2-methoxy-6-(4-p-tolylbuta-1,3-diynyl)naphthalene | 1620636-41-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-methoxy-6-(4-p-tolylbuta-1,3-diynyl)naphthalene
• 英文别名: 2-methoxy-6-(p-tolylbuta-1,3-diyn-1-yl)naphthalene；2-Methoxy-6-[4-(4-methylphenyl)buta-1,3-diynyl]naphthalene
• CAS: 1620636-41-0
• 化学式: C₂₂H₁₆O
• 分子量: 296.368
• InChiKey: QWVVHUGBGWTJDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-乙炔基-6-甲氧基萘 、 4-甲苯基乙炔 在 copper(l) iodide 、 perfluorobutanesulfonyl azide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 氯仿 为溶剂， 反应 0.17h， 以71%的产率得到2-methoxy-6-(4-p-tolylbuta-1,3-diynyl)naphthalene
  参考文献：
  名称：

  Nonafluorobutanesulfonyl Azide as a Shelf-Stable Highly Reactive Oxidant for the Copper-Catalyzed Synthesis of 1,3-Diynes from Terminal Alkynes

  摘要：

  Nonafluorobutanesulfonyl azide is a highly efficient reagent for the copper-catalyzed coupling of terminal alkynes to give symmetrical and unsymmetrical 1,3-diynes in good to excellent yields and with good functional group compatibility. The reaction is extremely fast (<10 min), even at low temperature (-78 degrees C), and requires substoichiometric amounts of a simple copper(I) or copper(II) salt (2-5 mol %) and an organic base (0.6 mol %). A possible mechanistic pathway is briefly discussed on the basis of model DFT theoretical calculations. The quantitative assessment of the safety of use and shelf stability of nonafluorobutanesulfonyl azide has confirmed that this reagent is a superior and safe alternative to other electrophilic azide reagents in use today.

  DOI：

  10.1021/jo5025909

文献信息

• Cu-Catalyzed Fe-Driven C_sp–C_sp and C_sp–C_sp2 Cross-Coupling: An Access to 1,3-Diynes and 1,3-Enynes
  作者：Sabir Ahammed、Debasish Kundu、Brindaban C. Ranu

  DOI：10.1021/jo5011069

  日期：2014.8.15

  An efficient Csp-Csp cross-coupling of alkynyl bromide and pinacol ester of alkynyl boronic acid catalyzed by CuFe2O4 nanoparticles has been accomplished in dimethyl carbonate to produce unsymmetric 1,3-diynes. This protocol is also extended for the Csp-Csp2 coupling of alkynyl bromide and alkenyl boronic acid to provide conjugated 1,3-enynes. The aliphatic, aromatic, and heteroaromatic alkynes couple with various substituted alkynyl/alkenyl boronates/boronic acids by this procedure to furnish a library of 1,3-diynes and enynes in high yields. The catalyst was easily separated by an external magnet and recycled 10 times.