N-acetyl-2-(cyclopent-2'-en-1'-yl)-6-methylaniline | 280576-13-8

• 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-2-(cyclopent-2'-en-1'-yl)-6-methylaniline
• 英文别名: N-acetyl-6-(cyclopent-2-enyl)-2-methylaniline；N-acetyl-2-methyl-6-(cyclopent-1-enyl)aniline；N-(2-cyclopent-2-en-1-yl-6-methylphenyl)acetamide
• CAS: 280576-13-8
• 化学式: C₁₄H₁₇NO
• 分子量: 215.295
• InChiKey: NAHXNGGWLABWKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 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-2-(cyclopent-2'-en-1'-yl)-6-methylaniline 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 反应 0.33h， 以91%的产率得到4-acetyl-(3-bromo-5-methyl-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole)
  参考文献：
  名称：

  Cyclization ofN-acetyl-ortho-cycloalkenylanilines on treatment with bromine andN-bromosuccinimide

  摘要：

  DOI：

  10.1007/bf02499076
• 作为产物：
  描述：

  3-iodo-5-methyl-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole 在 potassium carbonate 、 锌 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 N-acetyl-2-(cyclopent-2'-en-1'-yl)-6-methylaniline
  参考文献：
  名称：

  3-取代环戊二烯[b]吲哚的合成

  摘要：

  当与 I2 反应时，2-(环戊-2-烯基)苯胺以高产率环化成 3-碘-1,2,3,3a,4,8b-六氢环戊二烯并[b]吲哚。次要反应产物是 3,5- 或 3,7- 二碘二氢吲哚。3-iodo-5-methyl-1,2,3,3a,4,8b-hexahydro-cyclopenta[b]indole 或其 N-氯乙酰衍生物的氨解产生 3-amino-5-methyl-1,2,3, 3a,48b-六氢-和5-甲基-1,3a,4,8b-四氢环戊[b]吲哚。

  DOI：

  10.1007/bf02496351

文献信息

• Effect of substituents on isomerization of N-acyl-3-iodo-5-R-1,2,3,3a,4,8b-hexahydrocyclopenta[b]-indoles into 3,4,4a,8c-tetrahydro-2aH-2-oxa-8b-azoniapentaleno[1,6-ab]indenes
  作者：M. A. Bagamanova、R. R. Gataullin

  DOI：10.1134/s1070363215030147

  日期：2015.3

  Halocyclization of ortho-(2-cyclopenten-1-yl)aniline derivatives provided 3-halosubstituted cyclopenta[b]indoles. Some transformations of the latter were studied.
• Atropisomeric N-acyl-N-(cyclopentenylphenyl)glycines in the synthesis of oxazolo[3,4-a]benzoxazocinones
  作者：R. R. Gataullin、Z. A. Ibatullina、E. S. Meshcheryakova、A. A. Fatykhov、L. M. Khalilov

  DOI：10.1134/s1070428017050098

  日期：2017.5

  Intramolecular [3+2]-cycloaddition was studied of munchnones generated at heating syn- and anti-atropisomers of N-acyl-N-[6-methyl-2-(cyclopent-2-en-1-yl)phenyl]glycines with acetic anhydride. By spectral and X-ray diffraction analysis syn-isomers of acids and tetrahydro-1,4,7-methanetriyl[1,3]oxazolo[3,4-a][1]- bensazocin-3(3aH)-ones were identified.
• Synthesis of N-acetyl-3,3a,4,8b- and -1,3a,4,8b-tetrahydrocyclopenta[b]indoles from N- and 2-(cyclopent-2-en-1-yl)anilines
  作者：D. A. Skladchikov、R. S. Buranbaeva、A. A. Fatykhov、S. P. Ivanov、R. R. Gataullin

  DOI：10.1134/s1070428012120093

  日期：2012.12

  Reactions of 2-bromo-N-(cyclopent-2-en-1-yl)-4-methylaniline and N-(cyclopent-2-en-1-yl)-2-iodo-4,6-dimethylaniline with acetyl bromide in the presence of potassium carbonate gave mixtures of syn and anti atropisomers of the corresponding N-acetyl derivatives at ratios of 1: 1 and 3: 2 respectively. Heating of these mixtures in toluene in the presence of Pd(OAc)(2), PPh3, Et3N, and K2CO3 (KOAc) afforded mixtures of isomeric N-acetyl-7-methyl-3,3a,4,8b- and -1,3a,4,8b-tetrahydrocyclopenta[b]indoles at a ratio of 3: 1 or N-acetyl-5,7-dimethyl-3,3a,4,8b- and -1,3a,4,8b-tetrahydrocyclopenta[b]indoles at a ratio of 2: 3. N-Acetyl-3,3a,4,8b-tetrahydrocyclopenta[b]indole was found to undergo thermal isomerization into N-acetyl-1,3a,4,8btetrahydrocyclopenta[b]indole.
• ——
  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、T. V. Kazhanova、R. I. Galeeva、A. A. Fatykhov、L. V. Spirikhin、I. B. Abdrakhmanov

  DOI：10.1023/a:1012760303749

  日期：——

  Oxidation of N- and C-alkenylanilines with ozone under conditions of alcohol formation was studied. Depending on the structure of the alkenyl moiety, the reaction yields aryl-substituted propanols, pentanediols, or tetrahydropyran.