1,5-diacetoxy-2,4-diiodobenzene | 854538-41-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 1,5-diacetoxy-2,4-diiodobenzene
• 英文别名: (5-Acetyloxy-2,4-diiodophenyl) acetate
• CAS: 854538-41-3
• 化学式: C₁₀H₈I₂O₄
• 分子量: 445.98
• InChiKey: SLBLKESMEQXCKP-UHFFFAOYSA-N

物化性质

• 熔点：
  85-86 °C(Solv: ethyl ether (60-29-7); ligroine (8032-32-4))
• 沸点：
  406.2±45.0 °C(Predicted)
• 密度：
  2.135±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,5-diacetoxy-2,4-diiodobenzene 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 bis-triphenylphosphine-palladium(II) chloride lithium hydroxide 、 copper(l) iodide 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 37.33h， 生成 4,6-bis(1'-butylethenyl)-2,8-dihydrobenzo-[1,2-b:5,4-b']dipyran
  参考文献：
  名称：

  An efficient synthesis of fused tricycles with a benzene core via intramolecular double ring-closing enyne metathesis

  摘要：

  A double enyne metathesis reaction has been developed for the efficient synthesis of tricyclic products with a benzene core in good yields. By this protocol, bisannulated benzenes with different ring sizes may he simultaneously constructed from the corresponding precursors in just 'one shot'. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.11.016
• 作为产物：
  描述：

  4,6-diiodoresorcinol 、 乙酸酐 以 吡啶 为溶剂， 以97%的产率得到1,5-diacetoxy-2,4-diiodobenzene
  参考文献：
  名称：

  Highly Conductive Poly(phenylene thienylene)s:  m-Phenylene Linkages Are Not Always Bad

  摘要：

  Two isomeric polymers, which contain meta- or para-phenylene linkages between conducting segments, have been synthesized and compared by electrochemical methods. The nonconjugated poly(1,5-diacetoxy-m-phenylene tetrathienylene) (PMPT-OAc) showed similar electroactivity to the paraisomer, poly(2,5-diacetoxy-p-phenylene tetrathienylene) (PPPT-OAc), in the cyclic voltammetry and in-situ conductivity measurements. Spectroelectrochemistry showed a similar buildup of sub-band-gap electronic transitions. Deacetylation of the polymers was performed successfully by reaction with hydrazine, producing PMPT-OH and PPPT-OH. Both phenol-substituted polymers exhibited greater electroactivity than the acetoxy-substituted polymers. In addition, the phenol substituents were found to lower the "turn-on" potential in the conductivity-potential profile for PMPT-OH, but not for PPPT-OH. An alkoxy-substituted PMPT-OMe shows electroactivity similar to that of PMPT-OAc in the cyclic voltammetry, in-situ conductivity, and spectroelectrochemistry.

  DOI：

  10.1021/ma0501702

文献信息

• Double annulations of dihydroxy- and diacetoxy-dialkynylbenzenes. An efficient construction of benzodifurans
  作者：Zhiqiang Liang、Shengming Ma、Jihong Yu、Ruren Xu

  DOI：10.1016/j.tet.2007.10.051

  日期：2007.12

  An efficient synthetic route to construct disubstituted benzodifurans from dihydroxy- or diacetoxy-dialkynylbenzenes utilizing Cs2CO3 or Pd(OAc)2/Cs2CO3 promoted double annulations is described. The scope for the reaction in the presence of a catalytic amount of Pd(OAc)2 is more general. In addition, it was observed that NaOH-promoted reaction of diacetoxy-dialkynylbenzenes may directly afford in THF/MeOH/H2O

  描述了一种利用Cs 2 CO 3或Pd（OAc）2 / Cs 2 CO 3促进的双环法从二羟基-或二乙酰氧基-二炔基苯构建二取代的苯并呋喃的有效合成途径。在催化量的Pd（OAc）2存在下反应的范围更一般。此外，已观察到，NaOH促进的二乙酰氧基-二炔基苯的反应可以在80°C的苯并二呋喃中以单锅法通过水解和双环化直接在THF / MeOH / H 2 O中提供。但是，在大多数情况下，反应的选择性较低，提供了双环化产物和单环化-水解产物的混合物。
• Palladium-Catalyzed Double Annulations To Construct Multisubstituted Benzodifurans
  作者：Zhiqiang Liang、Shengming Ma、Jihong Yu、Ruren Xu

  DOI：10.1021/jo7016263

  日期：2007.11.1

  Efficient synthetic routes to construct multisubstituted benzo[1,2-b:5,4-b‘]difurans and benzo[1,2-b:4,5-b‘]difurans from bis(allyloxy)bis(alkynyl)benzenes or bis(alkynyl)dihydroxybenzenes and allylic halides utilizing palladium-catalyzed double annulations is reported. By further applying a double ring-closing metathesis reaction, pentacyclic compounds were also prepared.

  有效的合成路线来构建多取代苯并[1,2- b：5,4- b “] difurans和苯并[1,2- b：4,5- b ”]由二difurans（烯丙氧基）双（炔基）苯或据报道，利用钯催化的双环双（炔基）二羟基苯和烯丙基卤化物。通过进一步进行双闭环复分解反应，还制备了五环化合物。