1-(4-methyl-2-morpholinomercapto-thiazol-5-yl)-ethanone | 99170-03-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-methyl-2-morpholinomercapto-thiazol-5-yl)-ethanone
• 英文别名: 1-(4-Methyl-2-morpholinomercapto-thiazol-5-yl)-aethanon；1-(4-Methyl-2-morpholin-4-ylsulfanyl-1,3-thiazol-5-yl)ethanone
• CAS: 99170-03-3
• 化学式: C₁₀H₁₄N₂O₂S₂
• 分子量: 258.365
• InChiKey: MGXHDDMPIZFOMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  96
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-氯-2,4-戊二酮 在 sodium hydroxide 、 sodium hypochlorite 、 硫酸 作用下， 生成 1-(4-methyl-2-morpholinomercapto-thiazol-5-yl)-ethanone
  参考文献：
  名称：

  5-acyl-2-mercaptothiazoles

  摘要：

  公开号：

  US02704761A1

文献信息

• 5-acyl-2-thiazolesulfenamides
  申请人：MONSANTO CHEMICALS

  公开号：US02841583A1

  公开（公告）日：1958-07-01

  The invention comprises compounds of the formula: <;FORM:0790800/IV (b)/1>; wherein R and R1 are hydrocarbon, chlorine-substituted hydrocarbon, alkoxy, carbonyl, carbalkoxy-substituted hydrocarbon radicals or sulphur-containing heterocyclic radicals having between them 8 to 20 carbon atoms, X-is the anion of a therapeutically acceptable non-toxic acid and Z contains not more than 7 carbon atoms and is a carbalkoxy radical, carbamyl radical, N-dialkylcarbamyl radical, benzoyl radical, acetyl radical or hydrogen. Such compounds are obtained by quaternizing a compound of the general formula: <;FORM:0790800/IV (b)/2>; with a quaternizing agent of the general formula R1X where Z1 is a nitroso radical or an organic radical containing not more than seven carbon atoms and is a carbalkoxy, benzoyl, N-dialkylcarbamyl, carbamyl or acetyl radical, compounds wherein Z is hydrogen being prepared by the additional step of hydrolysing compounds wherein Z is a carbalkoxy radical or of hydrogenating compounds prepared from those wherein Z1 is a nitroso radical. In examples: (1) N-carbethoxy-N1-nonylpiperazine is reacted with methyl iodide to give N-carbethoxy - N1 - methyl - N1 - n - nonylpiperazinium iodide; (2) N - carbethoxy - N1 - methylpiperazine and n-dodecyl bromide are reacted to give N-carbethoxy-N1-methyl-N1-n-dodecylpiperazinium bromide; (3) N-nitroso-N1-benzylN1-methyl-piperazinium chloride is hydrogenated using a Raney nickel catalyst to give N-benzyl-N-methylpiperazinium chloride hydrochloride. In a generally similar manner to (1) there are prepared (4) N-carbethoxy-N1-allyl-N1(a - carbethoxyethyl) piperazinium bromide; (5) N - methyl - N - n - tridecylpiperazinium chloride hydrochloride; (6) N - benzoyl - N1-methyl - N1 - n - dodecylpiperazinium bromide; (7) N - dimethylcarbamyl - N1 - methyl - N1-benzylpiperazinium chloride; (8) N - carbethoxy - N1 - methyl - N1 - (2 - heptynyl) - piperazinium bromide. A list is given of similarly prepared compounds, the radicals in specific compounds being selected from (at Z) carbethoxy, carbomethoxy, benzoyl, acetyl, carbamyl, dimethylcarbamyl and hydrogen; (at R) methyl, ethyl, butyl, benzyl, phenethyl and allyl; and (at R1) heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, undecenyl, propynyl, heptynyl, benzyl, p-chlorobenzyl, 2,4-dichlorobenzyl, p-methoxybenzyl, o- and m-methylbenzyl, phenylallyl, benzoylmethyl, a - or b -thenyl, carbdodecyloxymethyl and a -carbethoxyethyl radicals. N - benzoyl - N1 - methylpiperazine and N - dimethyl - carbamyl - N1 - methylpiperazine are prepared by reaction of N-methylpiperazine with the appropriate acid chlorides.

  该发明涉及公式如下的化合物：<;FORM:0790800/IV (b)/1>; 其中R和R1是烃基，氯代烃基，烷氧基，羰基，羰基烷氧基取代的烃基基团或含硫杂环基团，它们之间有8到20个碳原子，X是治疗上可接受的无毒酸的阴离子，Z含有不超过7个碳原子，是羰基烷氧基基团，氨基甲酰基基团，N-二烷基氨基甲酰基基团，苯甲酰基基团，乙酰基基团或氢。这些化合物是通过用一般式为<;FORM:0790800/IV (b)/2>;的化合物与一般式为R1X的季铵化试剂季铵化得到的，其中Z1是亚硝基基团或含不超过七个碳原子的有机基团，是羰基烷氧基基团，苯甲酰基，N-二烷基氨基甲酰基，氨基甲酰基或乙酰基基团，其中Z为氢的化合物是通过额外的水解步骤制备的，其中Z为羰基烷氧基基团或氢化由Z1为亚硝基基团制备的化合物。例如：（1）N-羧乙氧基-N1-壬基哌嗪与碘甲烷反应，得到N-羧乙氧基-N1-甲基-N1-壬基哌嗪碘化铵；（2）N-羧乙氧基-N1-甲基哌嗪和正十二溴化物反应，得到N-羧乙氧基-N1-甲基-N1-正十二基哌嗪溴化铵；（3）N-亚硝基-N1-苄基N1-甲基哌嗪盐酸盐经Raney镍催化氢化，得到N-苄基-N-甲基哌嗪盐酸盐。类似于（1）的方式制备了（4）N-羧乙氧基-N1-烯丙基-N1（a-羧乙氧基乙基）哌嗪溴化铵；（5）N-甲基-N-正十三基哌嗪盐酸盐；（6）N-苯甲酰基-N1-甲基-N1-正十二基哌嗪溴化铵；（7）N-二甲基氨基甲酰基-N1-甲基-N1-苄基哌嗪盐酸盐；（8）N-羧乙氧基-N1-甲基-N1-（2-庚炔基）-哌嗪溴化铵。列出了类似制备的化合物的列表，特定化合物中的基团从（在Z处）羧乙氧基，羰甲氧基，苯甲酰基，乙酰基，氨基甲酰基，二甲基氨基甲酰基和氢中选择；（在R处）甲基，乙基，丁基，苄基，苯乙基和烯丙基中选择；（在R1处）庚基，辛基，壬基，癸基，十一烷基，十二烷基，十三烷基，十四烷基，十五烷基，十六烷基，十一烯基，丙炔基，庚炔基，苯甲基，对氯苯甲基，2,4-二氯苯甲基，对甲氧基苯甲基，邻-和间-甲基苯甲基，苯基烯丙基，苯甲酰甲基，α-或β-烯基，羧十二氧甲基和α-羧乙氧基乙基基团中选择。通过N-苯甲酰基-N1-甲基哌嗪和N-二甲基氨基甲酰基-N1-甲基哌嗪与适当的酸氯化物反应制备N-苯甲酰基-N1-甲基哌嗪和N-二甲基氨基甲酰基-N1-甲基哌嗪。

• Thiazolethiols and their Derivatives
  作者：John J. D'Amico

  DOI：10.1021/ja01097a029

  日期：1953.1