N,N-dimethyl-2-(naphthalen-1-ylethynyl)aniline | 1401560-14-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N,N-dimethyl-2-(naphthalen-1-ylethynyl)aniline
• 英文别名: N,N-dimethyl-2-(2-naphthalen-1-ylethynyl)aniline
• CAS: 1401560-14-2
• 化学式: C₂₀H₁₇N
• 分子量: 271.362
• InChiKey: SEDOYOSTHYDJIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 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-dimethyl-2-(naphthalen-1-ylethynyl)aniline 在 叔丁基过氧化氢 、 copper(l) iodide 、 lithium chloride 、 palladium(II) bromide 作用下， 以 癸烷 、 甲苯 为溶剂， 以76%的产率得到(1-methyl-1H-indol-3-yl)(naphthalen-1-yl)methanone
  参考文献：
  名称：

  钯-铜-共催化的分子内氧化偶联：合成3-acylindoles的有效和原子经济的策略。

  摘要：

  展示了一种新的高效催化方法，可在Pd-Cu共催化的氧化条件下合成3-acylindoles。叔丁基氢过氧化物（TBHP）在该方法中不仅充当氧化剂，而且充当氧气源。该方法允许从容易获得的原料中快速且原子经济地组装3-acylindoles，并能耐受各种官能团。

  DOI：

  10.1039/c2cc37805a
• 作为产物：
  描述：

  邻碘-N,N-二甲基苯胺 在 甲醇 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 三乙胺 作用下， 反应 31.0h， 生成 N,N-dimethyl-2-(naphthalen-1-ylethynyl)aniline
  参考文献：
  名称：

  Pd催化的吲哚化/peri-C-H环化/N-脱烷基化级联到环戊二烯稠合苊[1,2-b]吲哚支架

  摘要：

  已经开发了一种新型 Pd 催化的N , N - 二烷基取代的邻炔基苯胺的级联反应，涉及吲哚化 / peri -C-H 环化 / N -脱烷基化序列，以构建环五稠合苊[1,2- b ]吲哚 (ANI) 支架。多种具有芳香族烃的围在炔末端-C-H键，如萘，菲，芘，荧蒽和，被雇用，得到相应的π扩展ANI衍生物。ANI 分子通过增加 HOMO 和降低 LUMO 显示出相对窄的能隙，这意味着它们在低带隙材料中作为 π 段的潜在应用。

  DOI：

  10.1021/acs.orglett.1c03575

文献信息

• New Access to Six-Membered Phosphacycle Annulated Polyaromatic Ring System
  作者：Erbing Si、Peng Zhao、Lili Wang、Zheng Duan、François Mathey

  DOI：10.1002/ejoc.201901753

  日期：2020.2.14

  A facile access to six‐membered phosphacycle annulated polyaromatic ring system through Ag‐catalyzed intramolecular C–P bond formation reaction, from easily accessible phosphine oxides, has been developed, Several new heteroatoms fused π‐conjugated molecules were synthesized from this procedure with their structures confirmed by X‐ray structure analysis.

  通过易于催化的氧化膦，通过Ag催化的分子内C-P键形成反应，可轻松访问六元磷环环氧基的多芳族环系统。通过该程序合成了几种新的杂原子稠合的π-共轭分子，其结构通过X射线结构分析确认。
• An Efficient Route to 3-Amidylindoles<i>via</i>a Palladium- Catalyzed Tandem Reaction of 2-Alkynylanilines with Isocyanides
  作者：Guanyinsheng Qiu、Chen Chen、Liangqing Yao、Jie Wu

  DOI：10.1002/adsc.201300198

  日期：2013.5.17

  A palladium‐catalyzed reaction of 2‐alkynylaniline, isocyanides, and silver acetate is described, leading to 3‐amidylindoles in moderate to good yields. During the process, five new bonds are formed with high reaction efficiency in one‐pot procedure.

  描述了钯催化的2-炔基苯胺，异氰化物和乙酸银的反应，导致3-酰胺基吲哚的产率中等至良好。在此过程中，通过一锅法形成了五个具有高反应效率的新键。
• Palladium(II)-Catalyzed Tandem Cyclization/C–H Functionalization of Alkynes for the Synthesis of Functionalized Indoles
  作者：Xiao-Feng Xia、Ning Wang、Lu−Lu Zhang、Xian-Rong Song、Xue-Yuan Liu、Yong-Min Liang

  DOI：10.1021/jo301741j

  日期：2012.10.19

  A palladium-catalyzed tandem cyclization/C-H functionalization of two alkynes was accomplished to construct a series of polycyclic functionalized indoles. A range of internal alkynes bearing synthetically useful functional groups were tolerated. A good regioselectivity was observed when alkyl-substituted alkynes were introduced into the reaction system, and a single product was obtained. Molecular oxygen was used as the terminal oxidant in the approach, rendering the reaction more sustainable.
• Application of FeCl3/Diorganyl Diselenides to Cyclization of o-Alkynyl Anilines: Synthesis of 3-Organoselenyl-(N-methyl)indoles
  作者：Gilson Zeni、Adriane Sperança、Benhur Godoi、Paulo Menezes

  DOI：10.1055/s-0033-1338427

  日期：——

  In this manuscript we described the FeCl3/diorganyl diselenides promoted intramolecular cyclization of o-alkynyl anilines, as an alternative for the construction of functionalized 3-organoselenyl indoles. The cyclization reactions proceeded smoothly at room temperature in the presence of air giving the 3-organoselenyl indoles in good yields. Additionally, the 3-organoselenyl indoles proved to be quite useful as synthetic intermediates for the construction of more functionalized indole units through a selenium-lithium exchange reaction followed by trapping the lithium intermediate with different electrophiles.