2,5-二羟基-2,4,6-环庚并-三烯-1-酮 | 15852-34-3

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物 - 环庚三烯酮
• 中文名称: 2,5-二羟基-2,4,6-环庚并-三烯-1-酮
• 英文名称: 4,5-dihydroxycyclohepta-2,4,6-trien-1-one
• 英文别名: 2,5-dihydroxycyclohepta-2,4,6-trien-1-one；2,5-dihydroxycyclohepta-2,4,6-trienone；5-hydroxy-tropolone；5-Hydroxy-tropolon
• CAS: 15852-34-3
• 化学式: C₇H₆O₃
• 分子量: 138.123
• InChiKey: JVHGZUMMCUZPHC-UHFFFAOYSA-N

物化性质

• 熔点：
  244 °C (decomp)
• 沸点：
  273.5±40.0 °C(Predicted)
• 密度：
  1.525±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.46
• 重原子数：
  10.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.53
• 氢给体数：
  2.0
• 氢受体数：
  3.0

安全信息

• 海关编码：
  2914400090

反应信息

• 作为反应物：
  描述：

  2,5-二羟基-2,4,6-环庚并-三烯-1-酮 在 2,6-二甲基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-methoxy-5-<<(trifluoromethyl)sulfonyl>oxy>tropone
  参考文献：
  名称：

  Keenan, Richard M.; Kruse, Lawrence I., Synthetic Communications, 1989, vol. 19, # 5and6, p. 793 - 798

  摘要：

  DOI：
• 作为产物：
  描述：

  6,7-dioxabicyclo[3.2.2]nona-3,8-dien-2-one 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 2,5-二羟基-2,4,6-环庚并-三烯-1-酮
  参考文献：
  名称：

  Anti-inflammatory activity of 2,5-dihydroxycyclohepta-2,4,6-trienone in rats

  摘要：

  In this study, the anti-inflammatory effects of a tropolone derivative, 2,5-dihydroxycyclohepta-2,4,6-trienone (AD-4), were investigated. The anti-inflammatory potency of AD-4 was compared with that of indomethacin in carrageenan-induced inflammation models in rats. The effect on vascular permeability was also determined by hyaluronidase-induced capillary permeability. AD-4 decreased carrageenan-induced paw edema at doses of 3.62 x 10(2), 7.24 x 10(2), and 14.48 x 10(2) mu mol/kg by 45% (p < 0.001), 79% (p < 0.001), and 83% (p < 0.001), respectively, compared with the value of 49% (p < 0.001) for indomethacin (69.8 mu mol/kg). Additionally, AD-4 decreased hyaluronidase-induced capillary permeability significantly. In conclusion, AD-4 was determined to have anti-inflammatory effects with lower toxicity than indomethacin. Anti-inflammatory effect of AD-4 may be related to its effects on vascular permeability.

  DOI：

  10.1007/s00044-009-9174-z

文献信息

• Preparation of New Liquid Crystals with a Benzoyloxytropone Core
  作者：Akira Mori、Minoru Uchida、Hitoshi Takeshita

  DOI：10.1246/cl.1989.591

  日期：1989.4

  Compounds having liquid crystal properties with a tropolone core were synthesized: A series of 5-alkoxy-2-benzoyloxytropones showed the mesophase(s), whereas corresponding 5-alkoxy-2-benzyloxytropones did not. A [1,9] sigmatropy seems to play an important role to this mesomorphic behavior.

  具有向错酮核的液晶性质化合物合成：一系列5-烷氧基-2-苯甲酰氧基向错酮显示了介晶相，而相应的5-烷氧基-2-苄氧基向错酮则没有。[1,9]σ迁移似乎在这一介晶行为中起重要作用。
• The Thermal Addition Reactions of Cycloheptatriene with Aromatic<i>p</i>-Quinones
  作者：Akira Mori、Hiroaki Mametsuka、Hitoshi Takeshita

  DOI：10.1246/bcsj.58.2072

  日期：1985.7

  Thermal addition reactions of cycloheptatriene with several aromatic p-quinones gave the Diels-Alder adducts as minor products; the most characteristic feature was the formation of the vic-ditropylation products. The mechanism of their formation was clarified to be a sequential ene-reaction and dehydrogenation by means of chemical conversion from the isolated intermediates. Several new other additions

  环庚三烯与几种芳族对醌的热加成反应得到作为次要产物的 Diels-Alder 加合物；最典型的特征是形成vic-ditropylation产物。它们的形成机制被阐明为通过从分离的中间体的化学转化进行的顺序烯反应和脱氢。还注意到了几个新的其他添加，例如连续的 Diels-Alder 反应。
• Synthesis and Electrochemical Properties of 3-(3,6-Dioxo-1,4-cyclohexadienyl)methyl-<i>p</i>-tropoquinone. Analysis of a Four-Electron Redox System by Cyclic Voltammetry
  作者：Akira Mori、Yasutomo Goto、Hitoshi Takeshita

  DOI：10.1246/bcsj.60.2497

  日期：1987.7

  was prepared from 2,5-bis(arylmethoxy)tropone by consecutive reaction, a homolytic rearrangement, subsequent debenzylation, and a DDQ–dehydrogenation. According to cyclic voltammetry, this four-electron redox system was operative, in sharp contrast to the case of the benzenoid bisquinones, via four successive one-electron transfer processes. Two other tropolone derivatives carrying p-benzoquinone segment

  亚甲基连接的双醌，3-(3,6-dioxo-1,4-cyclohexadienyl)methyl-p-tropoquinone，是由 2,5-bis(arylmethoxy)tropone 通过连续反应、均裂重排、随后的脱苄基反应制备的，和DDQ-脱氢。根据循环伏安法，通过四个连续的单电子转移过程，这种四电子氧化还原系统是有效的，与苯类双醌的情况形成鲜明对比。还通过类似的程序制备了另外两种带有对苯醌链段的托酚酮衍生物。这些苯醌的第一还原电位显示出通过分子内氢键的轻微增强。
• Neighboring Effect of a Carbonyl Group in Base-Induced Wittig-Type Rearrangements of Poly(4-nitrobenzyloxy)tropones to Bis- and Mono(α-hydroxy-4-nitrobenzyl)tropones
  作者：Bing Zhu Yin、Akira Mori、Hitoshi Takeshita

  DOI：10.1246/bcsj.64.3306

  日期：1991.11

  The base-catalyzed rearrangement of bis- and tris(4-nitrobenzyloxy)tropones gave (α-hydroxy-4-nitrobenzyl)tropones through a Wittig-type mechanism. Only the 4-nitrobenzyloxy group adjacent to the carbonyl group migrated. The carbonyl group played a role in facilitating the rearrangement by chelation with the sodium on the adjacent carbanion.

  双和三（4-硝基苄氧基）托酮的碱催化重排通过 Wittig 型机制得到（α-羟基-4-硝基苄基）托酮。只有与羰基相邻的 4-硝基苄氧基迁移。羰基通过与相邻碳负离子上的钠螯合，在促进重排方面发挥了作用。
• Synthesis of 3-Arylmethyl-<i>p</i>-tropoquinones from 5-Alkoxy-2-(arylmethoxy)tropones via Homolytic Rearrangement and Oxidation
  作者：Hitoshi Takeshita、Akira Mori、Yasutomo Goto

  DOI：10.1246/bcsj.59.1125

  日期：1986.4

  The 3-(arylmethyl)-p-tropoquinones were synthesized by starting from the homolytic thermal rearrangement of 2-(arylmethoxy)-5-methoxytropones or 2,5-bis(arylmethoxy)tropones, followed by hydrolysis and oxidation. The half-wave potentials of these tropoquinones were determined by cyclic voltammetry. A remote substituent effect was observed for 3-(4-hydroxybenzyl)-p-tropoquinone, which may be attributable

  3-(芳基甲基)-p-tropoquinones 是从 2-(芳基甲氧基)-5-甲氧基托酮或 2,5-双 (芳基甲氧基) 托酮的均裂热重排开始，然后水解和氧化合成的。这些原苯醌的半波电位通过循环伏安法测定。观察到 3-(4-羟基苄基)-p-tropoquinone 的远程取代效应，这可能归因于分子间氢键。