  日期：2008.8

  Reaction of N-ethoxycarbonyl-2-(1-cycloalken-1-yl)anilines with meta-cloroperbenzoic acid leads to the corresponding 2-[1-o-(3-chlorobenzoyl)-2-hydroxycyclopent-1-yl] anilines. 5-(2-Acetylaminophenyl)-5-oxopentanic or 6-oxohexanic acids are formed as main products in the reaction of N-acetyl-2-(1-cycloalken-1-yl)anilines with m-chloroperbenzoic acid in CH2Cl2. N-Acetyl-2-(1-cyclopenten-1-yl)-3,6-dimethylaniline is an exception in this series since its reaction stops at the stage of epoxide formation.
• ——
  作者：R. R. Gataullin、M. F. Nasyrov、E. V. Ivanova、N. N. Kabal'nova、I. B. Abdrakhmanov

  DOI：10.1023/a:1019696030069

  日期：——

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