5-(2,4,6-三甲基苯基)-1,3-环己二酮 | 88311-79-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 5-(2,4,6-三甲基苯基)-1,3-环己二酮
• 中文别名: 5-均三甲苯基-1,3-环己二酮
• 英文名称: 5-(2,4,6-trimethyl-phenyl)-cyclohexane-1,3-dione
• 英文别名: 5-Mesityl-1,3-cyclohexanedione；5-(2,4,6-trimethylphenyl)cyclohexane-1,3-dione
• CAS: 88311-79-9
• 化学式: C₁₅H₁₈O₂
• mdl: MFCD00564144
• 分子量: 230.307
• InChiKey: RGCPDRWZRFMXHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.466
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2914399090

制备方法与用途

用途
5-(2,4,6-三甲基苯基)-1,3-环己二酮是除草剂三甲苯草酮的中间体。

生产方法
其制备方法是将2,4,6-三甲基苯甲醛与丙酮缩合，得到4-(2,4,6-三甲基苯基)-3-丁烯-2-酮，再与丙二酸二甲酯反应。反应生成物经水解、环化和脱羧后，最终得到所需产品。

反应信息

• 作为反应物：
  描述：

  2,3-二氢-2-氧代-1H-苯并咪唑-5-甲醛 、 环戊戊烯酸,Β-氧代,乙酯 、 5-(2,4,6-三甲基苯基)-1,3-环己二酮 在 ammonium acetate 、 1-butyl-3-methylimidazolium Tetrafluoroborate 作用下， 反应 0.17h， 以40%的产率得到2-(2-cyclopentyl-ethyl)-5-oxo-4-(2-oxo-2,3-dihydro-1H-benzimidazol-5-yl)-7-(2,4,6-trimethyl-phenyl)-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  WO2007/51062

  摘要：

  公开号：
• 作为产物：
  描述：

  2,4,6-三甲基苯甲醛 在 sodium ethanolate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 36.0h， 生成 5-(2,4,6-三甲基苯基)-1,3-环己二酮
  参考文献：
  名称：

  Cyclohexane 1,3-diones and their inhibition of mutant SOD1-dependent protein aggregation and toxicity in PC12 cells

  摘要：

  Amyotrophic lateral sclerosis (ALS) is a fatal neurodegenerative disease characterized by the progressive loss of motor neurons. Currently, there is only one FDA-approved treatment for ALS (riluzole), and that drug only extends life, on average, by 2-3 months. Mutations in Cu/Zn superoxide dismutase (SOD1) are found in familial forms of the disease and have played an important role in the study of ALS pathophysiology. On the basis of their activity in a PC12-G93A-YFP high-throughput screening assay, several bioactive compounds have been identified and classified as cyclohexane-1,3-dione (CHD) derivatives. A concise and efficient synthetic route has been developed to provide diverse CHD analogs. The structural modification of the CHD scaffold led to the discovery of a more potent analog (26) with an EC(50) of 700 nM having good pharmacokinetic properties, such as high solubility, low human and mouse metabolic potential, and relatively good plasma stability. It was also found to efficiently penetrate the blood-brain barrier. However, compound 26 did not exhibit any significant life span extension in the ALS mouse model. It was found that, although 26 was active in PC12 cells, it had poor activity in other cell types, including primary cortical neurons, indicating that it can penetrate into the brain, but is not active in neuronal cells, potentially due to poor selective cell penetration. Further structural modification of the CHD scaffold was aimed at improving global cell activity as well as maintaining potency. Two new analogs (71 and 73) were synthesized, which had significantly enhanced cortical neuronal cell permeability, as well as similar potency to that of 26 in the PC12-G93A assay. These CHD analogs are being investigated further as novel therapeutic candidates for ALS. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.039

文献信息

• Cyclohexane-1,3-Diones for Use in the Treatment of Amyotrophic Lateral Sclerosis
  申请人：Kirsch Donald R.

  公开号：US20120264765A1

  公开（公告）日：2012-10-18

  The present invention relates to the identification of provided cyclohexane-1,3-diones (CHD compounds) and pharmaceutical compositions thereof for treating subjects with amyotrophic lateral sclerosis (ALS) and other neurodegenerative diseases. The invention also provides methods of preparing the provided CHD compounds.

  本发明涉及提供的环己烷-1,3-二酮（CHD化合物）的鉴定及其制备的药物组合物，用于治疗患有肌萎缩侧索硬化症（ALS）和其他神经退行性疾病的受试者。本发明还提供了制备所述CHD化合物的方法。
• Substituted dihydropyridines and methods of use
  申请人：Hurt Ray Clarence

  公开号：US20070112015A1

  公开（公告）日：2007-05-17

  Compounds are provided that are modulators of the C5a receptor. The compounds are substituted dihydropyridines and are useful in pharmaceutical compositions, methods for the treatment of diseases and disorders involving the pathologic activtation of C5a receptors.

  提供了调节C5a受体的化合物。这些化合物是取代二氢吡啶，并可用于制药组合物、治疗涉及C5a受体病理性激活的疾病和障碍的方法。
• US8722939B2
  申请人：——

  公开号：US8722939B2

  公开（公告）日：2014-05-13
• US9162968B2
  申请人：——

  公开号：US9162968B2

  公开（公告）日：2015-10-20
• US9593069B2
  申请人：——

  公开号：US9593069B2

  公开（公告）日：2017-03-14