N,N-二(E-2-丁烯基)苯胺 | 59021-43-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: N,N-二(E-2-丁烯基)苯胺
• 英文名称: N,N-di(E-2-butenyl)benzeneamine
• 英文别名: (E)-N,N-di(2-butenyl)aniline；N,N-bis(2-buten-1-yl)aniline；di-but-2-enyl-phenyl-amine；N-phenyldicrotylamine；N,N-bis[(E)-but-2-enyl]aniline
• CAS: 59021-43-1
• 化学式: C₁₄H₁₉N
• 分子量: 201.312
• InChiKey: CQRCVTJBGWSPIR-GGWOSOGESA-N

物化性质

• 沸点：
  292.1±29.0 °C(Predicted)
• 密度：
  0.942±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N-二(E-2-丁烯基)苯胺 在 Co(CO)8 、 一氧化碳 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以53%的产率得到3-乙基-2-丙基-喹啉
  参考文献：
  名称：

  Selective Conversion of Diallylanilines and Arylimines to Quinolines

  摘要：

  A variety of diallylanilines are shown to undergo cobalt-carbonyl catalyzed rearrangement to quinolines. Diallylanilines are also used as allyl transfer reagents to convert benzaldimines into quinolines. Substitution in the 2- and 3-positions of the quinoline is featured in all transformations.

  DOI：

  10.1021/jo026737j
• 作为产物：
  描述：

  2-丁烯基溴 、 叠氮苯 在 tris(dibenzylideneacetone)dipalladium (0) tin(ll) chloride 作用下， 以 二甲基亚砜 为溶剂， 反应 3.17h， 以91%的产率得到N,N-二(E-2-丁烯基)苯胺
  参考文献：
  名称：

  SnCl2 mediated efficient N,N-dialkylation of azides to tertiary-amine via potential stannaimine intermediate

  摘要：

  A base free one-pot conversion of azides to N,N-dialkylamine is described. A two-step reaction pathway has been postulated invoking the intermediacy of stannaimine. This new carbon-nitrogen bond formation strategy adds to the repertoire of tin(II) chemistry. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2005.12.017

文献信息

• Syntheses and Reactions of Allylic and Homoallylic Pyrophosphate Tetraesters
  作者：Yasuo Butsugan、Kenji Nagai、Fumitoshi Nagaya、Hiroki Tabuchi、Katsuhisa Yamada、Shuki Araki

  DOI：10.1246/bcsj.61.1707

  日期：1988.5

  Condensation of alkyl allyl (and 3-methyl-3-butenyl) phosphorochloridates with dialkyl phosphates gave trialkyl allyl (and 3-methyl-3-butenyl) pyrophosphates. Reactions of crotyl (2-butenyl) pyrophosphates with various nucleophiles such as phenolic ethers, aromatic amines, and nitrogen-containing heterocycles in the presence of boron trifluoride etherate gave good to moderate yields of crotylated products. The

  合成了具有烯丙基和高烯丙基侧链的焦磷酸四酯。烷基烯丙基（和 3-甲基-3-丁烯基）磷酰氯与碳酸氢钠反应得到 P1,P2-二烷基 P1,P2-二烯丙基[和 P1,P2-双（3-甲基-3-丁烯基）]焦磷酸。烷基烯丙基（和3-甲基-3-丁烯基）磷酰氯与磷酸二烷基酯的缩合得到三烷基烯丙基（和3-甲基-3-丁烯基）焦磷酸酯。在三氟化硼醚合物存在下，巴豆基（2-丁烯基）焦磷酸酯与各种亲核试剂如酚醚、芳香胺和含氮杂环的反应得到良好至中等产率的巴豆化产物。发现巴豆基焦磷酸酯比相应的正磷酸酯更具反应性。
• Palladium-catalyzed Carbonylation of Allylamines. Synthesis of β,γ-unsaturated amides by one-carbon homologation of Allylamines
  作者：Shun-Ichi Murahashi、Yasushi Imada、Koichi Nishimura

  DOI：10.1016/s0040-4020(01)80767-5

  日期：1994.1

  Palladium-catalyzed carbonylation of allylamines under CO (50atm) at 110°C proceeds highly efficiently to give the corresponding β,γ-unsaturated amides. The carbonylation occurs at the less substituted carbon of allyl units to give linear amides with high regioselectivity. The reaction can be rationalized by assuming the mechanism which involves oxidative addition of palladium (0) species to allylamines

  在110°C的CO（50atm）下钯烯丙基胺的羰基催化羰基化反应非常高效，得到相应的β，γ-不饱和酰胺。羰基化发生在烯丙基单元的较少取代的碳上，得到具有高区域选择性的线性酰胺。可以通过假设以下机理来使反应合理化：该机理涉及将钯（0）物种氧化添加到烯丙胺中以生成π-烯丙基钯络合物，插入一氧化碳以生成酰基戊烯物种和酰胺化。
• Palladium-catalysed carbonylation of allylamines
  作者：Shun-Ichi Murahashi、Yasushi Imada、Koichi Nishimura

  DOI：10.1039/c39880001578

  日期：——

  Carbonylation of allylamines proceeds smoothly in the presence of a palladium–phosphine catalyst to give β,γ-unsaturated amides in good yields.

  在钯-膦催化剂的存在下，烯丙胺的羰基化反应平稳进行，从而以高收率得到β，γ-不饱和酰胺。
• New Experiments in the Reductive N-Alkylation and N-Peralkylation of Aromatic Amines
  作者：G. Verardo、A. G. Giumanini、P. Strazzolini

  DOI：10.1080/00397919408012638

  日期：1994.3

  Some secondary and primary aromatic amines were variously N-alkylated and N-peralkylated by the aldehyde-sodium borohydride procedure in acidic aqueous solution. The procedure lends itself to the alpha-mono and alpha,alpha'-dideuterium labelling of the new N-substituent(s).
• Murahashi Shun-Ichi, Imada Yasushi, Nishimura Koichi, Tetrahedron, 50 (1994) N 2, S 453-464
  作者：Murahashi Shun-Ichi, Imada Yasushi, Nishimura Koichi

  DOI：——

  日期：——