2-Methyl-1-phenyl-buta-2,3-dienylamine | 138851-78-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-Methyl-1-phenyl-buta-2,3-dienylamine
• CAS: 138851-78-2
• 化学式: C₁₁H₁₃N
• 分子量: 159.231
• InChiKey: HDMJFJCAHZJVIR-UHFFFAOYSA-N

物化性质

• 沸点：
  273.8±20.0 °C(Predicted)
• 密度：
  0.938±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.42
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  26.02
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-Methyl-1-phenyl-buta-2,3-dienylamine 在 三乙胺 、 palladium dichloride 作用下， 以 二氯甲烷 、 N,N-二甲基乙酰胺 为溶剂， 反应 3.0h， 生成 4-allyl-3-methyl-2-phenyl-1-(p-toluenesulfonyl)-2,5-dihydro-1H-pyrrole
  参考文献：
  名称：

  Studies on Pd(II)-Catalyzed Coupling−Cyclization of α- or β-Amino Allenes with Allylic Halides

  摘要：

  The palladium-catalyzed coupling-cyclization of alpha- or beta-amino allenes with allylic halides leading to 3-allylic 2,5-dihydropyrroles and 1,2,3,6-tetrahydropyridines, respectively, was studied. The starting materials are easily available. The skeletons of both two classes of products were established by the X-ray diffraction studies of 7i and 9b. Through the study of the reaction of 2b with 3-chloro-1-butene, 1-chloro-2-butene, and pi-allyl palladium species and the stereochemical outcome of the coupling cyclization of (S)-2m and (R)-2n, it is believed that the current transformation most likely proceeded via a Pd(II)-catalyzed pathway, although a Pd(0) pathway cannot be completely excluded.

  DOI：

  10.1021/jo0342469
• 作为产物：
  描述：

  2-(2-Methyl-1-phenyl-buta-2,3-dienyl)-isoindole-1,3-dione 在 一水合肼 作用下， 以 甲醇 为溶剂， 生成 2-Methyl-1-phenyl-buta-2,3-dienylamine
  参考文献：
  名称：

  Studies on Pd(II)-Catalyzed Coupling−Cyclization of α- or β-Amino Allenes with Allylic Halides

  摘要：

  The palladium-catalyzed coupling-cyclization of alpha- or beta-amino allenes with allylic halides leading to 3-allylic 2,5-dihydropyrroles and 1,2,3,6-tetrahydropyridines, respectively, was studied. The starting materials are easily available. The skeletons of both two classes of products were established by the X-ray diffraction studies of 7i and 9b. Through the study of the reaction of 2b with 3-chloro-1-butene, 1-chloro-2-butene, and pi-allyl palladium species and the stereochemical outcome of the coupling cyclization of (S)-2m and (R)-2n, it is believed that the current transformation most likely proceeded via a Pd(II)-catalyzed pathway, although a Pd(0) pathway cannot be completely excluded.

  DOI：

  10.1021/jo0342469

文献信息

• Synthèse en une étape par voie organométallique d'amines primaries β-acétyléniques α-ramifiées
  作者：L. Leboutet、G. Courtois、L. Miginiac

  DOI：10.1016/0022-328x(91)80258-l

  日期：1991.12

  The one-pot synthesis of alpha-branched beta-alcynyl primary amines results from reaction between organometallic compounds, prepared from propargylic bromides and N-silylimines derived from aromatic or aliphatic aldehydes. Usually, the reaction is regioselective, but not in the case of CH3C = CCH2M.