2-[2-(phenylethynyl)phenyl]naphthalene | 725213-53-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-[2-(phenylethynyl)phenyl]naphthalene
• 英文别名: 2-[2-(2-Phenylethynyl)phenyl]naphthalene
• CAS: 725213-53-6
• 化学式: C₂₄H₁₆
• 分子量: 304.391
• InChiKey: BKNDYHVMPBNUGQ-UHFFFAOYSA-N

物化性质

• 沸点：
  498.7±24.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  24
• 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：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-[2-(phenylethynyl)phenyl]naphthalene 在 一氯化碘 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以76%的产率得到6-iodo-5-phenylchrysene
  参考文献：
  名称：

  Synthesis of Fused Polycycles by 1,4-Palladium Migration Chemistry

  摘要：

  Novel palladium migration/arylation methodology for the synthesis of complex fused polycycles has been developed, in which one or more sequential Pd-catalyzed intramolecular migration processes involving C-H activation are employed. The chemistry works best with electron-rich aromatics, which is in agreement with the idea that these palladium-catalyzed C-H activation reactions parallel electrophilic aromatic substitution.

  DOI：

  10.1021/jo048788h
• 作为产物：
  描述：

  1-溴-2-苯基乙炔-苯 、 2-萘硼酸 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 6.0h， 以76%的产率得到2-[2-(phenylethynyl)phenyl]naphthalene
  参考文献：
  名称：

  氟代醇-烃双相体系中未活化的炔烃的布朗斯台德酸催化加氢芳基化：菲骨架的构建†

  摘要：

  通过结合布朗斯台德酸催化剂和由1,1,1,3,3,3-六氟丙烷-2-醇（HFIP）和环己烷组成的两相溶剂体系，实现了未活化炔烃的无过渡金属无氢芳基化反应。该方案适用于多种2-炔基联芳基，其可通过6-内-选择性闭环合成取代的菲。双相体系通过适当地将阳离子中间体与中性化合物分离来实现高效的闭环。乙烯基碳正离子中间体在HFIP相中稳定，而底物和产物在环己烷相中分布以抑制分子间副反应。

  DOI：

  10.1039/c9cc04152d

文献信息

• Synthesis of Polycyclic Aromatic Iodides via ICl-Induced Intramolecular Cyclization
  作者：Tuanli Yao、Marino A. Campo、Richard C. Larock

  DOI：10.1021/ol049161o

  日期：2004.8.1

  The reaction of 2-(arylethynyl)biphenyls with ICl at -78 degrees C affords substituted polycyclic aromatic iodides in good to excellent yields. The aryl substituents can be either electron-donating or electron-withdrawing groups such as OMe, Me, CHO, CO(2)Et or NO(2) groups. This chemistry has been successfully extended to systems containing a variety of polycyclic and heterocyclic rings. [reaction:

  2-（芳基乙炔基）联苯与ICl在-78℃下反应以良好或优异的产率提供了取代的多环芳族碘化物。芳基取代基可以是供电子基团或吸电子基团，例如OMe，Me，CHO，CO（2）Et或NO（2）。该化学方法已成功地扩展到包含各种多环和杂环的系统。[反应：看文字]
• Synthesis of Polycyclic Aromatics and Heteroaromatics via Electrophilic Cyclization
  作者：Tuanli Yao、Marino A. Campo、Richard C. Larock

  DOI：10.1021/jo050104y

  日期：2005.4.1

  A variety of substituted polycyclic aromatics are readily prepared in good to excellent yields under very mild reaction conditions by the reaction of 2-(1-alkynyl)biphenyls with ICl, I-2, NBS, and p-O2NC6H4SCl. This methodology readily accommodates various functional groups and has been successfully extended to systems containing a variety of polycyclic and heterocyclic rings.
• Synthesis of Fused Polycycles by 1,4-Palladium Migration Chemistry
  作者：Qinhua Huang、Marino A. Campo、Tuanli Yao、Qingping Tian、Richard C. Larock

  DOI：10.1021/jo048788h

  日期：2004.11.1

  Novel palladium migration/arylation methodology for the synthesis of complex fused polycycles has been developed, in which one or more sequential Pd-catalyzed intramolecular migration processes involving C-H activation are employed. The chemistry works best with electron-rich aromatics, which is in agreement with the idea that these palladium-catalyzed C-H activation reactions parallel electrophilic aromatic substitution.
• Brønsted acid-catalysed hydroarylation of unactivated alkynes in a fluoroalcohol–hydrocarbon biphasic system: construction of phenanthrene frameworks
  作者：Ikko Takahashi、Takeshi Fujita、Noriaki Shoji、Junji Ichikawa

  DOI：10.1039/c9cc04152d

  日期：——

  Transition metal-free hydroarylation of unactivated alkynes was achieved by combining a Brønsted acid catalyst and a two-phase solvent system consisting of 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP) and cyclohexane. This protocol is applicable to a wide variety of 2-alkynylbiaryls which leads to the synthesis of substituted phenanthrenes via 6-endo-selective ring closure. The biphasic system achieves

  通过结合布朗斯台德酸催化剂和由1,1,1,3,3,3-六氟丙烷-2-醇（HFIP）和环己烷组成的两相溶剂体系，实现了未活化炔烃的无过渡金属无氢芳基化反应。该方案适用于多种2-炔基联芳基，其可通过6-内-选择性闭环合成取代的菲。双相体系通过适当地将阳离子中间体与中性化合物分离来实现高效的闭环。乙烯基碳正离子中间体在HFIP相中稳定，而底物和产物在环己烷相中分布以抑制分子间副反应。