1,4-bis(4-chloro-3,6-dioxocyclohexa-1,4-dienyloxy)-2,5-dichlorobenzene | 136291-79-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,4-bis(4-chloro-3,6-dioxocyclohexa-1,4-dienyloxy)-2,5-dichlorobenzene
• 英文别名: 2-Chloro-5-[2,5-dichloro-4-(4-chloro-3,6-dioxocyclohexa-1,4-dien-1-yl)oxyphenoxy]cyclohexa-2,5-diene-1,4-dione
• CAS: 136291-79-7
• 化学式: C₁₈H₆Cl₄O₆
• 分子量: 460.054
• InChiKey: ORSXWRAEJSNBGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  86.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,5-二氯-1,4-苯醌 在 叔丁基二甲胺 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以35%的产率得到2,5-bis<4-(4-chloro-3,6-dioxocyclohexa-1,4-dienyloxy)-2,5-dichlorophenoxy>benzoquinone
  参考文献：
  名称：

  Novel photoinduced self-substitution of 2,5-dichloro-1,4-benzoquinone

  摘要：

  在阳光照射下，2,5-二氯-1,4-苯醌（DCBQ）在N,N-二甲基叔丁胺（DMBA）或N,N-二甲基-4-苯基双环[2.2.2]辛烷-1-胺（DMPA）的作用下发生自取代反应，生成1,4-双（4-氯-3,6-二氧代环己-1,4-二烯基氧基）-2,5-二氯苯（BDB）和2,5-双[4-(4-氯-3,6-二氧代环己-1,4-二烯基氧基)-2,5-二氯苯氧基]苯醌（BBQ）；光化学诱导的氮化物-氮化物-磷（CIDNP）研究表明，该反应是由DCBQ与胺之间的光诱导电子转移引发，中间体为三重态自由基离子对。

  DOI：

  10.1039/c39910001054

文献信息

• A novel photoinduced self-substitution reaction of dichloro-1,4-benzoquinones in the presence of certain aliphatic tertiary amines
  作者：You-Cheng Liu、Mao-Xi Zhang、Li Yang、Zhong-Li Liu

  DOI：10.1039/p29920001919

  日期：——

  A series of novel compounds has been obtained from the photoinduced self-substitution reactions of 2,5-, 2,6- and 2,3-dichloro-1,4-benzoquinones in the presence of certain hindered N,N-dimethylalkylamines, i.e. N,N-dimethyl-tert-butylamine, N,N-dimethyl-4-phenylbicyclo[2.2.2]-1-octylamine, N,N-dimethyl-1-methylcyclohexylamine, and N,N-dimethylcyclohexylamine. The main products were dimer 4a, trimer 5a and pentamer 6 from 2,5-dichloro-1,4-benzoquinone, dimers 4b and 4c and trimer 5b from 2,6-dichloro-1,4-benzoquinone, and trimer 5c from 2,3-dichloro-1,4-benzoquinone respectively. A mechanism involving photoinduced electron transfer from the amine to the dichlorobenzoquinone (Q) as the initial step is proposed for the reaction on the basis of photo-CIDNP and electrochemical experiments.
• Novel photoinduced self-substitution of 2,5-dichloro-1,4-benzoquinone
  作者：Mao-Xi Zhang、Zhong-Li Liu、Li Yang、You-Cheng Liu

  DOI：10.1039/c39910001054

  日期：——

  2,5-Dichloro-1,4-benzoquinone (DCBQ) undergoes self-substitution to 1,4-bis(4-chloro-3,6-dioxocyclohexa-1,4-dienyloxy)-2,5-dichlorobenzene (BDB) and 2,5-bis[4-(4-chloro-3,6-dioxocyclohexa-1,4-dienyloxy)-2,5-dichlorophenoxy]benzoquinone (BBQ) in the presence of N,N-dimethyl-tert-butylamine (DMBA) or N,N-dimethyl-4-phenylbicyclo[2.2.2]octan-1-ylamine (DMPA) in sunlight; photo-CIDNP studies show that the reaction is initiated by photoinduced electron transfer between DCBQ and the amine with the triplet radical ion pair as the intermediate.

  在阳光照射下，2,5-二氯-1,4-苯醌（DCBQ）在N,N-二甲基叔丁胺（DMBA）或N,N-二甲基-4-苯基双环[2.2.2]辛烷-1-胺（DMPA）的作用下发生自取代反应，生成1,4-双（4-氯-3,6-二氧代环己-1,4-二烯基氧基）-2,5-二氯苯（BDB）和2,5-双[4-(4-氯-3,6-二氧代环己-1,4-二烯基氧基)-2,5-二氯苯氧基]苯醌（BBQ）；光化学诱导的氮化物-氮化物-磷（CIDNP）研究表明，该反应是由DCBQ与胺之间的光诱导电子转移引发，中间体为三重态自由基离子对。