9-iodo-10-(4-methylphenyl)phenanthrene | 725213-56-9

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基萘木脂素
• 英文名称: 9-iodo-10-(4-methylphenyl)phenanthrene
• CAS: 725213-56-9
• 化学式: C₂₁H₁₅I
• 分子量: 394.255
• InChiKey: JPMLMEALPZZOCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.57
• 重原子数：
  22.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  9-iodo-10-(4-methylphenyl)phenanthrene 在 palladium diacetate 、 cesium pivalate 、 双二苯基膦甲烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以56%的产率得到10-methylbenzo[e]acephenanthrylene
  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：

  2-(m-tolylethynyl)-1,1′-biphenyl 在 一氯化碘 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以99%的产率得到9-iodo-10-(4-methylphenyl)phenanthrene
  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

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.