2-naphthalen-1-ylethynyl-5-phenyl-oxazole | 1187772-46-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-naphthalen-1-ylethynyl-5-phenyl-oxazole
• 英文别名: 2-(1-naphthylethynyl)-5-phenyloxazole；2-(2-Naphthalen-1-ylethynyl)-5-phenyl-1,3-oxazole；2-(2-naphthalen-1-ylethynyl)-5-phenyl-1,3-oxazole
• CAS: 1187772-46-8
• 化学式: C₂₁H₁₃NO
• 分子量: 295.34
• InChiKey: JSYLOPJTEXTKCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯甲醛 在 copper(I) bromide dimethylsulfide complex 、 potassium carbonate 、 双(2-二苯基磷苯基)醚 、 lithium tert-butoxide 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 1.0h， 生成 2-naphthalen-1-ylethynyl-5-phenyl-oxazole
  参考文献：
  名称：

  Synthesis and evaluation of photophysical properties of Series of π-conjugated oxazole dyes

  摘要：

  Incorporation of pi-conjugated spacers at the 2 or 5 position of a 2,5-disubstitutedaryloxazole led to new series of fluorescent dyes. They show emissions from visible to 700 nm along with significant Stokes shift up to 208 nm and a strong solvatochromic fluorescence. These compounds are easily accessible in one step through direct C-H bond functionalization. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.04.037

文献信息

• Nickel-Catalyzed Direct Alkynylation of Azoles with Alkynyl Bromides
  作者：Naoto Matsuyama、Koji Hirano、Tetsuya Satoh、Masahiro Miura

  DOI：10.1021/ol901684h

  日期：2009.9.17

  The direct C−H alkynylation of azoles with alkynyl bromides proceeds efficiently in the presence of a nickel-based catalyst system. The reaction enables the introduction of various alkynyl groups bearing aryl, alkenyl, alkyl, and silyl substituents to the azole cores. In some cases, addition of a catalytic amount of CuI is observed to accelerate the direct coupling dramatically.

  在镍基催化剂体系的存在下，唑类与炔基溴的直接CH炔基化反应有效进行。该反应能够将带有芳基，烯基，烷基和甲硅烷基取代基的各种炔基引入到唑核中。在某些情况下，观察到添加催化量的CuI可以显着加速直接偶联。
• Copper as a Powerful Catalyst in the Direct Alkynylation of Azoles
  作者：François Besselièvre、Sandrine Piguel

  DOI：10.1002/anie.200904776

  日期：2009.12.7

  Copper‐bottomed catalysis! The direct alkynylation of azoles through a copper‐based CH bond activation, using alkynylbromides as the coupling partner, has been developed (see scheme). The method is very rapid, is functional‐group tolerant, and provides a straightforward entry to diverse alkynyl heterocycles that is complementary to the Sonogashira reaction.

  铜底催化！已经开发了使用炔基溴化物作为偶合伴侣通过基于铜的CH键激活唑的直接炔基化反应（参见方案）。该方法非常快速，具有官能团耐受性，并且可以直接进入与Sonogashira反应互补的各种炔基杂环。
• 1,1-Dibromo-1-alkenes as Valuable Partners in the Copper-Catalyzed Direct Alkynylation of Azoles
  作者：Beatriz Pacheco Berciano、Sabrina Lebrequier、François Besselièvre、Sandrine Piguel

  DOI：10.1021/ol1016433

  日期：2010.9.17

  The copper-catalyzed direct alkynylation of azoles with 1,1-dibromo-1-alkenes as electrophiles is described. These easily accessible substrates are a useful addition to the field of direct alkynylations in an efficient and functional group tolerant reaction to provide a straightforward entry to diverse alkynyl heterocycles.

  描述了铜催化的唑类与1,1-二溴-1-烯烃作为亲电子试剂的直接烷基化反应。这些易于接近的底物是对在有效和官能团耐受的反应中直接炔基化领域有用的添加物，以提供直接进入各种炔基杂环的途径。