9,9-Bis(3-iodoprop-2-ynyl)fluorene | 903892-32-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9,9-Bis(3-iodoprop-2-ynyl)fluorene
• CAS: 903892-32-0
• 化学式: C₁₉H₁₂I₂
• 分子量: 494.113
• InChiKey: XIWKPFRLOWYRIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 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：

  9,9-Bis(3-iodoprop-2-ynyl)fluorene 、 2-ethynyl-5,5-dimethyl-1,3,2-dioxaborinane 在 chloro(1,5-cyclooctadiene)(pentamethylcyclopentadiene)ruthenium(II) 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 以82%的产率得到2-(4,7-Diiodospiro[1,3-dihydroindene-2,9'-fluorene]-5-yl)-5,5-dimethyl-1,3,2-dioxaborinane
  参考文献：
  名称：

  Synthesis of multiply functionalized benzenes via ruthenium-catalyzed cycloaddition of diiododiynes

  摘要：

  Highly functionalized benzenes were precisely synthesized via multi-step processes consisting of ruthenium-catalyzed [2+2+2] cycloaddition of diiododiynes with an ethynylboronate or terminal alkynes, and subsequent chemo- and regio-selective palladium-catalyzed C-C bond-forming reactions of the resulting cycloadducts. The sequential cycloaddition/coupling process was applied to the synthesis of oligo(p-phenylene ethynylene)s. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.09.086
• 作为产物：
  描述：

  9,9-dipropargylfluorene 在 N-碘代丁二酰亚胺 、 silver nitrate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以75%的产率得到9,9-Bis(3-iodoprop-2-ynyl)fluorene
  参考文献：
  名称：

  Synthesis of Bicyclic p-Diiodobenzenes via Silver-Catalyzed Csp-H Iodination and Ruthenium-Catalyzed Cycloaddition

  摘要：

  Highly substituted iodobenzenes were efficiently and regioselectively synthesized from readily available 1,6-diynes via two-step process consisting of silver-catalyzed Csp-H iodination and subsequent ruthenium-catalyzed [2+2+2] cycloaddition of resultant iododiynes. Some of the obtained iodobenzenes were subjected to palladium-catalyzed C-C bond-forming reactions such as Mizoroki-Heck reaction, Sonogashira reaction, and Suzuki-Miyaura coupling, giving highly conjugated molecules.

  DOI：

  10.1021/ja061619p