2-Methyl-4-(phenylamino)pent-2-ene | 97206-73-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-Methyl-4-(phenylamino)pent-2-ene
• 英文别名: N-(4-methylpent-3-en-2-yl)aniline
• CAS: 97206-73-0
• 化学式: C₁₂H₁₇N
• 分子量: 175.274
• InChiKey: VPSUSEXHWDKNRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-甲基-1，3-戊二烯 、 苯胺 在 {[P(cyclohexyl)3]2RuCl(CO)(3-methylbut-2-enylidene)}BF₄ 作用下， 以 苯 为溶剂， 反应 36.0h， 以35%的产率得到2-Methyl-4-(phenylamino)pent-2-ene
  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

• Stereospecific addition of singlet phenylnitrenium ion to some alkenes. Reactions of phenyl azide with alkenes in the presence of trifluoroacetic acid
  作者：Hiroshi Takeuchi、Rie Ihara

  DOI：10.1039/c39830000175

  日期：——

  Stereospecific addition to some alkenes of a singlet phenylnitrenium ion, generated from phenyl azide in the presence of trifluoroacetic acid, gives aziridinium ions; this addition is followed by ring-opening reactions of aziridinium ions.

  在三氟乙酸存在下，由叠氮化物苯生成的单线态苯基硝鎓离子立体定向加成到某些烯烃上，得到叠氮鎓离子。该添加之后是叠氮鎓离子的开环反应。
• A novel ring-opening reaction of an aziridinium–AlCl₃complex. Reaction of phenyl azide with alkenes in the presence of AlCl₃
  作者：Hiroshi Takeuchi、Yukihiko Shiobara、Michiharu Mitani、Kikuhiko Koyama

  DOI：10.1039/c39850001251

  日期：——

  Reaction of phenyl azide with alkenes in the presence of AlCl3 gives an aziridinium–AlCl3 complex viaan azide–AlCl3 complex; this reaction is followed by ring-opening reactions of the aziridinium–AlCl3 complex to give N-allylanilines and/or N-phenyl-β-chloroamines after work-up with aqueous Na2CO3, but the reaction with cis-cyclo-octene yields a novel aziridine, 9-phenyl-9-azabicyclo[6.1.0]nonane after the work-up.

  苯肼与烯烃在AlCl3的存在下反应，形成一个通过叠氮化物-AlCl3复合物生成的氮杂环铵-AlCl3复合物；该反应后续会通过氮杂环铵-AlCl3复合物的开环反应生成N-烯丙基苯胺和/或N-苯-β-氯胺，随后用水合Na2CO3处理。然而，与顺式环辛烯的反应在处理后会生成一种新型氮杂环，9-苯基-9-氮杂双环[6.1.0]壬烷。
• Takeuchi, Hiroshi; Koyama, Kikuhiko; Mitani, Michiharu, Journal of the Chemical Society. Perkin transactions I, 1985, p. 677 - 684
  作者：Takeuchi, Hiroshi、Koyama, Kikuhiko、Mitani, Michiharu、Ihara, Rie、Uno, Tomoko、et al.

  DOI：——

  日期：——
• Takeuchi, Hiroshi; Shiobara, Yukihiko; Kawamoto, Hideyuki, Journal of the Chemical Society. Perkin transactions I, 1990, # 2, p. 321 - 327
  作者：Takeuchi, Hiroshi、Shiobara, Yukihiko、Kawamoto, Hideyuki、Koyama, Kikuhiko

  DOI：——

  日期：——
• TAKEUCHI, HIROSHI;IHARA, RIE, J. CHEM. SOC. CHEM. COMMUN., 1983, N 4, 175-177
  作者：TAKEUCHI, HIROSHI、IHARA, RIE

  DOI：——

  日期：——