2,4,5,7,9,10-Hexamethyl-1,6-dioxapyrene | 135900-96-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,4,5,7,9,10-Hexamethyl-1,6-dioxapyrene
• 英文别名: 3,6,7,10,13,14-Hexamethyl-5,12-dioxatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),6,8,10,13-heptaene
• CAS: 135900-96-8
• 化学式: C₂₀H₂₀O₂
• 分子量: 292.378
• InChiKey: LYLDYAQOUMOIJX-UHFFFAOYSA-N

物化性质

• 沸点：
  427.3±45.0 °C(Predicted)
• 密度：
  1.147±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,5-二羟基萘 在 palladium on activated charcoal 甲醇 、 甲烷磺酸 、 氢气 、 potassium carbonate 、 三乙胺 、 乙酰氯 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.75h， 生成 2,4,5,7,9,10-Hexamethyl-1,6-dioxapyrene
  参考文献：
  名称：

  Synthesis and properties of substituted 1,6-dioxapyrene donors

  摘要：

  The synthesis of substituted 1,6-dioxapyrenes, 2b-g, from 2,6-dipropyl-1,5-naphthalenediol (7a) or 2,6-dimethyl-1,5-naphthalenediol (7b) is described. Diol 7a was prepared by Claisen allylic rearrangement followed by reduction, and 7b was prepared by Mannich reaction of 1,5-naphthalenediol followed by base-promoted hydrogenolysis. The 1,6-dioxapyrenes can be oxidized to stable cation radicals at +0.2-0.35 V vs SCE and to dications at +0.8-1.20 V. The preparation of some tetracyanoquinodimethane salts and binary cation radical salts of the 1,6-dioxapyrenes is reported.

  DOI：

  10.1021/jo00025a020

文献信息

• Bechgaard, Klaus; Lerstrup, Knud; Jorgensen, Mikkel, Molecular Crystals and Liquid Crystals (1969-1991), 1990, vol. 181, p. 161 - 169
  作者：Bechgaard, Klaus、Lerstrup, Knud、Jorgensen, Mikkel、Johannsen, Ib、Christensen, Jorn、Larsen, Jan

  DOI：——

  日期：——
• CHRISTENSEN, J. B.;LARSEN, J.;JOHANNSEN, I.;BECHGAARD, K., SYNTH. METALS, 42,(1991) N, C. 2311-2313
  作者：CHRISTENSEN, J. B.、LARSEN, J.、JOHANNSEN, I.、BECHGAARD, K.

  DOI：——

  日期：——
• Synthesis and properties of substituted 1,6-dioxapyrene donors
  作者：J. B. Christensen、I. Johannsen、K. Bechgaard

  DOI：10.1021/jo00025a020

  日期：1991.12

  The synthesis of substituted 1,6-dioxapyrenes, 2b-g, from 2,6-dipropyl-1,5-naphthalenediol (7a) or 2,6-dimethyl-1,5-naphthalenediol (7b) is described. Diol 7a was prepared by Claisen allylic rearrangement followed by reduction, and 7b was prepared by Mannich reaction of 1,5-naphthalenediol followed by base-promoted hydrogenolysis. The 1,6-dioxapyrenes can be oxidized to stable cation radicals at +0.2-0.35 V vs SCE and to dications at +0.8-1.20 V. The preparation of some tetracyanoquinodimethane salts and binary cation radical salts of the 1,6-dioxapyrenes is reported.