N-(1,2-dimethylprop-2-en-1-yl)aniline | 145913-61-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(1,2-dimethylprop-2-en-1-yl)aniline
• 英文别名: N-(3-Methylbut-3-en-2-yl)aniline
• CAS: 145913-61-7
• 化学式: C₁₁H₁₅N
• 分子量: 161.247
• InChiKey: MLOKNZRBFAEAIT-UHFFFAOYSA-N

物化性质

• 沸点：
  104 °C(Press: 15 Torr)
• 密度：
  0.947±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(1,2-dimethylprop-2-en-1-yl)aniline 反应 9.0h， 以60%的产率得到2-methyl-2-ethylindoline
  参考文献：
  名称：

  Synthesis of 2-ethyl-2-methyl-2,3-dihydro-1H-indole, a new insecticide exhibiting juvenile hormone activity

  摘要：

  Catalytic hydroamination of isoprene gave N-(1,2-dimethylprop-2-en-1-yl)aniline in a preparative yield. By heating at 260 degrees C the product was converted into 2-ethyl-2-methyl-2,3-dihydro-1H-indole, a new ecologically safe insecticide exhibiting a juvenile hormone activity. Its insecticide properties against Tenebrio Molitor L. chrysalises were estimated at 7.5 points according to the Schmialek 9-point scale.

  DOI：

  10.1134/s107036320612022x
• 作为产物：
  描述：

  苯胺 、 天然橡胶 在 {[P(cyclohexyl)3]2RuCl(CO)(3-methylbut-2-enylidene)}BF₄ 作用下， 以 苯 为溶剂， 反应 36.0h， 生成 N-(3-methylbut-2-enyl)aniline 、 N-(1,2-dimethylprop-2-en-1-yl)aniline
  参考文献：
  名称：

  Ruthenium-Catalyzed Intermolecular Coupling Reactions of Arylamines with Ethylene and 1,3-Dienes:  Mechanistic Insight on Hydroamination vs ortho-C−H Bond Activation

  摘要：

  The cationic ruthenium complex [(PCy3)(2)(CO)(CI)Ru=CHCH=C(CHC3)(2)]+BF4- was found to be an effective catalyst for the coupling reaction of aniline and ethylene to form a similar to 1:1 ratio of N-ethylaniline and 2-methylquinoline products. The analogous reaction with 1,3-dienes resulted in the preferential formation of Markovnikov addition products. The normal isotope effect of k(NH)/k(ND) = 2.2 (aniline and aniline-d(7) at 80 degrees C) and the Hammett p = -0.43 (correlation of para-substituted P-X-C6H4NH2) suggest an N-H bond activation rate-limiting step for the catalytic reaction.

  DOI：

  10.1021/ol050524+

文献信息

• Palladium(II)-catalyzed Amination of Isoprene with Aniline
  作者：E. A. Petrushkina、N. E. Mysova、A. V. Orlinkov

  DOI：10.1007/s11176-005-0344-5

  日期：2005.6

  reaction of isoprene with aniline, catalyzed by the Pd(acac)2-(RO)3P-CF3CO2H system, 1 : 4 : 4 [R = Me, Et; acac = (CH3CO)2CH], in MeCN provides N -(3-methylbut-2-en-1-yl)aniline with a high selectivity (up to 84%) and a nearly quantitative yield (75%). At 1 : 4 : 20 and 1 : 4 : 40 molar component ratios in the catalytic system, up to 28–31% of N,N -(2,3-dimethylprop-2-en-1-yl)aniline is formed. Telomeric

  Pd（acac）2-（RO）3 P-CF 3 CO 2 H系统1：4：4催化异戊二烯与苯胺的反应[R = Me，Et; acac =（CH 3 CO）2 CH]，在MeCN中， N- （3-甲基丁-2-烯-1-基）苯胺具有很高的选择性（高达84％）和接近定量的产率（75％）。在催化体系中，摩尔比为1：4：20和1：4：40时，最多可形成28-31％的 N，N- （2,3-二甲基丙-2-烯-1-基）苯胺。端粒反应产物以1：2：4和1：1：10的比例出现。
• Reaction between isoprene and aniline on complex palladium catalysts
  作者：E. A. Petrushkina、L. I. Zakharkin

  DOI：10.1007/bf00864336

  日期：1992.8

  Isoprene and aniline have been reacted on the catalytic system Pd(acac)2-Ph3P to form a mixture of isomeric telomers: N-(dimethyloctadien-2,7-yl-1)anilines and N-(dimethyloctadien-1,7-yl-3)anilines but on the catalytic system Pd(acac)2-Ph3P-CF3COOH the main product is a mixture of N-(methylbuten-2-yl)aniline adducts. The reaction between N-methylaniline and isoprene on the latter catalyst also gives a mixture of N-methyl and N-(methylbuten-2-yl)aniline adducts.
• ETEMAD-MOGHADAM G.; BENHAMOU M. C.; SPEZIALE V.; LATTES A., NOUV. J. CHIM., 1980, 4, NO 12, 727-730,
  作者：ETEMAD-MOGHADAM G.、 BENHAMOU M. C.、 SPEZIALE V.、 LATTES A.

  DOI：——

  日期：——
• Ruthenium-Catalyzed Intermolecular Coupling Reactions of Arylamines with Ethylene and 1,3-Dienes:  Mechanistic Insight on Hydroamination vs <i>o</i><i>rtho</i>-C−H Bond Activation
  作者：Chae S. Yi、Sang Young Yun

  DOI：10.1021/ol050524+

  日期：2005.5.1

  The cationic ruthenium complex [(PCy3)(2)(CO)(CI)Ru=CHCH=C(CHC3)(2)]+BF4- was found to be an effective catalyst for the coupling reaction of aniline and ethylene to form a similar to 1:1 ratio of N-ethylaniline and 2-methylquinoline products. The analogous reaction with 1,3-dienes resulted in the preferential formation of Markovnikov addition products. The normal isotope effect of k(NH)/k(ND) = 2.2 (aniline and aniline-d(7) at 80 degrees C) and the Hammett p = -0.43 (correlation of para-substituted P-X-C6H4NH2) suggest an N-H bond activation rate-limiting step for the catalytic reaction.
• Synthesis of 2-ethyl-2-methyl-2,3-dihydro-1H-indole, a new insecticide exhibiting juvenile hormone activity
  作者：E. A. Petrushkina、V. N. Kalinin、G. B. Ivanova、V. A. Kheinman

  DOI：10.1134/s107036320612022x

  日期：2006.12

  Catalytic hydroamination of isoprene gave N-(1,2-dimethylprop-2-en-1-yl)aniline in a preparative yield. By heating at 260 degrees C the product was converted into 2-ethyl-2-methyl-2,3-dihydro-1H-indole, a new ecologically safe insecticide exhibiting a juvenile hormone activity. Its insecticide properties against Tenebrio Molitor L. chrysalises were estimated at 7.5 points according to the Schmialek 9-point scale.