N-[2-(1-cyclopenten-3-yl)-4-methylphenyl]acetamide | 1408382-13-7

• 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-(1-cyclopenten-3-yl)-4-methylphenyl]acetamide
• 英文别名: N-[2-(1-cyclopenten-3-yl)-4-methylphenyl]acet-amide；N-(2-cyclopent-2-en-1-yl-4-methylphenyl)acetamide
• CAS: 1408382-13-7
• 化学式: C₁₄H₁₇NO
• 分子量: 215.295
• InChiKey: QICJTWAWFHWRBV-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-[2-(1-cyclopenten-3-yl)-4-methylphenyl]acetamide 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 为溶剂， 反应 24.0h， 以69%的产率得到(3R*,3aR*,8bS*)-N-acetyl-3-bromo-7-methyl-1,2,3,3,4,8b-hexahydrocyclopenta[b]indole
  参考文献：
  名称：

  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

  摘要：

  Halocyclization of ortho-(2-cyclopenten-1-yl)aniline derivatives provided 3-halosubstituted cyclopenta[b]indoles. Some transformations of the latter were studied.

  DOI：

  10.1134/s1070363215030147

文献信息

• Reactions of N- and C-alkenylanilines: IX. Synthesis, oxidation, and nitration of some 7-methyl-1,3a,4,8b-tetrahydrocyclopenta[b]indoles
  作者：D. A. Skladchikov、K. Yu. Suponitskii、I. B. Abdrakhmanov、R. R. Gataullin

  DOI：10.1134/s1070428012070123

  日期：2012.7

  Heating of 4-acyl-3-iodo-7-methyl-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indoles in piperidine gave 4-acyl-7-methyl-1,3a,4,8b-tetrahydrocyclopenta[b]indoles which were oxidized with KMnO4 to obtain the corresponding 4-acyl-7-methyl-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole-1,2-diols. Oxidation of 4-acyl-7-methyl-1,3a,4,8b-tetrahydrocyclopenta[b]indoles at the olefinic double bond with hydrogen peroxide

  在哌啶中加热4-酰基-3-碘-7-甲基-1,2,3,3a，4,8b-六氢环戊[ b ]吲哚得到4-酰基-7-甲基-1,3a，4,8b-用KMnO4氧化得到四氢环戊[ b ]吲哚，得到相应的4-酰基-7-甲基-1,2,3,3a，4,8b-六氢环戊[ b ]吲哚-1,2-二醇。在甲酸存在下，在乙腈中用过氧化氢氧化烯丙基双键处的4-酰基-7-甲基-1,3a，4,8b-四氢环戊四烯[ b ]吲哚，得到具有顺式和反式氮原子的立体异构体环氧化物-含和环氧乙烷环。用硝酸铵和三氟乙酸酐的混合物硝化产生5-硝基衍生物。1-（1aR *，1b R *，6b S *，7a S *）-5-甲基-1a，1b，2,6b，7,7ahexahydrooxirenono [4,5] cyclopenta [1,2 - b ]吲哚-2-yl}通过X射线分析确定乙酮。
• 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.
• New synthesis of nitro-substituted 3,1-benzoxazines
  作者：O. A. Andriyanova、D. A. Skladchikov、R. R. Gataullin

  DOI：10.1134/s1070428013060158

  日期：2013.6

  A new one-step procedure has been proposed for the synthesis of nitro derivatives of 3,1-benzoxazines from substituted N-[2-(cyclopent-2-en-1-yl)phenyl]acetamides.