1-bromo-4-(trifluoromethyl)cyclohexane | 30129-20-5

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 英文名称: 1-bromo-4-(trifluoromethyl)cyclohexane
• CAS: 30129-20-5
• 化学式: C₇H₁₀BrF₃
• 分子量: 231.056
• InChiKey: CTEBWBSBKSFIMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-bromo-4-(trifluoromethyl)cyclohexane 在 18-冠醚-6 、 dimethyl sulfide borane 、 potassium carbonate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 N-((6-trifluoromethyl-2-(4-(trifluoromethyl)cyclohexyloxy)pyridin-3-yl)methyl)-2-(3-fluoro-4-(methylsulfonamido)phenyl)propanamide
  参考文献：
  名称：

  2-(3-Fluoro-4-methylsulfonylaminophenyl)propanamides as potent TRPV1 antagonists: Structure activity relationships of the 2-oxy pyridine C-region

  摘要：

  The structure activity relationships of 2-oxy pyridine derivatives in the C-region of N-(6-trifluoromethylpyridin-3-ylmethyl) 2-(3-fluoro-4-methylsulfonylaminophenyl)propanamides as hTRPV1 antagonists were investigated. The analysis indicated that the lipophilicity of the 2-oxy substituents was critical for potent antagonism and 4 or 5 carbons appeared to be optimal for activity. Multiple compounds proved to have comparable activity to 1, which had been reported as the most potent antagonist for capsaicin activity among the previous series of compounds. Further analysis of compounds 22 (2-isobutyloxy) and 53 (2-benzyloxy) in the formalin test in mice demonstrated strong analgesic activity with full efficacy. Docking analysis of 535 using our hTRPV1 homology model indicated that the A- and B-region 2-(3fluoro-4-methylsulfonylaminophenyl)propanamide made important hydrophobic and hydrogen bonding interactions with Tyr511 and that the C-region 6-trifluoromethyl and 2-benzyloxy groups of pyridine occupied the two hydrophobic binding pockets, respectively. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.04.003
• 作为产物：
  描述：

  对三氟甲基苯酚 在 铂 氢气 、 三溴化磷 作用下， 以 溶剂黄146 为溶剂， 生成 1-bromo-4-(trifluoromethyl)cyclohexane
  参考文献：
  名称：

  Blakitnyi,A.N. et al., Journal of Organic Chemistry USSR (English Translation), 1970, vol. 6, # 10, p. 2063 - 2067

  摘要：

  DOI：

文献信息

• [EN] AMIDE COMPOUNDS AS TRYPTOPHAN HYDROXYLASE INHIBITORS<br/>[FR] COMPOSÉS AMIDES UTILISÉS EN TANT QU'INHIBITEURS DE LA TRYPTOPHANE HYDROXYLASE
  申请人：KAROS PHARMACEUTICALS INC

  公开号：WO2016109501A1

  公开（公告）日：2016-07-07

  The present invention is directed to amide compounds which are inhibitors of tryptophan hydroxylase (TPH), particularly isoform 1 (TPH1), that are useful in the treatment or prevention of diseases or disorders associated with peripheral serotonin including, for example, gastrointestinal, cardiovascular, pulmonary, inflammatory, metabolic, fibrotic, and low bone mass diseases, as well as cancer.

  本发明涉及酰胺化合物，这些化合物是色氨酸羟化酶（TPH）的抑制剂，特别是异构体1（TPH1），可用于治疗或预防与外周血清素相关的疾病或紊乱，例如，胃肠道、心血管、肺部、炎症、代谢、纤维化和低骨密度疾病，以及癌症。
• [EN] HETEROCYCLIC COMPOUNDS<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES
  申请人：HOFFMANN LA ROCHE

  公开号：WO2022049134A1

  公开（公告）日：2022-03-10

  The invention provides new heterocyclic compounds having the general formula (I) wherein B, C, L, X, Y, RL and R3 to R5 are as described herein, compositions including the compounds, processes of manufacturing the compounds and methods of using the compounds.

  该发明提供了具有一般式(I)的新杂环化合物，其中B、C、L、X、Y、RL和R3至R5如本文所述，包括这些化合物的组合物、制造这些化合物的方法以及使用这些化合物的方法。
• Deoxytrifluoromethylation of Alcohols
  作者：Nicholas E. Intermaggio、Agustin Millet、Dali L. Davis、David W. C. MacMillan

  DOI：10.1021/jacs.2c04807

  日期：2022.7.13

  Deoxy-functionalization of alcohols represents a class of reactions that has had a profound impact on modern medicine. In particular, deoxyfluorination is commonly employed as a means to incorporate high-value fluorine atoms into drug-like molecules. Recently, the trifluoromethyl (CF3) group has garnered attention from medicinal chemists due to its ability to markedly improve the pharmaceutical properties

  醇的脱氧功能化代表了一类对现代医学产生深远影响的反应。特别是，脱氧氟化作用通常用作将高价值氟原子掺入类药物分子中的一种手段。最近，三氟甲基 (CF 3 ) 基团因其能够显着改善小分子候选药物的药物特性而受到药物化学家的关注。然而，迄今为止，仍然没有实现类似的醇脱氧三氟甲基化的通用方法。我们在此报告了铜金属光氧化还原介导的直接脱氧三氟甲基化，其中醇底物被苯并恶唑盐原位激活，用于 C(sp 3 )–CF 3债券形成。
• 2-(3-Fluoro-4-methylsulfonylaminophenyl)propanamides as potent TRPV1 antagonists: Structure activity relationships of the 2-oxy pyridine C-region
  作者：Shivaji A. Thorat、Dong Wook Kang、HyungChul Ryu、Myeong Seop Kim、Ho Shin Kim、Jihyae Ann、Taehwan Ha、Sung-Eun Kim、Karam Son、Sun Choi、Peter M. Blumberg、Robert Frank、Gregor Bahrenberg、Klaus Schiene、Thomas Christoph、Jeewoo Lee

  DOI：10.1016/j.ejmech.2013.04.003

  日期：2013.6

  The structure activity relationships of 2-oxy pyridine derivatives in the C-region of N-(6-trifluoromethylpyridin-3-ylmethyl) 2-(3-fluoro-4-methylsulfonylaminophenyl)propanamides as hTRPV1 antagonists were investigated. The analysis indicated that the lipophilicity of the 2-oxy substituents was critical for potent antagonism and 4 or 5 carbons appeared to be optimal for activity. Multiple compounds proved to have comparable activity to 1, which had been reported as the most potent antagonist for capsaicin activity among the previous series of compounds. Further analysis of compounds 22 (2-isobutyloxy) and 53 (2-benzyloxy) in the formalin test in mice demonstrated strong analgesic activity with full efficacy. Docking analysis of 535 using our hTRPV1 homology model indicated that the A- and B-region 2-(3fluoro-4-methylsulfonylaminophenyl)propanamide made important hydrophobic and hydrogen bonding interactions with Tyr511 and that the C-region 6-trifluoromethyl and 2-benzyloxy groups of pyridine occupied the two hydrophobic binding pockets, respectively. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Blakitnyi,A.N. et al., Journal of Organic Chemistry USSR (English Translation), 1970, vol. 6, # 10, p. 2063 - 2067
  作者：Blakitnyi,A.N. et al.

  DOI：——

  日期：——