N-acetyl-6-(cyclopent-1-enyl)-2-methylaniline | 235779-10-9

• 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-acetyl-6-(cyclopent-1-enyl)-2-methylaniline
• 英文别名: N-[2-(Cyclopent-1-en-1-yl)-6-methylphenyl]acetamide；N-[2-(cyclopenten-1-yl)-6-methylphenyl]acetamide
• CAS: 235779-10-9
• 化学式: C₁₄H₁₇NO
• 分子量: 215.295
• InChiKey: AZHHYCHQLVXDAG-UHFFFAOYSA-N

物化性质

• 沸点：
  377.8±31.0 °C(Predicted)
• 密度：
  1.112±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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-acetyl-6-(cyclopent-1-enyl)-2-methylaniline 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以99%的产率得到2,8-dimethylspiro[cyclopentane-1,4'-4'H-3,1-benzooxazine] hydrochloride
  参考文献：
  名称：

  Intramolecular cyclization ofN-acetyl-6-(cyclopent-1-enyl)-2-methylaniline

  摘要：

  N-Acetyl-6-(cyclopent-1-enyl)-2-methylaniline underwent intramolecular cyclization in the presence of HCl in CH2Cl2 at 20 degrees C to form 2,8-dimethylspiro[cyclopentane-1,4'-4'H- 3,1-benzooxazine] in quantitative yield.

  DOI：

  10.1007/bf02494577
• 作为产物：
  描述：

  2-methyl-6-(cyclopenten-2'-yl)aniline 在 氢氧化钾 作用下， 以 二氯甲烷 为溶剂， 反应 18.75h， 生成 N-acetyl-6-(cyclopent-1-enyl)-2-methylaniline
  参考文献：
  名称：

  Intramolecular cyclization ofN-acetyl-6-(cyclopent-1-enyl)-2-methylaniline

  摘要：

  N-Acetyl-6-(cyclopent-1-enyl)-2-methylaniline underwent intramolecular cyclization in the presence of HCl in CH2Cl2 at 20 degrees C to form 2,8-dimethylspiro[cyclopentane-1,4'-4'H- 3,1-benzooxazine] in quantitative yield.

  DOI：

  10.1007/bf02494577

文献信息

• ——
  作者：R. R. Gataullin、I. S. Afon'kin、A. A. Fatykhov、L. V. Spirikhin、I. B. Abdrakhmanov

  DOI：10.1023/a:1012413715466

  日期：——

  N-Acetyl- and N-formyl-ortho-alkenyl(cycloalkenyl)anilines were synthesized. Their reaction with P2O5 or PCl5 afforded quinolines. By reaction of the ortho-alkenyl(cycloalkenyl)anilines with 1-methylimino- or 1-phenylimino-1-chloroethanes amidines were obtained that were cyclized in the polyphosphoric acid. The reaction with the polyphosphoric acid of amidines prepared from alkenylanilines and 1-methylimino-1-chloroethane gave rise to 3-methyl-3,4-dihydroquinazolines; on replacing in the substrate methylimine group for phenylimine one the yield of quinazoline decreased.
• ——
  作者：R. R. Gataullin、M. F. Nasyrov、I. B. Abdrakhmanov、G. A. Tolstikov

  DOI：10.1023/a:1022572909355

  日期：——

  Heterocyclic compounds of the 4H-3,1-benzoxazine and cyclopenta[b]indole series were synthesized by oxydation of N-acyl derivatives of 2-(1-alkenyl)anilines with hydrogen peroxide. The structure of the oxidation products is determined by the reaction conditions, substituent in the ortho-position of the aromatic ring, protecting group, and alkenyl radical structure.
• ——
  作者：R. R. Gataullin、I. S. Afonkin、A. A. Fatykhov、L. V. Spirikhin、E. V. Tal"vinskii、I. B. Abdrakhmanov

  DOI：10.1023/a:1011312912357

  日期：——

  Electrophilic addition of HCl or Br-2 to N-acyl-2-(alk-2-enyl)anilines is accompanied by intramolecular cyclization of these amides to give 3,1-benzooxazine hydrochlorides or hydrobromides in high yields.
• ——
  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.
• 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