2-叔丁基-4-甲基-5-硝基苯酚 | 103059-08-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 2-叔丁基-4-甲基-5-硝基苯酚
• 英文名称: 2-tert-butyl-4-methyl-5-nitrophenol
• CAS: 103059-08-1
• 化学式: C₁₁H₁₅NO₃
• 分子量: 209.245
• InChiKey: JJEHYIOUADLUIA-UHFFFAOYSA-N

物化性质

• 熔点：
  96-98 °C
• 沸点：
  306.2±42.0 °C(Predicted)
• 密度：
  1.145±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-叔丁基-4-甲基-5-硝基苯酚 在 palladium on activated charcoal 氢气 、 硝酸 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 18.0~25.0 ℃ 、101.33 kPa 条件下， 反应 0.17h， 生成 2,3-diamino-4-hydroxy-5-tert-butyltoluene
  参考文献：
  名称：

  Novel 1H-benzimidazol-4-ols with potent 5-lipoxygenase inhibitory activity

  摘要：

  The synthesis and structure--activity profile of 2-substituted benzimidazol-4-ols as inhibitors of cell-free RBL-1 5-lipoxygenase are discussed, and their potency is compared with that of the standard inhibitors phenidone, AA 861, BW 755C, and nordihydroguaiaretic acid. In contrast to the standard compounds, most did not inhibit the release of slow-reacting substance of anaphylaxis (SRS-A) in vivo when administered at 200 microM ip to rats subjected to peritoneal anaphylaxis, although five compounds containing a methoxylated benzyl group (compounds 36, 39, 42, and 43) or hydroxylated benzyl group (41) showed similar activity to that of phenidone, nordihydroguaiaretic acid, and AA 861. Of the many compounds tested, two, 5-tert-butyl-7-methyl-2-(trifluoromethyl)-1H-benzimidazol-4-ol (57) and 2-(4-methoxybenzyl)-7-methyl-1H-benzimidazol-4-ol (36), like dexamethasone, inhibited monocyte accumulation in a pleural exudate model of inflammation. Standard lipoxygenase inhibitors such as phenidone, BW 755C, and AA 861 were inactive in this system.

  DOI：

  10.1021/jm00395a007
• 作为产物：
  描述：

  2-tert-butyl-4-methy-5-nitrophenyl methanesulfonate 在 sodium hydroxide 作用下， 反应 1.5h， 以74%的产率得到2-叔丁基-4-甲基-5-硝基苯酚
  参考文献：
  名称：

  Novel 1H-benzimidazol-4-ols with potent 5-lipoxygenase inhibitory activity

  摘要：

  The synthesis and structure--activity profile of 2-substituted benzimidazol-4-ols as inhibitors of cell-free RBL-1 5-lipoxygenase are discussed, and their potency is compared with that of the standard inhibitors phenidone, AA 861, BW 755C, and nordihydroguaiaretic acid. In contrast to the standard compounds, most did not inhibit the release of slow-reacting substance of anaphylaxis (SRS-A) in vivo when administered at 200 microM ip to rats subjected to peritoneal anaphylaxis, although five compounds containing a methoxylated benzyl group (compounds 36, 39, 42, and 43) or hydroxylated benzyl group (41) showed similar activity to that of phenidone, nordihydroguaiaretic acid, and AA 861. Of the many compounds tested, two, 5-tert-butyl-7-methyl-2-(trifluoromethyl)-1H-benzimidazol-4-ol (57) and 2-(4-methoxybenzyl)-7-methyl-1H-benzimidazol-4-ol (36), like dexamethasone, inhibited monocyte accumulation in a pleural exudate model of inflammation. Standard lipoxygenase inhibitors such as phenidone, BW 755C, and AA 861 were inactive in this system.

  DOI：

  10.1021/jm00395a007

文献信息

• Benzimidazoles
  申请人：BEECHAM GROUP PLC

  公开号：EP0178413A1

  公开（公告）日：1986-04-23

  Compounds of the general formula I or pharmaceutically acceptable salts or solvates thereof, in which R1 represents hydrogen or a lower alkyl group, R2 represents hydrogen, a lower alkyl group, or R3 represents hydrogen, a lower alkyl group, or R4 represents hydrogen or a lower alkyl group, R5 represents hydrogen or a lower alkyl group, R6 represents hydrogen, a lower alkyl, a substituted or unsubstituted aryl group, or -COOR15, R7 represents hydrogen, halogen or lower alkyl, R8 represents a lower alkyl or a substituted or unsubstituted carbocyclic aryl group, R15 represents hydrogen or a lower alkyl, and n is 0 to 8, n being 0 when R6 represents lower alkyl, are disclosed as an active therapeutic substances for the treatment of inflammatory conditions, allergic conditions and disorders related to loss of gastro-intestinal integrity.

  通式 I 的化合物 或其药学上可接受的盐或溶液，其中 R1 代表氢或低级烷基、 R2 代表氢、低级烷基，或 R3 代表氢、低级烷基，或 R4 代表氢或低级烷基、 R5 代表氢或低级烷基 R6 代表氢、低级烷基、取代或未取代的芳基或-COOR15、 R7 代表氢、卤素或低级烷基、 R8 代表低级烷基或取代或未取代的碳环芳基、 R15 代表氢或低级烷基，以及 n 为 0 至 8，当 R6 代表低级烷基时，n 为 0，这些物质被公开为一种活性治疗物质，用于治疗炎症、过敏症和与胃肠道完整性丧失有关的疾病。
• Derivatives of 2-fluoroalkylbenzimidazole, process for their preparation and pharmaceutical compositions containing them
  申请人：BEECHAM GROUP PLC

  公开号：EP0211489A2

  公开（公告）日：1987-02-25

  A compound of the general formula 1: or a salt or solvate thereof, in which, R' represents hydrogen or a lower alkyl group, R2 represents hydrogen, a lower alkyl group, or R3 represents hydrogen, a lower alkyl group, or R4 represents a lower alkyl group substituted by one or more fluorine atoms, R5 represents hydrogen, halogen or lower alkyl, and R6 represents a lower alkyl or a substituted or unsubstituted carbocyclic aryl group.

  通式 1 的化合物：或其盐或溶液，其中，R'代表氢或低级烷基，R2 代表氢、低级烷基，或 R3 代表氢、低级烷基，或 R4 代表被一个或多个氟原子取代的低级烷基，R5 代表氢、卤素或低级烷基，R6 代表低级烷基或取代或未取代的碳环芳基。
• BUCKLE, DEREK R.;FOSTER, KEITH A.;TAYLOR, JOHN F.;TEDDER, JOHN M.;THODY, +, J. MED. CHEM., 30,(1987) N 12, 2216-2221
  作者：BUCKLE, DEREK R.、FOSTER, KEITH A.、TAYLOR, JOHN F.、TEDDER, JOHN M.、THODY, +

  DOI：——

  日期：——
• US4755525A
  申请人：——

  公开号：US4755525A

  公开（公告）日：1988-07-05
• US4925853A
  申请人：——

  公开号：US4925853A

  公开（公告）日：1990-05-15