N-(2-甲基亚丙基)-2-苯乙胺 | 85838-87-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(2-甲基亚丙基)-2-苯乙胺
• 英文名称: N-(2-methylpropylidene)-2-phenethylamine
• 英文别名: anti-isobutyraldehyde 2-phenethylimine；N-isobutylidenephenethylamine；N-(2-methylpropylidene)benzeneethanamine
• CAS: 85838-87-5
• 化学式: C₁₂H₁₇N
• 分子量: 175.274
• InChiKey: LQXYVSDRPUTAKA-JLHYYAGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.96
• 重原子数：
  13.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  12.36
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  N-(2-甲基亚丙基)-2-苯乙胺 以73%的产率得到
  参考文献：
  名称：

  Katritzky Alan R., Hong Qingmei, Yang Zhijun, J. Org. Chem., 59 (1994) N 26, S 7947- 7948

  摘要：

  DOI：
• 作为产物：
  描述：

  2-苯乙胺 、 异丁醛 以 甲苯 为溶剂， 反应 17.5h， 以88%的产率得到N-(2-甲基亚丙基)-2-苯乙胺
  参考文献：
  名称：

  Tomaszewski, Miroslaw J.; Warkentin, John; Werstiuk, Nick H., Australian Journal of Chemistry, 1995, vol. 48, # 2, p. 291 - 322

  摘要：

  DOI：

文献信息

• O,O′-Bistributyltin benzopinacolate (1,1,2,2-tetraphenylethane-1,2-bisolate) as thermal source of tributylstannyl radicals
  作者：Mirosław J. Tomaszewski、John Warkentin

  DOI：10.1039/c39930001407

  日期：——

  The previously unknown bistributyltin benzopinacolate was prepared by photolysis of benzophenone in the presence of bistributyltin and used for thermal formation of aryl radicals that undergo subsequent intramolecular addition to an imne bond in an ortho-substituent.

  之前未知的双正丁基锡苯基烯酮通过在双正丁基锡存在下对苯甲酮进行光解而制备，并用于热形成芳基自由基，这些芳基自由基随后在邻位取代基的亚胺键上发生分子内加成反应。
• Addition of alkynyl anions to aldimines containing α-hydrogens: a novel synthesis of β-aminoacetylenes
  作者：Makoto Wada、Yōji Sakurai、Kin-ya Akiba

  DOI：10.1016/s0040-4039(01)80107-6

  日期：1984.1

  Alkynylboranes (or alkynylborates), prepared from lithium acetylide and BF3 · Et2O, added to aldimines containing α-hydrogens to afford β-aminoacetylenes in good yields.

  由乙炔酸锂和BF 3 ·Et 2 O制备的炔基硼烷（或炔基硼酸酯）被添加到含α-氢的醛亚胺中，以高收率得到β-氨基乙炔。
• Addition of boron trifluoride complexes of organocopper reagentsto aldimines containing α-hydrogens
  作者：Makoto Wada、Yōji Sakurai、Kin-ya Akiba

  DOI：10.1016/s0040-4039(01)80106-4

  日期：1984.1

  RCu · BF3, generated in situ from Grignard reagents, CuI, and BF3 · OEt2, added to aldimines containing α-hydrogens to afford secondary amines in good yields. Boron trifluoride complex of dialkylcuprate gave essentially the same result with wider application.

  由Grignard试剂CuI和BF 3 ·OEt 2原位生成的RCu·BF 3加入到含有α氢的醛亚胺中，以高收率得到仲胺。三烷基硼酸酯的三氟化硼配合物在更广泛的应用中获得了基本相同的结果。
• Wada, Makoto; Aiura, Hideki; Akiba, Kin-ya, Heterocycles, 1987, vol. 26, # 4, p. 929 - 934
  作者：Wada, Makoto、Aiura, Hideki、Akiba, Kin-ya

  DOI：——

  日期：——
• Prototype Pictet−Spengler Reactions Catalyzed by Superacids. Involvement of Dicationic Superelectrophiles
  作者：Akihiro Yokoyama、Tomohiko Ohwada、Koichi Shudo

  DOI：10.1021/jo982019e

  日期：1999.1.1

  The Pictet-Spengler reaction, an acid-catalyzed intramolecular cyclization of intermediate imines of 2-arylethylamine to give 1,2,3,4-tetrahydroisoquinolines, has long been limited to active substrates which bear strongly electron-donating groups such as a methoxy or a hydroxy group on the cyclizing benzene ring. in this paper, we present superacid-catalyzed Pictet-Spengler reactions of imines of a-phenethylamine, including the prototype Pictet-Spengler reaction of N-methylene-2-phenethylamine, to give the parent and 1-substituted 1,2,3,4-tetrahydroisoquinolines in moderate to high yields. The yields are dependent on the acidity of the media. A linear relationship was found between the rate of the cyclization and the acidity of the reaction media in kinetic studies of N-methylene-2-phenethylamine and related imines, strongly supporting the intervention of an additional protonative activation of the N-protonated imines, that is, the involvement of dicationic superelectrophiles, N,N-diprotonated imines (ammonium-carbenium dications). We further found that the prototype cyclization of the parent N-methylene-2-phenethylamine is also catalyzed by TFA to give 1,2,3,4-tetrahydroisoquinoline in good yield, although the cyclization is significantly slower than that catalyzed by superacids. The prototype Pictet-Spengler cyclization of N-methylene-2-phenethylamine can thus take place both through the monocation (the N-monoprotonated imine) and the dication (the N,N-diprotonated imine), the latter reaction being predominant in superacids.