2-溴-5-甲基环己酮 | 89886-68-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-溴-5-甲基环己酮
• 英文名称: 2-bromo-5-methylcyclohexanone
• 英文别名: 2-bromo-5-methyl-cyclohexanone；2-Brom-5-methyl-cyclohexanon；2-bromo-5-methylcyclohexan-1-one
• CAS: 89886-68-0
• 化学式: C₇H₁₁BrO
• 分子量: 191.068
• InChiKey: ZPYHMKMSTCGYAQ-UHFFFAOYSA-N

物化性质

• 熔点：
  83-84 °C
• 沸点：
  103-105 °C(Press: 12 Torr)
• 密度：
  1.391±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-溴-5-甲基环己酮 在 N-氯代丁二酰亚胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 丁酮 为溶剂， 反应 33.0h， 生成
  参考文献：
  名称：

  Discovery of Imidazo[2,1-b]thiazole HCV NS4B Inhibitors Exhibiting Synergistic Effect with Other Direct-Acting Antiviral Agents

  摘要：

  The design, synthesis, and SAR studies of novel inhibitors of HCV NS4B based on the imidazo[2,1-b]thiazole scaffold were described. Optimization of potency with respect to genotype 1b resulted in the discovery of two potent leads 26f (EC50 = 16 nM) and 28g (EC50 = 31 nM). The resistance profile studies revealed that 26f and 28g targeted HCV NS4B, more precisely the second amphipathic alpha helix of NS4B (4BAH2). Cross-resistance between our 4BAH2 inhibitors and other direct-acting antiviral agents targeting NS3/4A, NS5A, and NS5B was not observed. For the first time, the synergism of a series of combinations based on 4BAH2 inhibitors was evaluated. The results demonstrated that our 4BAH2 inhibitor 26f was synergistic with NS3/4A inhibitor simeprevir, NS5A inhibitor daclatasvir, and NS5B inhibitor sofosbuvir, and it could also reduce the dose of these drugs at almost all effect levels. Our study suggested that favorable effects could be achieved by combining 4BAH2 inhibitors such as 26f with these approved drugs and that new all-oral antiviral combinations based on 4BAH2 inhibitors were worth developing to supplement or even replace current treatment regimens for curing HCV infection.

  DOI：

  10.1021/jm501934n
• 作为产物：
  描述：

  3-甲基环己酮 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二甲基亚砜 为溶剂， 反应 0.5h， 生成 2-溴-5-甲基环己酮
  参考文献：
  名称：

  Discovery of Imidazo[2,1-b]thiazole HCV NS4B Inhibitors Exhibiting Synergistic Effect with Other Direct-Acting Antiviral Agents

  摘要：

  The design, synthesis, and SAR studies of novel inhibitors of HCV NS4B based on the imidazo[2,1-b]thiazole scaffold were described. Optimization of potency with respect to genotype 1b resulted in the discovery of two potent leads 26f (EC50 = 16 nM) and 28g (EC50 = 31 nM). The resistance profile studies revealed that 26f and 28g targeted HCV NS4B, more precisely the second amphipathic alpha helix of NS4B (4BAH2). Cross-resistance between our 4BAH2 inhibitors and other direct-acting antiviral agents targeting NS3/4A, NS5A, and NS5B was not observed. For the first time, the synergism of a series of combinations based on 4BAH2 inhibitors was evaluated. The results demonstrated that our 4BAH2 inhibitor 26f was synergistic with NS3/4A inhibitor simeprevir, NS5A inhibitor daclatasvir, and NS5B inhibitor sofosbuvir, and it could also reduce the dose of these drugs at almost all effect levels. Our study suggested that favorable effects could be achieved by combining 4BAH2 inhibitors such as 26f with these approved drugs and that new all-oral antiviral combinations based on 4BAH2 inhibitors were worth developing to supplement or even replace current treatment regimens for curing HCV infection.

  DOI：

  10.1021/jm501934n

文献信息

• Microwave-assisted synthesis of α-hydroxy ketone and α-diketone and pyrazine derivatives from α-halo and α,α′-dibromo ketone
  作者：Takamitsu Utsukihara、Hiroaki Nakamura、Masashige Watanabe、C. Akira Horiuchi

  DOI：10.1016/j.tetlet.2006.10.087

  日期：2006.12

  A novel reaction of α-halo ketone (α-bromo and α-chloro ketone) with irradiation under microwave gave the corresponding α-hydroxyketone and pyrazine derivative in good yields. In the case of α,α′-dibromo ketone, α-diketone was obtained. This reaction affords a new, clean and convenient synthetic method for α-hydroxyketone, α-diketone, α-chloro ketone and pyrazine derivative.

  微波辐射下α-卤代酮（α-溴代和α-氯代酮）的新型反应可得到相应的α-羟基酮和吡嗪衍生物，收率很高。在α，α′-二溴酮的情况下，获得了α-二酮。该反应为α-羟基酮，α-二酮，α-氯酮和吡嗪衍生物的合成提供了一种新的，清洁且方便的方法。
• Halogenation of Carbonyl Compounds by an Ionic Liquid, [AcMIm]X, and Ceric Ammonium Nitrate (CAN)
  作者：Brindaban C. Ranu、Laksmikanta Adak、Subhash Banerjee

  DOI：10.1071/ch07061

  日期：——

  An ionic liquid, acetylmethylimidazolium halide ([AcMIm]X), in combination with ceric ammonium nitrate promotes halogenations of a wide variety of ketones and 1,3-keto esters at the α-position. The ionic liquid acts here as reagent as well as reaction medium, and thus the reaction does not require any organic solvent or conventional halogenating agent. The reaction is completely arrested when the radical

  离子液体乙酰甲基咪唑鎓卤化物 ([AcMIm]X) 与硝酸铈铵结合可促进多种酮和 1,3-酮酯在 α 位的卤化。离子液体在此既充当试剂又充当反应介质，因此该反应不需要任何有机溶剂或常规卤化剂。当使用自由基猝灭剂 TEMPO 时，反应完全停止。还提出了一种似是而非的激进机制。
• Synthesis of 4,6-Dimethyldibenzothiophene and 1,2,3,4-Tetrahydro-4,6-dimethyldibenzothiophene via Tilak Annulation
  作者：Xiaoying Xu、Xiang Li、Anjie Wang、Yinyong Sun、W. Bernd Schweizer、Roel Prins

  DOI：10.1002/hlca.201100191

  日期：2011.10

  1,2,3,4‐Tetrahydro‐4,6‐dimethyldibenzothiophene was prepared by coupling 2‐bromo‐3‐methylcyclohexanone with 2‐methylbenzenethiol and annulating the product with the aid of polyphosphoric acid. A mixture of 1,2,3,4‐tetrahydro‐4,6‐dimethyldibenzothiophene and 4,6‐dimethyldibenzothiophene was prepared by coupling 2‐bromo‐3‐methylcyclohex‐2‐en‐1‐one with 2‐methylbenzenethiol and annulating the product

  1,2,3,4-四氢-4,6-二甲基二苯并噻吩的制备方法是将2-溴-3-3-甲基环己酮与2-甲基苯硫醇偶合，然后借助多磷酸对产物进行环化处理。1,2,3,4-四氢-4,6-二甲基二苯并噻吩和4,6-二甲基二苯并噻吩的混合物是通过将2-溴-3-甲基环己基-2-烯-1-酮与2-甲基苯硫酚偶联并环化而制得的产品借助多磷酸。通过溴化Me 3 Al到Cu-催化的2-Bromocyclohex-2-en-1-one和2-bromo-3-3-methylcyclohex-2-en-1-one中共轭合成Me 3 Al来合成2-Bromo-3-甲基环己酮。消除了3-methylcyclohex-2-en-1-one。1,2,3,4,4a，9b-六氢-4,6-二甲基二苯并噻吩是通过用Zn和CF 3 COOH还原1,2,3,4-四氢-4,6-二甲基二苯并噻吩制备的。
• Transannular Enantioselective (3 + 2) Cycloaddition of Cycloalkenone Hydrazones under Brønsted Acid Catalysis
  作者：Jana Sendra、Efraim Reyes、Liher Prieto、Elena Fernández、Jose L. Vicario

  DOI：10.1021/acs.orglett.1c03190

  日期：2021.11.19

  Hydrazones derived from cycloalkenones undergo an enantioselective transannular formal (3 + 2) cycloaddition catalyzed by a chiral phosphoric acid. The reaction provides high yields and excellent stereocontrol in the formation of complex adducts with one or two α-tertiary amine moieties at the ring fusion, and these can be converted into very versatile stereodefined decalin- or octahydro-1H-indene-derived

  衍生自环烯酮的腙在手性磷酸的催化下发生对映选择性跨环缩甲醛 (3 + 2) 环加成反应。该反应在形成复杂加合物时提供了高产率和出色的立体控制，在环融合处具有一个或两个 α-叔胺部分，这些可以转化为非常通用的立体定义的十氢萘或八氢-1 H-茚衍生的 1， 3-二胺通过简单的还原 N-N 裂解。
• Rh‐Catalyzed Chemodivergent [3+3] Annulations of Diazoenals and α‐Aminoketones: Direct Synthesis of Functionalized 1,2‐Dihydropyridines and Fused 1,4‐Oxazines
  作者：Pratap Kumar Mandal、Sreenivas Katukojvala

  DOI：10.1002/chem.202303862

  日期：2024.4.2

  Chemodivergent [3+3] annulations: The reactivity of Rh-enalcarbenoid has been switched from carbenoid to vinylogous NH-insertion by altering acyclic to cyclic α-amino ketones to deliver functionalized 1,2-dihydropyridines (1,2-DHPs) and fused 1,4-oxazines respectively. The structural diversification of 1,2-DHP and fused 1,4-oxazines gave valuable piperidines, pyrido[1,2-a]indole, 2-pyridone, hexahydroquinolin-2(1H)-ones

  化学发散 [3+3] 环化：通过将无环 α-氨基酮改变为环状 α-氨基酮，Rh-enalcarbenoid 的反应性已从类胡萝卜素转变为插烯 NH-插入，以提供功能化的 1,2-二氢吡啶 (1,2-DHP) 和融合分别为1,4-恶嗪。 1,2-DHP和稠合1,4-恶嗪的结构多样化得到有价值的哌啶、吡啶并[1,2-a]吲哚、2-吡啶酮、六氢喹啉-2( 1H )-酮、六氢喹啉和四氢喹啉酮。