2-(3-methoxypropyn-1-yl)-phenylamine | 142799-06-2

• 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: 2-(3-methoxypropyn-1-yl)-phenylamine
• 英文别名: 2-(3-methoxyprop-1-ynyl)aniline；2-(3-Methoxy-1-propynyl)aniline
• CAS: 142799-06-2
• 化学式: C₁₀H₁₁NO
• 分子量: 161.203
• InChiKey: COEXIWUQQKISAJ-UHFFFAOYSA-N

物化性质

• 沸点：
  279.5±25.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 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：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(3-methoxypropyn-1-yl)-phenylamine 在 吡啶 、 4-二甲氨基吡啶 、 titanium(III) chloride 、 甲烷 、 mercury(II) sulfate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 16.0h， 生成 3-(2-methoxyethyl)-2-(pyridine-2-yl)-indole
  参考文献：
  名称：

  卡那新，吲哚吡咯啉和黄酮哌丁胺的合成

  摘要：

  到植物抗毒素camalexin的短的合成路线7和会聚的方法来生物碱indolopyridocoline 8，6,7- dihydroflavopereirine 15和flavopereirine 9被呈现。从容易获得的前体开始，这些总的合成突出了基于低价钛诱导的氧代酰胺的还原形成C2 lowC3键的吲哚合成新方法的制备潜力。

  DOI：

  10.1016/0040-4020(94)00987-6
• 作为产物：
  描述：

  1-溴-2-硝基苯 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium tetrahydroborate 、 copper(l) iodide 、 二乙胺 、 tin(ll) chloride 作用下， 以 乙醇 为溶剂， 生成 2-(3-methoxypropyn-1-yl)-phenylamine
  参考文献：
  名称：

  Trost, Barry M.; Pedregal, Conchi, Journal of the American Chemical Society, 1992, vol. 114, # 18, p. 7292 - 7294

  摘要：

  DOI：

文献信息

• Cupric Halide-Mediated Intramolecular Halocyclization of N-Electron-Withdrawing Group-Substituted 2-Alkynylanilines for the Synthesis of 3-Haloindoles
  作者：Zengming Shen、Xiyan Lu

  DOI：10.1002/adsc.200900609

  日期：2009.12

  efficient method for the synthesis of 3-haloindoles has been developed. Both 3-chloro- and 3-bromoindole derivatives can be obtained in high yields by the reaction of N-electron-withdrawing group-substituted 2-alkynylanilines with cupric halide in dimethyl sulfoxide (DMSO) within a short period of time. Investigation of the reaction mechanism reveals that two equivalents of cupric halide are necessary

  已经开发了一种方便有效的合成3-卤代吲哚的方法。既3-氯和3-溴吲哚衍生物可以以高产率通过反应而得到Ñ π电子吸引基取代的2- alkynylanilines与卤化铜在短时间内内二甲亚砜（DMSO）。对反应机理的研究表明，需要有两个当量的卤化铜。
• New Access to 2,3-Disubstituted Quinolines through Cyclization of <i>o</i>-Alkynylisocyanobenzenes
  作者：Michinori Suginome、Takeshi Fukuda、Yoshihiko Ito

  DOI：10.1021/ol991133w

  日期：1999.12.1

  [GRAPHICS]o-Alkynylisocyanobenzenes underwent nucleophile-induced intramolecular cyclization to give 2,3-disubstituted quinoline derivatives in high yields. In addition to the oxygen and nitrogen nucleophiles such as methanol and diethylamine, the nucleophilic carbon of the enolate of malonate induced the cyclization effectively. Reaction of 1,4-di(trimethylsilylethynyl)-2,3-diisocyanobenzene with methanol afforded 2,9-dimethoxy-1,10-phenanthroline in good yield.
• Synthesis of 2-Alkoxy(aroxy)-3-substituted Quinolines by DABCO-Promoted Cyclization of <i>o</i>-Alkynylaryl Isocyanides
  作者：Jiaji Zhao、Changlan Peng、Lanying Liu、Yong Wang、Qiang Zhu

  DOI：10.1021/jo1017525

  日期：2010.11.5

  Diversified 2-alkoxy- and 2-aroxy-3-substituted quinolines were synthesized from o-alkynylaryl isocyanides and alcohols and phenols promoted by DABCO, respectively. The reaction was initiated by nucleophilic addition of DABCO to isocyanide and subsequent cycliztion, leading to a DABCO-quinoline-based adduct as the reactive intermediate, followed by substitution of the DABCO moiety with oxygenated nucleophiles.
• Syntheses of camalexin, indolopyridocoline and flavopereirine
  作者：Alois Fürstner、Andreas Ernst

  DOI：10.1016/0040-4020(94)00987-6

  日期：1995.1

  synthetic route to the phytoalexin camalexin 7 and a convergent approach to the alkaloids indolopyridocoline 8, 6,7-dihydroflavopereirine 15 and flavopereirine 9 are presented. Starting from well accessible precursors, these total syntheses highlight the preparative potential of a new method for indole synthesis based on the formation of the C2C3 bond by low-valent titanium induced reductive coupling of oxo-amides

  到植物抗毒素camalexin的短的合成路线7和会聚的方法来生物碱indolopyridocoline 8，6,7- dihydroflavopereirine 15和flavopereirine 9被呈现。从容易获得的前体开始，这些总的合成突出了基于低价钛诱导的氧代酰胺的还原形成C2 lowC3键的吲哚合成新方法的制备潜力。
• Trost, Barry M.; Pedregal, Conchi, Journal of the American Chemical Society, 1992, vol. 114, # 18, p. 7292 - 7294
  作者：Trost, Barry M.、Pedregal, Conchi

  DOI：——

  日期：——