9-H-methyl-9H-xanthene-2,7-diol | 170449-36-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 9-H-methyl-9H-xanthene-2,7-diol
• 英文别名: 9-methyl-9H-xanthene-2,7-diol
• CAS: 170449-36-2
• 化学式: C₁₄H₁₂O₃
• 分子量: 228.247
• InChiKey: CBBNJISYXKWWJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3,6-ditertiary butyl-9-methyl-9H-xanthene-2,7-diol 在 三氯化铝 作用下， 以 苯 为溶剂， 反应 2.0h， 以35%的产率得到9-H-methyl-9H-xanthene-2,7-diol
  参考文献：
  名称：

  Comparison of the Efficiencies of the Fused Heterocyclic Compounds, 9H-Xanthene-2,7-diols, and Related Chain-Breaking Phenolic Antioxidants

  摘要：

  The antioxidant activities of 9H-xanthene-2,7-diols that are structurally related to tocopherols and 2,2′-alkylidenedi(hydroquinones) were measured by the inhibition of the thermally initiated autoxidation of tetralin at 60 °C using an oxygen-absorption method. The stoichiometric factors were calculated as n = 3.3—5.5 for 9H-xanthene-2,7-diols and 0.5—0.9 for 2,2′-alkylidenedi(hydroquinones) that lack the fused six-membered heterocyclic ring. Comparison of the alkyl substituent on the bridged methylene carbon showed that 9-methyl-9H-xanthene-2,7-diols increased in n value compared with 9-ethyl-9H-xanthene-2,7-diols. For the 9-methyl-9H-xanthene-2,7-diols, alkyl groups ortho to the phenolic hydroxyl group decreased the Rinh value: two methyl groups by 10-fold, one methyl group by 1.9-fold, and one t-butyl group by 1.4-fold, compared to that for the 9-methyl-9H-xanthene-2,7-diol. On the other hand, 2,2′-alkylidenedi(hydroquinones) were poorer antioxidants than the structurally comparable 9H-xanthene-2,7-diols. The low reactivity of 2,2′-alkylidenedi(hydroquinones) compared to those of 9H-xanthene-2,7-diols is attributed to electronic factors. The p-type lone pair on the hydroxyl oxygen can not help stabilizing the phenoxyl formed upon abstraction of the phenolic hydrogen.

  DOI：

  10.1246/bcsj.69.1713

文献信息

• Polybutadiene composition
  申请人：——

  公开号：US20020032256A1

  公开（公告）日：2002-03-14

  A polybutadiene composition comprising a polybutadiene type polymer and a compound represented by the following formula (I): 1 wherein Ar 1 and Ar 2 each independently represent an aromatic ring, X and Y each independently represent an alkylene group having one or two carbon atoms, an oxygen atom or a carbonyl group, is provided; and thermal degradation of the polybutadiene type polymer can be prevented even in an air-free environment.

  一种聚丁二烯组合物，由聚丁二烯类聚合物和下式(I)所代表的化合物组成： 1 其中 Ar 1 和 Ar 2 分别独立地代表一个芳香环，X 和 Y 分别独立地代表一个或两个碳原子的亚烷基、一个氧原子或一个羰基；即使在无空气环境中，也能防止聚丁二烯型聚合物的热降解。
• US6815481B2
  申请人：——

  公开号：US6815481B2

  公开（公告）日：2004-11-09
• Comparison of the Efficiencies of the Fused Heterocyclic Compounds, 9<i>H</i>-Xanthene-2,7-diols, and Related Chain-Breaking Phenolic Antioxidants
  作者：Tatsuo Yamamura、Takafumi Ishida、Hiroyuki Ueyama、Hirokazu Hayashida、Takuya Ishimaru、Tomihiro Nishiyama

  DOI：10.1246/bcsj.69.1713

  日期：1996.6

  The antioxidant activities of 9H-xanthene-2,7-diols that are structurally related to tocopherols and 2,2′-alkylidenedi(hydroquinones) were measured by the inhibition of the thermally initiated autoxidation of tetralin at 60 °C using an oxygen-absorption method. The stoichiometric factors were calculated as n = 3.3—5.5 for 9H-xanthene-2,7-diols and 0.5—0.9 for 2,2′-alkylidenedi(hydroquinones) that lack the fused six-membered heterocyclic ring. Comparison of the alkyl substituent on the bridged methylene carbon showed that 9-methyl-9H-xanthene-2,7-diols increased in n value compared with 9-ethyl-9H-xanthene-2,7-diols. For the 9-methyl-9H-xanthene-2,7-diols, alkyl groups ortho to the phenolic hydroxyl group decreased the Rinh value: two methyl groups by 10-fold, one methyl group by 1.9-fold, and one t-butyl group by 1.4-fold, compared to that for the 9-methyl-9H-xanthene-2,7-diol. On the other hand, 2,2′-alkylidenedi(hydroquinones) were poorer antioxidants than the structurally comparable 9H-xanthene-2,7-diols. The low reactivity of 2,2′-alkylidenedi(hydroquinones) compared to those of 9H-xanthene-2,7-diols is attributed to electronic factors. The p-type lone pair on the hydroxyl oxygen can not help stabilizing the phenoxyl formed upon abstraction of the phenolic hydrogen.