2'-(cyclohex-1-enyl)acetanilide | 39212-30-1

• 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: 2'-(cyclohex-1-enyl)acetanilide
• 英文别名: N-acetyl-2-(cyclohex-1'-enyl)aniline；N-[2-(cyclohex-1-enyl)phenyl]acetamide；N-[2-(cyclohexen-1-yl)phenyl]acetamide
• CAS: 39212-30-1
• 化学式: C₁₄H₁₇NO
• 分子量: 215.295
• InChiKey: BIRLGWXWDNQTRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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：

  2'-(cyclohex-1-enyl)acetanilide 在 双氧水 作用下， 以 甲酸 为溶剂， 反应 24.0h， 以59%的产率得到6-(2-acetamidophenyl)-6-oxohexanoic acid
  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：

  环己酮 在 potassium cyanide 、 氢氧化钾 、 正丁基锂 作用下， 以 甲醇 为溶剂， 反应 7.0h， 生成 2'-(cyclohex-1-enyl)acetanilide
  参考文献：
  名称：

  Fleming, Ian; Loreto, Maria Antonietta; Wallace, Ian H.M., Journal of the Chemical Society. Perkin transactions I, 1986, p. 349 - 360

  摘要：

  DOI：

文献信息

• Amides as precursors of imidoyl radicals in cyclisation reactions
  作者：W. Russell Bowman、Anthony J. Fletcher、Jan M. Pedersen、Peter J. Lovell、Mark R.J. Elsegood、Elena Hernández López、Vickie McKee、Graeme B.S. Potts

  DOI：10.1016/j.tet.2006.10.030

  日期：2007.1

  Amides have been successfully used as precursors of imidoyl radicals for radical cyclisation. The amides have been converted to imidoyl selanides via reaction with phosgene to yield imidoyl chlorides followed by reaction with potassium phenylselanide. Imidoyl selanides were reacted with tributyltin hydride (Bu3SnH) as the radical mediator with triethylborane or AIBN as initiators to yield imidoyl radicals

  酰胺已成功地用作亚胺基自由基的前体，用于自由基环化。酰胺已通过与光气反应生成亚氨酰氯，然后与苯硒化钾反应，已转化为亚氨基酰硒化物。亚胺基硒化物与氢化三丁基锡（Bu 3 SnH）作为自由基介体反应，三乙基硼烷或AIBN作为引发剂，生成亚胺基自由基用于环化反应。酰亚胺基已被环化到烯烃上以产生2，3-取代的吲哚和-喹啉，并且还被吡咯和吲哚上以产生双环和三环杂芳烃。
• Cyclization ofN-acetyl-ortho-cycloalkenylanilines on treatment with bromine andN-bromosuccinimide
  作者：R. R. Gataullin、I. S. Afon'kin、A. A. Fatykhov、L. V. Spirikhin、I. B. Abdrakhmanov

  DOI：10.1007/bf02499076

  日期：1990.1
• ——
  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、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.
• FLEMING, I.;LORETO, M. A.;WALLACE, I. H. M.;MICHAEL, J. P., J. CHEM. SOC. PERKIN TRANS., 1986, N 2, 349-359
  作者：FLEMING, I.、LORETO, M. A.、WALLACE, I. H. M.、MICHAEL, J. P.

  DOI：——

  日期：——