N-methyl-o-(prop-1-enyl)aniline | 1127329-76-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-methyl-o-(prop-1-enyl)aniline
• 英文别名: 2-(1-propenyl)-N-methylaniline；N-methyl-2-prop-1-enylaniline
• CAS: 1127329-76-3
• 化学式: C₁₀H₁₃N
• mdl: MFCD19218565
• 分子量: 147.22
• InChiKey: INANENBEZXUXFC-UHFFFAOYSA-N

物化性质

• 沸点：
  254.2±19.0 °C(predicted)
• 密度：
  0.982±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 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-methyl-o-(prop-1-enyl)aniline 在 4-二甲氨基吡啶 、 sodium periodate 、 碳酸氢钠 、 N,N'-二环己基碳二亚胺 、 三氟乙酸酐 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 、 丙酮 、 甲苯 为溶剂， 反应 34.5h， 生成 2(1H)-喹啉酮,4-乙烯基-1-甲基-(9CI)
  参考文献：
  名称：

  New entries to 2(1H)-quinolinones and 2H-1-benzazepin-2-ones by acid-catalyzed olefin cyclization of N-(o-(alk-1-enyl)phenyl)-2-(methylsulfinyl)acetamides.

  摘要：

  N-[o-(烯丙基)苯基]-2-(甲基亚砜基)乙酰胺与三氟乙酸酐反应，根据烯烃双键上取代基的位置不同，生成2(1H)-喹啉酮或2H-1-苯并氮杂䓬-2-酮。

  DOI：

  10.1248/cpb.38.3331
• 作为产物：
  描述：

  2-烯丙基-N-甲基苯胺 在 [CpRuCl₂]₂ 、 silver trifluoromethanesulfonate 三苯基膦 作用下， 以 苯 为溶剂， 生成 N-methyl-o-(prop-1-enyl)aniline
  参考文献：
  名称：

  Ruthenium-catalyzed intramolecular cyclization of hetero-functionalized allylbenzenes

  摘要：

  Intramolecular addition of heterofunctionalities to C=C double bonds without P-hydride elimination was investigated and catalyzed by ruthenium complexes. The combination of RuCl3 center dot nH(2)O (10 mol%) and 3 equiv. of AgOTf acted as a catalyst for cyclization of 2-allylphenol (la) to 2,3-dihydro-2-methylbenzofuran (2a) in good yield in the presence of Cu(OTf)(2) as a co-catalyst and PPh3 as a ligand. This catalyst system also catalyzed the cyclization of 2-allylbenzoic acid to lactone in 91% yield. Then, a new catalyst system (RuCp*Cl-2)(2) (1.0 mol%)/4AgOTf/4PPh(3), was found to be more active even in the absence of Cu(OTf)(2). Furthermore, this catalysis was applied to asymmetric reaction of 2-allylphenol (1a). When using To1BINAP as a ligand, over 60% e.e. was achieved. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2006.05.059

文献信息

• Sato, Tatsunori; Ishida, Satoshi; Ishibashi, Hiroyuki, Journal of the Chemical Society. Perkin transactions I, 1991, # 2, p. 353 - 359
  作者：Sato, Tatsunori、Ishida, Satoshi、Ishibashi, Hiroyuki、Ikeda, Masazumi

  DOI：——

  日期：——
• New entries to 2(1H)-quinolinones and 2H-1-benzazepin-2-ones by acid-catalyzed olefin cyclization of N-(o-(alk-1-enyl)phenyl)-2-(methylsulfinyl)acetamides.
  作者：Tatsunori SATO、Tamiko ITO、Hiroyuki ISHIBASHI、Masazumi IKEDA

  DOI：10.1248/cpb.38.3331

  日期：——

  Treatment of N-[o-(alk-1-enyl)phenyl]-2-(methylsulfinyl)acetamides with trifluoroacetic anhydride gave 2(1H)-quinolinones or 2H-1-benzazepin-2-ones, depending upon the position of the substituents on the alkene double bond.

  N-[o-(烯丙基)苯基]-2-(甲基亚砜基)乙酰胺与三氟乙酸酐反应，根据烯烃双键上取代基的位置不同，生成2(1H)-喹啉酮或2H-1-苯并氮杂䓬-2-酮。
• Ruthenium-catalyzed intramolecular cyclization of hetero-functionalized allylbenzenes
  作者：Tetsuo Ohta、Yohei Kataoka、Akio Miyoshi、Yohei Oe、Isao Furukawa、Yoshihiko Ito

  DOI：10.1016/j.jorganchem.2006.05.059

  日期：2007.1

  Intramolecular addition of heterofunctionalities to C=C double bonds without P-hydride elimination was investigated and catalyzed by ruthenium complexes. The combination of RuCl3 center dot nH(2)O (10 mol%) and 3 equiv. of AgOTf acted as a catalyst for cyclization of 2-allylphenol (la) to 2,3-dihydro-2-methylbenzofuran (2a) in good yield in the presence of Cu(OTf)(2) as a co-catalyst and PPh3 as a ligand. This catalyst system also catalyzed the cyclization of 2-allylbenzoic acid to lactone in 91% yield. Then, a new catalyst system (RuCp*Cl-2)(2) (1.0 mol%)/4AgOTf/4PPh(3), was found to be more active even in the absence of Cu(OTf)(2). Furthermore, this catalysis was applied to asymmetric reaction of 2-allylphenol (1a). When using To1BINAP as a ligand, over 60% e.e. was achieved. (c) 2006 Elsevier B.V. All rights reserved.