2-(cyclopent-2-en-1-yl)-3,6-dimethylaniline | 108004-66-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-(cyclopent-2-en-1-yl)-3,6-dimethylaniline
• 英文别名: 2-(Cyclopent-2-en-1-yl)-3,6-di-methylaniline；2-cyclopent-2-en-1-yl-3,6-dimethylaniline
• CAS: 108004-66-6
• 化学式: C₁₃H₁₇N
• 分子量: 187.285
• InChiKey: FXOXKDFZFQHEDV-UHFFFAOYSA-N

物化性质

• 沸点：
  142-145 °C(Press: 3 Torr)
• 密度：
  1.034±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(cyclopent-2-en-1-yl)-3,6-dimethylaniline 在 碘 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 N-acetyl-3-iodo-5,8-dimethyl-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole
  参考文献：
  名称：

  A new pathway of the reaction of N-acetyl-2-(2-cyclopenten-1-yl)anilines with iodine

  摘要：

  DOI：

  10.1134/s1070363207040275
• 作为产物：
  描述：

  2,5-二甲基苯胺 、 3-碘苄胺 以79%的产率得到2-(cyclopent-2-en-1-yl)-3,6-dimethylaniline
  参考文献：
  名称：

  Interaction of 2,6- and 2,5-disubstituted aromatic amines with secondary ?-chloroalkenes

  摘要：

  DOI：

  10.1007/bf00956608

文献信息

• 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.
• ABDRAXMANOV, I. B.;SHABAEVA, G. B.;NIGMATULLIN, N. G.;TOLSTIKOV, G. A., IZV. AN CCCP. CEP. XIM., 1986, N 6, 1372-1378
  作者：ABDRAXMANOV, I. B.、SHABAEVA, G. B.、NIGMATULLIN, N. G.、TOLSTIKOV, G. A.

  DOI：——

  日期：——
• Reactions of N- and C-alkenylanilines: VIII. Synthesis of functionalized cycloalka[b]indoles from o-(cycloalk-2-en-1-yl)anilines
  作者：R. R. Gataullin、N. A. Likhacheva、K. Yu. Suponitskii、I. B. Abdrakhmanov

  DOI：10.1134/s1070428007090096

  日期：2007.9

  N-Acyl-2-(cyclohex-2-en-1-yl)anilines react with molecular iodine to give the corresponding N-acyl-1-iodo-1,2,3,4,4a,9a-hexahydrocarbazoles which undergo isomerization into 1-R-2a,3.4,5,5a.10a-hexahydro[1,3]oxazolo[5,4,3-j,k]carbazol-10-ium iodides; no isomerization occurs with N-acetyl-3-iodo-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole. The reaction of N-p-tolylsulfonyl-3,4,4a,9a-tetrahydrocarbazoles with hydrogen peroxide leads to the formation of a single 1,2-epoxy derivative with trans orientation of the nitrogen- and oxygen-containing rings. N-p-Tolylsulfonyl-1,3a,4,8b-tetrahydrocyclopenta[b]lndoles give rise to the corresponding 2,3-epoxy derivatives with both trans and cis orientation of the dihydropyrrole and oxirane fragments. The resulting epoxides undergo trans-opening with formation of N-p-tolylsulfonyl-1- hydroxy-2-methoxy-1,2,3,4,4a,9a-hexahydrocarbazoics and N-p-tolysulfonyl-3-hydroxy-2-methoxy- 1,2,3,3a,4,8b-hexahydrocyclopenta[b]indoles on heating in methanol in the presence of KU-2 cation exchanger. Mutual orientation of the oxirane and nitro-en-containina rin-s in the epoxides derived from cyclopenta[b]indoles was proved by X-ray analysis.