4-bromo-2,3,5-trimethylanisol | 84244-55-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-bromo-2,3,5-trimethylanisol
• 英文别名: 4-Bromo-2,3,5-trimethylanisole；1-bromo-4-methoxy-2,3,6-trimethylbenzene；4-bromo-1-methoxy-2,3,5-trimethylbenzene
• CAS: 84244-55-3
• 化学式: C₁₀H₁₃BrO
• 分子量: 229.117
• InChiKey: MCPVOGPEXPVXBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-bromo-2,3,5-trimethylanisol 在 Ra-Ni palladium diacetate 、 氢氧化钾 、 氢气 、 三溴化磷 、 potassium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， -30.0~25.0 ℃ 、100.0 kPa 条件下， 反应 35.25h， 生成 ethyl (2E,4E.6Z,8Z)-9-(4-methyoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoate
  参考文献：
  名称：

  NeueZugängezu einigen aromatischen Retinoiden

  摘要：

  一些芳香类视黄醇的新方法

  DOI：

  10.1002/hlca.19890720224
• 作为产物：
  描述：

  2,3,5-三甲基苯甲醚 在 吡啶 、 溴 作用下， 以 二氯甲烷 为溶剂， 反应 1.58h， 以93%的产率得到4-bromo-2,3,5-trimethylanisol
  参考文献：
  名称：

  NeueZugängezu einigen aromatischen Retinoiden

  摘要：

  一些芳香类视黄醇的新方法

  DOI：

  10.1002/hlca.19890720224

文献信息

• Novel Phosphinic Acid-Containing Thyromimetics
  申请人：Erion Mark D.

  公开号：US20090028925A1

  公开（公告）日：2009-01-29

  The present invention relates to compounds of phosphonic acid-containing T3 mimetics and monoesters thereof, stereoisomers, pharmaceutically acceptable salts, co-crystals, and prodrugs thereof and pharmaceutically acceptable salts and co-crystals of the prodrugs, as well as their preparation and uses for preventing and/or treating metabolic diseases such as obesity, NASH, hypercholesterolemia and hyperlipidemia, as well as associated conditions such as atherosclerosis, coronary heart disease, impaired glucose tolerance, metabolic syndrome x and diabetes.

  本发明涉及含有磷酸基T3拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟
• Restricted 9-cis retinoids
  申请人：American Cyanamid Company

  公开号：US05968908A1

  公开（公告）日：1999-10-19

  The invention is novel analogs of 9-cis-retinoic acid which are useful for the treatment and prevention of coronary artery disease and to protect against premature atherosclerosis by increasing HDL levels. The invention includes processes for preparing the novel 9-cis-retinoic acid analogs.

  该发明涉及一种新型9-顺-视黄酸类似物，可用于治疗和预防冠状动脉疾病，并通过增加高密度脂蛋白水平来保护免受早期动脉粥样硬化的影响。该发明还包括制备这种新型9-顺-视黄酸类似物的方法。
• Restricted 9-cis-retinoids
  申请人：American Cyanamid Company

  公开号：EP0718285A2

  公开（公告）日：1996-06-26

  The invention is novel analogs of 9-cis-retinoic acid which are useful for the treatment and prevention of coronary artery disease and to protect against premature atherosclerosis by increasing HDL levels. The invention includes processes for preparing the novel 9-cis-retinoic acid analogs.

  本发明是新型 9-顺式维甲酸类似物，可用于治疗和预防冠状动脉疾病，并通过提高高密度脂蛋白水平防止动脉粥样硬化过早发生。本发明包括制备新型 9-顺式维甲酸类似物的工艺。
• Restricted 9-cis retenoids
  申请人：American Cyanamid Company

  公开号：EP0997455A1

  公开（公告）日：2000-05-03

  The invention is novel analogs of 9-cis-retinoic acid which are useful for the treatment and prevention of coronary artery disease and to protect against premature atherosclerosis by increasing HDL levels. The invention includes processes for preparing the novel 9-cis-retinoic acid analogs.

  本发明是新型 9-顺式维甲酸类似物，可用于治疗和预防冠状动脉疾病，并通过提高高密度脂蛋白水平防止动脉粥样硬化过早发生。本发明包括制备新型 9-顺式维甲酸类似物的工艺。
• Nuclear versus Side-Chain Bromination of Methyl-Substituted Anisoles by N-Bromosuccinimide
  作者：Gert-Jan M. Gruter、Otto S. Akkerman、Friedrich Bickelhaupt

  DOI：10.1021/jo00095a023

  日期：1994.8

  The reactions of methyl-substituted anisoles with N-bromosuccinimide in CCl4 are reported. In the absence of a catalyst and under irradiation, some of these substrates undergo nuclear bromination in competition with the well-known side-chain bromination. With 2-methylanisole and with 2,6-dimethylanisole, nuclear bromination is not observed, whereas with 3,5-dimethylanisole, nuclear bromination at the 4-position is the dominating reaction. Investigation of the reactivity of several other methyl-substituted anisoles revealed the following general trend: methyl-substituted anisoles are attacked at the position para to the methoxy group rather than at the side chain when (at least) two methyl groups are present at positions 3 and 5. When positions 2 and 6 are both occupied, nuclear bromination is retarded; in 2,6-dimethylanisole and in 2,3,6-trimethylanisole, only side-chain bromination is observed. In contrast, in 2,3,5,6-tetramethylanisole, the 4-position is sufficiently reactive to be brominated, because the decrease in reactivity by the presence of two methyl groups at positions 2 and 6 is overruled by the two additional methyl groups at positions 3 and 5; as a result, both nuclear and side-chain bromination occur. The observed chemospecificity can be rationalized by a difference in mechanism: the side-chain bromination is a radical reaction, while the nuclear bromination is an electrophilic aromatic substitution reaction, which is so far contrary to expectation, as irradiation had been expected to favor radical processes.