3,3′-diiodo-2,2′-bibenzofuran | 101422-39-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 3,3′-diiodo-2,2′-bibenzofuran
• 英文别名: 3,3'-diiodo-2,2'-bibenzofuran；2,2'-bis-3-iodobenzo[b]furan；3,3'-diiodo-[2,2']bibenzofuranyl；Bis-<3-iod-benzofuranyl-(2)>；3-iodo-2-(3-iodo-1-benzofuran-2-yl)-1-benzofuran
• CAS: 101422-39-3
• 化学式: C₁₆H₈I₂O₂
• 分子量: 486.047
• InChiKey: XCPXZRBYCHYVAW-UHFFFAOYSA-N

物化性质

• 熔点：
  208-211 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6))
• 沸点：
  505.5±50.0 °C(Predicted)
• 密度：
  2.088±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,3′-diiodo-2,2′-bibenzofuran 在 正丁基锂 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.67h， 生成 C₂₂H₁₃O₃P
  参考文献：
  名称：

  Benzofuran-fused Phosphole: Synthesis, Electronic, and Electroluminescence Properties

  摘要：

  A synthetic route to novel benzofuran-fused phosphole derivatives 3-5 is described. These compounds showed optical and electrochemical properties that differ from their benzothiophene analog. Preliminary results show that 4 can be used as an emitter in OLEDs, illustrating the potential of these new compounds for opto-electronic applications.

  DOI：

  10.1021/ol303260d
• 作为产物：
  描述：

  1,4-bis(2-methoxyphenyl)-1,3-butadiyne 在 碘 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以76%的产率得到3,3′-diiodo-2,2′-bibenzofuran
  参考文献：
  名称：

  碘/钯合成多杂环化合物的方法

  摘要：

  报道了一种简单、直接的合成多杂环化合物 (PHC) 的策略，该策略涉及钯催化的 Sonogashira 偶联的迭代循环，然后使用 I 2或 ICl进行碘环化。多种杂环单元，包括苯并呋喃、苯并噻吩、吲哚和异香豆素，可以在温和的反应条件下有效地结合。此外，这种策略的变体提供了各种连接和融合的 PHC。

  DOI：

  10.1021/jo902639f

文献信息

• Iodocyclization of Ethoxyethyl Ethers to Alkynes: A Broadly Applicable Synthesis of 3-Iodobenzo[<i>b</i>]furans
  作者：Takashi Okitsu、Daisuke Nakazawa、Rie Taniguchi、Akimori Wada

  DOI：10.1021/ol8020463

  日期：2008.11.6

  A wide variety of 3-iodobenzo[b]furans were readily prepared by iodocyclization of 2-alkynyl-1-(1-ethoxyethoxy) benzenes with the I(Coll)(2)PF6-BF3 center dot OEt2 combination. Aryl-, vinylic-, and alkyl-substituted alkynes undergo iodocyclization in good to excellent yields. The mechanism of the reaction is also discussed.
• Synthesis and Properties of Benzofuran-Fused Silole and Germole Derivatives: Reversible Dimerization and Crystal Structures of Monomers and Dimers
  作者：Fei-Bao Zhang、Yohei Adachi、Yousuke Ooyama、Joji Ohshita

  DOI：10.1021/acs.organomet.6b00222

  日期：2016.7.25

  Benzofuran-fused silole and germole derivatives were synthesized by the reactions of dilithiobi(benzofuran) with R2SiCl2 and R2GeCl2, respectively. Dilithiobi(benzofuran) was prepared by treating diiodobi(benzofuran) with n-BuLi. Optical and electrochemical measurements of the resulting bis(benzofurano)metalloles and their DFT calculations indicated that the introduction of a metallole unit enhanced the conjugation of bi(benzofuran) mainly by raising the HOMO energy level, similarly to the case of bis(benzothieno)silole prepared previously. Interestingly, [2+2] dimers were obtained by recrystallization of the bis(benzofurano)metalloles, and the dimers readily reverted to the respective monomers upon dissolving in solvent. The crystal structures of the dimers and the monomers were determined by X-ray diffraction studies.