6-bromo-3-methyl-2-naphthol | 1285532-63-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-bromo-3-methyl-2-naphthol
• 英文别名: 6-Bromo-3-methylnaphthalen-2-ol
• CAS: 1285532-63-9
• 化学式: C₁₁H₉BrO
• 分子量: 237.096
• InChiKey: KHVWIYMXNIITJL-UHFFFAOYSA-N

物化性质

• 沸点：
  359.8±22.0 °C(Predicted)
• 密度：
  1.535±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  13
• 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：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-bromo-3-methyl-2-naphthol 在 吡啶 、 咪唑 、 1,1'-双(二苯基膦)二茂铁 、 正丁基锂 、 四丁基氟化铵 、 palladium diacetate 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， -70.0~70.0 ℃ 、101.33 kPa 条件下， 反应 19.16h， 生成 methyl 6-(1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl)-3-methyl-2-naphthoate
  参考文献：
  名称：

  17,20-Lyase inhibitors. Part 4: Design, synthesis and structure–activity relationships of naphthylmethylimidazole derivatives as novel 17,20-lyase inhibitors

  摘要：

  A novel series of naphthylmethylimidazole derivatives and related compounds have been investigated as selective 17,20-lyase inhibitors. Optimization of the substituent at the 6-position on the naphthalene ring was performed to yield a methylcarbamoyl derivative, which exhibited potent inhibitory activity against human 17,20-lyase and promising selectivity (> 200-fold) for 17,20-lyase over CYP3A4. Further modifications of the methylcarbamoyl derivative led to the discovery of the corresponding tricyclic compound, which showed highly potent activity against human 17,20-lyase (IC50 19 nM) and good selectivity (> 1000-fold) for inhibition of 17,20-lyase over CYP3A4. Additional biological evaluation revealed that the tricyclic compound had potent in vivo efficacy in monkeys and favorable pharmacokinetic profiles when administered in rats. Asymmetric synthesis of the selective tricyclic inhibitor was also achieved using a chiral alpha-hydroxy ketone. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.01.017
• 作为产物：
  描述：

  (7-bromo-3-methoxynaphthalen-2-yl)methanol 在 manganese(IV) oxide 、 三溴化硼 、 一水合肼 、 potassium hydroxide 作用下， 以 二氯甲烷 、 三乙二醇 为溶剂， 反应 3.5h， 生成 6-bromo-3-methyl-2-naphthol
  参考文献：
  名称：

  17,20-Lyase inhibitors. Part 4: Design, synthesis and structure–activity relationships of naphthylmethylimidazole derivatives as novel 17,20-lyase inhibitors

  摘要：

  A novel series of naphthylmethylimidazole derivatives and related compounds have been investigated as selective 17,20-lyase inhibitors. Optimization of the substituent at the 6-position on the naphthalene ring was performed to yield a methylcarbamoyl derivative, which exhibited potent inhibitory activity against human 17,20-lyase and promising selectivity (> 200-fold) for 17,20-lyase over CYP3A4. Further modifications of the methylcarbamoyl derivative led to the discovery of the corresponding tricyclic compound, which showed highly potent activity against human 17,20-lyase (IC50 19 nM) and good selectivity (> 1000-fold) for inhibition of 17,20-lyase over CYP3A4. Additional biological evaluation revealed that the tricyclic compound had potent in vivo efficacy in monkeys and favorable pharmacokinetic profiles when administered in rats. Asymmetric synthesis of the selective tricyclic inhibitor was also achieved using a chiral alpha-hydroxy ketone. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.01.017

文献信息

• Inhibitors of factor Xa
  申请人：Millennium Pharmaceuticals, Inc.

  公开号：US20040116399A1

  公开（公告）日：2004-06-17

  Novel compounds, their salts and compositions related thereto having activity against mammalian factor Xa are disclosed. The compounds are useful in vitro or in vivo for preventing or treating coagulation disorders.

  本发明揭示了一种具有对哺乳动物因子Xa活性的新化合物、其盐和相关组合物。这些化合物在体外或体内用于预防或治疗凝血障碍。
• Preparation of hydroxy aromatic carboxylic acids and ester derivatives thereof
  申请人：CELANESE CORPORATION

  公开号：EP0049616A1

  公开（公告）日：1982-04-14

  A process for preparing hydroxy aromatic carboxylic acids, or the ester derivatives thereof, comprises carbonylating a hydroxy aromatic halide in the presence of a reactive alcohol solvent and a catalytic amount of a Group VIII metal catalyst. The process has particular applicability to the preparation of 6-hydroxy-2-naphthoic acid from 6-bromo-2-naphthol, which can be easily prepared from β-naphthol, a readily available and inexpensive starting material.

  制备羟基芳香族羧酸或其酯类衍生物的工艺包括在活性醇溶剂和催化量的第八族金属催化剂存在下对羟基芳香族卤化物进行羰基化。 该工艺特别适用于从 6-溴-2-萘酚制备 6-羟基-2-萘酸，而 6-溴-2-萘酚很容易从β-萘酚制备，β-萘酚是一种容易获得且价格低廉的起始原料。
• US4374262A
  申请人：——

  公开号：US4374262A

  公开（公告）日：1983-02-15