2,3-Dibromo-6-methyl-[1,4]naphthoquinone | 72364-92-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,3-Dibromo-6-methyl-[1,4]naphthoquinone
• 英文别名: 2,3-Dibromo-1,4-dihydro-1,4-dioxo-6-methylnaphthalene；2,3-dibromo-6-methylnaphthalene-1,4-dione
• CAS: 72364-92-2
• 化学式: C₁₁H₆Br₂O₂
• 分子量: 329.975
• InChiKey: LEMOZHOQBADFFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-Dibromo-6-methyl-[1,4]naphthoquinone 在 氨 作用下， 以 硝基苯 为溶剂， 反应 0.5h， 以75%的产率得到2-Amino-3-bromo-6-methyl-[1,4]naphthoquinone
  参考文献：
  名称：

  Studies on v-triazoles. 9. Antiallergic 4,9-dihydro-4,9-dioxo-1H-naphtho[2,3-d]-v-triazoles

  摘要：

  A short series of the title compounds was prepared and evaluated for antiallergic activity in the rat passive cutaneous anaphylaxis screen. All but the two N-methylated derivatives were active in this screen by the intravenous route, the most potent being the symmetrical dimethyl compound, 4,9-dihydro-6,7-dimethyl-4,9-dioxo-1H-naphtho[2,3-d]-v-triazole, and its 5-nitro derivative. The latter two compounds were noticeably more potent than disodium cromoglycate, and one of these, the unnitrated material, was selected for further evaluation as a potential antiasthmatic drug.

  DOI：

  10.1021/jm00359a016
• 作为产物：
  描述：

  6-甲基-1,4-萘醌 在 溴 作用下， 以 二氯甲烷 为溶剂， 以69%的产率得到2,3-Dibromo-6-methyl-[1,4]naphthoquinone
  参考文献：
  名称：

  Studies on v-triazoles. 9. Antiallergic 4,9-dihydro-4,9-dioxo-1H-naphtho[2,3-d]-v-triazoles

  摘要：

  A short series of the title compounds was prepared and evaluated for antiallergic activity in the rat passive cutaneous anaphylaxis screen. All but the two N-methylated derivatives were active in this screen by the intravenous route, the most potent being the symmetrical dimethyl compound, 4,9-dihydro-6,7-dimethyl-4,9-dioxo-1H-naphtho[2,3-d]-v-triazole, and its 5-nitro derivative. The latter two compounds were noticeably more potent than disodium cromoglycate, and one of these, the unnitrated material, was selected for further evaluation as a potential antiasthmatic drug.

  DOI：

  10.1021/jm00359a016
• 作为试剂：
  描述：

  2-氨基吡啶 、 2,3-Dibromo-6-methyl-[1,4]naphthoquinone 、 乙醇 在 乙醇 、 2,3-Dibromo-6-methyl-[1,4]naphthoquinone 、 methylene chloride-heptane 、 raw product 、 silica 、 N-乙酰基-S-法呢基-L-半胱氨酸 、 methanol-dichloromethane 、 ethyl acetate heptane 作用下， 反应 48.0h， 以to produce 6,11-dihydro-6,11-dioxo-8-methylnaphtho[2,,3':4,5]imidazo[1,2-a]pyridine, 6,11-dihydro-6,11-dioxo-9-methylnaphtho[2',3':4,5]imidazo[1,2-a] pyridine, 5,6-dihydro-5,6-dioxo-2-methylnaphtho[1',2':4,5] imidazo[1,2-a]pyridine or 5,6-dihydro-5,6-dioxo-3-methylnaphth [1',2':4,5]imidazo[1,2-a]pyridine in the form of orange crystals的产率得到
  参考文献：
  名称：

  Mono-- or diketone tetracyclic derivatives and therapeutical uses thereof

  摘要：

  关于四环类衍生物的治疗用途及其药学上可接受的盐的发明，其具有以下通式：##STR1## 其中，独立于其他：X是碳或氮原子，T是碳或氮原子，L是氧原子或酮基保护基团，R.sub.1是氢原子、卤素原子或C.sub.1至C.sub.5烷基基团，R.sub.2是氢原子、卤素原子、硝基基团或C.sub.1至C.sub.5烷基基团，n和m等于0或1，但不能独立于其他，因此如果n等于1，则m等于0，如果n等于0，则m等于1。

  公开号：

  US05981544A1

文献信息

• BUCKLE, D. R.;SMITH, H.;SPICER, B. A.;TEDDER, J. M., J. MED. CHEM., 1983, 26, N 5, 714-719
  作者：BUCKLE, D. R.、SMITH, H.、SPICER, B. A.、TEDDER, J. M.

  DOI：——

  日期：——
• 4,9-Dihydro-4,9-dioxo-1H-naphtho(2,3-d) triazoles, their preparation and antiallergic compositions containing them
  申请人：BEECHAM GROUP PLC

  公开号：EP0002310B1

  公开（公告）日：1981-06-24
• US4263309A
  申请人：——

  公开号：US4263309A

  公开（公告）日：1981-04-21
• US5981544A
  申请人：——

  公开号：US5981544A

  公开（公告）日：1999-11-09
• Studies on v-triazoles. 9. Antiallergic 4,9-dihydro-4,9-dioxo-1H-naphtho[2,3-d]-v-triazoles
  作者：Derek R. Buckle、Harry Smith、Barbara A. Spicer、John Martin Tedder

  DOI：10.1021/jm00359a016

  日期：1983.5

  A short series of the title compounds was prepared and evaluated for antiallergic activity in the rat passive cutaneous anaphylaxis screen. All but the two N-methylated derivatives were active in this screen by the intravenous route, the most potent being the symmetrical dimethyl compound, 4,9-dihydro-6,7-dimethyl-4,9-dioxo-1H-naphtho[2,3-d]-v-triazole, and its 5-nitro derivative. The latter two compounds were noticeably more potent than disodium cromoglycate, and one of these, the unnitrated material, was selected for further evaluation as a potential antiasthmatic drug.