2,2-Bis(3-iodoprop-2-ynyl)propanedinitrile | 903892-27-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2,2-Bis(3-iodoprop-2-ynyl)propanedinitrile
• CAS: 903892-27-3
• 化学式: C₉H₄I₂N₂
• 分子量: 393.953
• InChiKey: VNKRLWBSFMAQCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2-Bis(3-iodoprop-2-ynyl)propanedinitrile 、 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54%的产率得到
  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：

  diprop-2-ynylmalononitrile 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95%的产率得到2,2-Bis(3-iodoprop-2-ynyl)propanedinitrile
  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