6-dimethylamino-4-phenyl-4-[4]pyridyl-hexan-3-one | 109865-60-3

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 6-dimethylamino-4-phenyl-4-[4]pyridyl-hexan-3-one
• 英文别名: 6-Dimethylamino-4-phenyl-4-[4]pyridyl-hexan-3-on
• CAS: 109865-60-3
• 化学式: C₁₉H₂₄N₂O
• 分子量: 296.412
• InChiKey: YAKNXMUQOXOZIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  33.2
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  丙酰氯 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium amide 、 甲苯 作用下， 生成 6-dimethylamino-4-phenyl-4-[4]pyridyl-hexan-3-one
  参考文献：
  名称：

  US2774768

  摘要：

  公开号：

文献信息

• Basic ketones and a process of preparing them
  申请人：HOECHST AG

  公开号：US02731462A1

  公开（公告）日：1956-01-17

  The invention comprises basic ketones of the formula <;FORM:0719237/IV (b)/1>; p in which R1 and R2 each represent an alkyl radical having up to 6 carbon atoms or together represent a four- or five-membered divalent residue, R3 represents a methylene group or a methylene group containing as a substituent an alkyl radical having up to 6 carbon atoms, R4 represents the residue of pyridine, thiazole or pyrimidine a ring carbon atom of which is directly bound to the central C-atom, R5 represents a phenyl, hydroxy-phenyl or alkoxy-phenyl radical and R7 represents an alkyl radical containing up to 6 carbon atoms, and salts of such basic ketones. Such compounds are obtained by reacting a carboxylic acid ester of the formula <;FORM:0719237/IV (b)/2>; with an alkyl magnesium halide, and, if desired, converting the free base so obtained into a salt. The carboxylic acid esters are produced by reacting an ester of the formula R4R5CH.COO.Alkyl with a basically substituted alkyl halide. Better yields are generally obtained when "Alkyl" in the ester is a branched alkyl radical. Salts of the above compounds mentioned are those with sulphuric, hydrochloric, phosphoric, acetic, propionic, benzoic and ethane sulphonic acids, and (for identification purposes) the succinic and maleic acid salts. In an example: (1) a - phenyl - a - pyridyl - (2) - g - N - pyrrolidino-butyric acid ethyl ester (prepared by reacting phenyl-pyridyl-(2)-acetic acid ethyl ester and N-b -chlorethyl-pyrrolidine in the presence of sodamide) is reacted with ethyl magnesium bromide to give 1-N-pyrrolidino-3-phenyl-3-pyridyl-(2)-hexanone, which is converted to its succinate. Similarly prepared are (2) 1 - dimethylamino - 3 - phenyl - 3 - pyridyl - (21) - hexanone - (4) from a - phenyl - a - pyridyl - (2) - g - dimethylamino - butyric acid ethyl ester; (3) 1-N-morpholino-3-phenyl-3-pyridyl-(21)-hexanone-(4) from a -phenyl-a -pyridyl-(2)-g -N-morpholino-butyric acid ethyl or isopropyl ester; (4) an isomeric mixture of 2-dimethylamino-4-phenyl-4-pyridyl-(21)-heptanone-(5) and 1 - dimethylamino - 2 - methyl - 3 - phenyl - 3-pyridyl-(21)-hexanone-(4) from an isomeric mixture of a -phenyl-a -pyridyl-(2)-g -dimethylamino-valeric acid and a -phenyl-a -pyridyl-(2)-b - methyl - g - dimethylamino - butyric acid ethyl ester; (5) 1-dimethylamino-3-phenyl-3-pyridyl - (41) - hexanone - (4) from phenyl - pyridyl-(4)-acetic acid ethyl ester; (6) 1-dimethylamino - 3 - phenyl - 3 - thiazolyl - (21) - hexanone-(4) from a -phenyl-a -thiazolyl-(2)-g -dimethylamino-butyric acid ethyl ester; (7) 1-N - pyrrolidino - 3 - phenyl - 3 - thiazolyl - (21) - hexanone-(4) from a -phenyl-a -thiazolyl-(2)-g -N-pyrrolidino-butyric acid methyl ester; (8) 1 - N - piperidino - 3 - phenyl - 3 - thiazolyl - (21) - hexanone - (4) from a - phenyl - a - thiazolyl - (2) - g - N - piperidino - butyric acid methyl ester; (9) 1-N-morpholino-3-phenyl-3-thiazolyl-(21)-hexanone-(4) from a -phenyl-a -thiazolyl-(2)-g -N-morpholino-butyric acid methyl ester; (10) 1 - diethylamino - 3 - phenyl - 3 - thiazolyl-(21) - hexanone - (4) from a - phenyl - a - thiazolyl - (2) - g - diethylamino - butyric acid ethyl ester; (11) 1-dimethylamino-3-(31-methoxy - phenyl) - 3 - thiazolyl - (21) - hexanone - (4) from a - (31 - methoxy - phenyl) - a - thiazolyl - (21) - g - dimethylamino - butyric acid methyl ester. The product is converted to the corresponding 31-hydroxy-phenyl derivative by boiling with hydrobromic acid; (12) 1-dimethylamino - 3 - phenyl - 3 - pyrimidyl - (21) - hexanone - (4) from a - phenyl - a - pyrimidyl - (2) - butyric acid ethyl ester. Most of the products are converted to their succinate or maleate. In example (4) the product is separated into its isomers by fractional crystallization of the maleates. In each example the preparation of the specified starting material by a method analogous to that employed in the corresponding stage in example (1) is described.

  该发明包括公式<;FORM:0719237/IV（b）/1>;p中的基本酮，其中R1和R2分别代表具有高达6个碳原子的烷基基团或共同代表四元或五元二价残基，R3代表甲基基团或含有高达6个碳原子的烷基基团的亚甲基基团取代物，R4代表吡啶，噻唑或嘧啶的残基，其环碳原子直接与中央C原子相连，R5代表苯基，羟基苯基或烷氧基苯基基团，R7代表含有高达6个碳原子的烷基基团，以及这些基本酮的盐。通过将公式<;FORM:0719237/IV（b）/2>;的羧酸酯与烷基镁卤化物反应，如果需要，将所得的自由碱转化为盐，可以获得这样的化合物。当酯中的“烷基”是支链烷基时，通常可以获得更好的产率。上述化合物的盐是硫酸，盐酸，磷酸，乙酸，丙酸，苯甲酸和乙烯磺酸盐以及（用于鉴定目的）琥珀酸和马来酸盐。例如：（1）-苯基-α-吡啶基-(2)-γ-N-吡咯烷基-丁酸乙酯（通过在苏打胺存在下反应苯基-吡啶基-(2)-乙酸乙酯和N-b-氯乙基-吡咯烷基）与溴乙基镁反应，得到1-N-吡咯烷基-3-苯基-3-吡啶基-(2)-己酮，转化为其琥珀酸盐。类似地制备了（2）1-二甲基氨基-3-苯基-3-吡啶基-(21)-己酮-(4)来自-苯基-α-吡啶基-(2)-γ-二甲基氨基-丁酸乙酯；（3）1-N-吗啡基-3-苯基-3-吡啶基-(21)-己酮-(4)来自-苯基-α-吡啶基-(2)-γ-N-吗啡基-丁酸乙酯或异丙酯；（4）2-二甲基氨基-4-苯基-4-吡啶基-(21)-庚酮-(5)和1-二甲基氨基-2-甲基-3-苯基-3-吡啶基-(21)-己酮-(4)的异构混合物来自-苯基-α-吡啶基-(2)-γ-二甲基氨基-戊酸和-苯基-α-吡啶基-(2)-β-甲基-γ-二甲基氨基-丁酸乙酯的异构混合物；（5）1-二甲基氨基-3-苯基-3-吡啶基-(41)-己酮-(4)来自苯基-吡啶基-(4)-乙酸乙酯；（6）1-二甲基氨基-3-苯基-3-噻唑基-(21)-己酮-(4)来自-苯基-α-噻唑基-(2)-γ-二甲基氨基-丁酸乙酯；（7）1-N-吡咯烷基-3-苯基-3-噻唑基-(21)-己酮-(4)来自-苯基-α-噻唑基-(2)-γ-N-吡咯烷基-丁酸甲酯；（8）1-N-哌啶基-3-苯基-3-噻唑基-(21)-己酮-(4)来自-苯基-α-噻唑基-(2)-γ-N-哌啶基-丁酸甲酯；（9）1-N-吗啡基-3-苯基-3-噻唑基-(21)-己酮-(4)来自-苯基-α-噻唑基-(2)-γ-N-吗啡基-丁酸甲酯；（10）1-二乙基氨基-3-苯基-3-噻唑基-(21)-己酮-(4)来自-苯基-α-噻唑基-(2)-γ-二乙基氨基-丁酸乙酯；（11）1-二甲基氨基-3-(31-甲氧基-苯基)-3-噻唑基-(21)-己酮-(4)来自-（31-甲氧基-苯基）-α-噻唑基-(21)-γ-二甲基氨基-丁酸甲酯。通过与氢溴酸沸腾，将产物转化为相应的31-羟基苯基衍生物；（12）1-二甲基氨基-3-苯基-3-嘧啶基-(21)-己酮-(4)来自-苯基-α-嘧啶基-(2)-丁酸乙酯。大多数产品都转化为其琥珀酸盐或马来酸盐。在例（4）中，通过马来酸盐的分级结晶将产物分离成其异构体。在每个例子中，描述了通过类似于在例（1）中使用的方法制备指定起始材料的方法。