5-Butyl-4,7-diiodo-1,3-dihydro-isobenzofuran | 903892-49-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 5-Butyl-4,7-diiodo-1,3-dihydro-isobenzofuran
• 英文别名: 5-Butyl-4,7-diiodo-1,3-dihydro-2-benzofuran
• CAS: 903892-49-9
• 化学式: C₁₂H₁₄I₂O
• 分子量: 428.052
• InChiKey: DRKHCOVJJQINDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-Butyl-4,7-diiodo-1,3-dihydro-isobenzofuran 在 甲醇 、 copper(l) iodide 、 1,10-菲罗啉 、 potassium tert-butylate 、 甲酸 、 双氧水 作用下， 以 水 为溶剂， 以56%的产率得到5-Butyl-1,3-dihydro-2-benzofuran-4,7-dione
  参考文献：
  名称：

  Synthesis of 2,5-Dihydrofuran-Fused Quinones from Ether-Tethered Diiododiyne

  摘要：

  Biologically interesting 2,5-dihydrofuran-fused quinones were synthesized via the ruthenium-catalyzed [2 + 2 + 2] cycloaddition of an ether-tethered diiododiyne with alkynes, copper-catalyzed Ullmann coupling of the resultant fused p-diiodobenzenes with methanol or allyl alcohol, and subsequent oxidation of phenol derivatives. The double Claisen rearrangement of the bis(allyl) ether product furnished a diallylhydroquinone derivative, which underwent iron-catalyzed oxidation, ring-closing metathesis, and dehydrogenation to deliver 1,3-dihydronaphtho[2,3-c]furan-4,9-dione.

  DOI：

  10.1021/jo9005975
• 作为产物：
  描述：

  bis(3-iodoprop-2-ynyl)ether 、 1-己炔 在 chloro(1,5-cyclooctadiene)(pentamethylcyclopentadiene)ruthenium(II) 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 4.0h， 以83%的产率得到5-Butyl-4,7-diiodo-1,3-dihydro-isobenzofuran
  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

文献信息

• Synthesis of multiply functionalized benzenes via ruthenium-catalyzed cycloaddition of diiododiynes
  作者：Yoshihiko Yamamoto、Kozo Hattori

  DOI：10.1016/j.tet.2007.09.086

  日期：2008.1

  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.