2-((chloromethyl)thio)-1-methyl-1H-imidazole | 83767-77-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-((chloromethyl)thio)-1-methyl-1H-imidazole
• 英文别名: 2-Chloromethylsulphenyl-1-methylimidazole；2-Chloromethylsulfenyl-1-methylimidazole；2-(chloromethylsulfanyl)-1-methylimidazole
• CAS: 83767-77-5
• 化学式: C₅H₇ClN₂S
• 分子量: 162.643
• InChiKey: BEBFLLGDRQNARP-UHFFFAOYSA-N

物化性质

• 沸点：
  265.3±42.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-((chloromethyl)thio)-1-methyl-1H-imidazole 生成
  参考文献：
  名称：

  Unexpected New Chemistry of the Bis(thioimidazolyl)methanes

  摘要：

  [GRAPHICS]The synthesis of the linkage isomers of the bis(thioimidazolyl)methane family of compounds, namely CH2(N-tim)(2) (1) and CH2(S-tiM)(2) (2) (where tim = thio(methyl)imidazolyl) has been reinvestigated in order to optimize the yields, to complete the characterization of these known compounds, and also to ascertain the effect of varying heteroatom binding on their electrochemistry. During the course of these studies, the reactive intermediate CICH2(S-tiM) (3) was isolated and characterized. The chloromethyl derivative 3 readily decomposes on warming to give the ionic compound [CH2-(mu-C4H5N2S)(2)CH2](Cl)(2) (4), which was converted to the hexafluorophosphate salt (5) and then was characterized by single-crystal X-ray diffraction. It was also shown that CH2(S-tiM)(2) (2) could be converted at temperatures greater than 120 degrees C to CH2(N-tim)(2) (1) by a thermal isomerization that proceeds via the remaining possible linkage isomer CH2(S-tim)(N-tim). Electrochemical studies on 1-3 in acetonitrile reveals that each undergoes irreversible (one electron per ring) oxidations above 0.7 V versus Ag/AgCl, while the ionic compound 5 shows an irreversible reduction wave centered at -1.09 V.

  DOI：

  10.1021/jo051101o
• 作为产物：
  描述：

  溴氯甲烷 、 甲巯咪唑 在 三乙胺 作用下， 以5.85 g (90%)的产率得到2-((chloromethyl)thio)-1-methyl-1H-imidazole
  参考文献：
  名称：

  Substituted pyrimidin-2-ones and the salts thereof

  摘要：

  通式为：##STR1## 的化合物（其中X代表卤素原子或三氟甲基基团；R.sup.1和R.sup.2分别代表氢原子或较低的烷基基团；Z为--O--，--S--，--SO--，--SO.sub.2 --或基团--NR.sup.4 --其中R.sup.4如下所定义或代表基团COR.sup.5，其中R.sup.5代表氢原子或可选择取代的芳香族、杂环、芳基烷基、较低的烷基或较低的烷氧基团；R代表C.sub.6-10碳环芳族或含有5-9个成员的不饱和或芳香杂环环，该环含有O、N和S中选定的一个或多个杂原子，并且可选择携带一个融合环的碳环或杂环基团，该碳环或杂环基团可以携带一个或多个C.sub.1-4烷基或苯基基团，这些基团可选择取代；或者，Z代表基团>NR.sup.4时，基团--ZR可以代表一个可选择携带一个融合环和/或可选择取代的杂环环，如R所定义；R.sup.3代表氢原子或较低的烷基、较低的烯基、较低的炔基、较低的烷酰基、较低的烯酰基、C.sub.7-16芳基烷基或C.sub.6-10芳基基团或一个5-9成员的不饱和或芳香杂环环）；并且，如有酸性或碱性基团存在，其盐；在对抗异常细胞增殖方面是有用的。该发明的化合物是通过烷基化、环闭合和氧化等方法制备的。

  公开号：

  US04596870A1

文献信息

• US4596870A
  申请人：——

  公开号：US4596870A

  公开（公告）日：1986-06-24
• US4705791A
  申请人：——

  公开号：US4705791A

  公开（公告）日：1987-11-10
• Substituted pyrimidin-2-ones and the salts thereof
  申请人：Nyegaard & Co. A.S.

  公开号：US04596870A1

  公开（公告）日：1986-06-24

  Compounds of the general formula: ##STR1## (wherein X represents a halogen atom or a trifluoromethyl group; R.sup.1 and R.sup.2 independently represent a hydrogen atom or a lower alkyl group; Z is --O--, --S--, --SO--, --SO.sub.2 -- or the group --NR.sup.4 -- wherein R.sup.4 is as defined for R hereinafter or represents the group COR.sup.5 in which R.sup.5 represents a hydrogen atom or an optionally substituted aryl, heterocyclic, aralkyl, lower alkyl or lower alkoxy group; R represents a C.sub.6-10 carbocyclic aromatic group or a heterocyclic group containing a 5-9 membered unsaturated or aromatic heterocyclic ring which ring contains one or more heteroatoms selected from O, N and S and optionally carries a fused ring which carbocyclic or heterocyclic group may carry one or more C.sub.1-4 alkyl or phenyl groups, said groups being optionally substituted; or, where Z represents the group >NR.sup.4, the group --ZR may represent a heterocyclic ring optionally carrying a fused ring and/or optionally substituted as defined for R; and R.sup.3 represents a hydrogen atom or a lower alkyl, lower alkenyl, lower alkynyl, lower alkanoyl, lower alkenoyl, C.sub.7-16 aralkyl or C.sub.6-10 arly group or a 5-9 membered unsaturated or aromatic heterocyclic ring); and, where acid or basic groups are present, the salts thereof; are useful in combating abnormal cell proliferation. The compounds of the invention are prepared by inter alia alkylation, ring closure and oxidation.

  通式为：##STR1## 的化合物（其中X代表卤素原子或三氟甲基基团；R.sup.1和R.sup.2分别代表氢原子或较低的烷基基团；Z为--O--，--S--，--SO--，--SO.sub.2 --或基团--NR.sup.4 --其中R.sup.4如下所定义或代表基团COR.sup.5，其中R.sup.5代表氢原子或可选择取代的芳香族、杂环、芳基烷基、较低的烷基或较低的烷氧基团；R代表C.sub.6-10碳环芳族或含有5-9个成员的不饱和或芳香杂环环，该环含有O、N和S中选定的一个或多个杂原子，并且可选择携带一个融合环的碳环或杂环基团，该碳环或杂环基团可以携带一个或多个C.sub.1-4烷基或苯基基团，这些基团可选择取代；或者，Z代表基团>NR.sup.4时，基团--ZR可以代表一个可选择携带一个融合环和/或可选择取代的杂环环，如R所定义；R.sup.3代表氢原子或较低的烷基、较低的烯基、较低的炔基、较低的烷酰基、较低的烯酰基、C.sub.7-16芳基烷基或C.sub.6-10芳基基团或一个5-9成员的不饱和或芳香杂环环）；并且，如有酸性或碱性基团存在，其盐；在对抗异常细胞增殖方面是有用的。该发明的化合物是通过烷基化、环闭合和氧化等方法制备的。
• Unexpected New Chemistry of the Bis(thioimidazolyl)methanes
  作者：Rosalice M. Silva、Mark D. Smith、James R. Gardinier

  DOI：10.1021/jo051101o

  日期：2005.10.1

  [GRAPHICS]The synthesis of the linkage isomers of the bis(thioimidazolyl)methane family of compounds, namely CH2(N-tim)(2) (1) and CH2(S-tiM)(2) (2) (where tim = thio(methyl)imidazolyl) has been reinvestigated in order to optimize the yields, to complete the characterization of these known compounds, and also to ascertain the effect of varying heteroatom binding on their electrochemistry. During the course of these studies, the reactive intermediate CICH2(S-tiM) (3) was isolated and characterized. The chloromethyl derivative 3 readily decomposes on warming to give the ionic compound [CH2-(mu-C4H5N2S)(2)CH2](Cl)(2) (4), which was converted to the hexafluorophosphate salt (5) and then was characterized by single-crystal X-ray diffraction. It was also shown that CH2(S-tiM)(2) (2) could be converted at temperatures greater than 120 degrees C to CH2(N-tim)(2) (1) by a thermal isomerization that proceeds via the remaining possible linkage isomer CH2(S-tim)(N-tim). Electrochemical studies on 1-3 in acetonitrile reveals that each undergoes irreversible (one electron per ring) oxidations above 0.7 V versus Ag/AgCl, while the ionic compound 5 shows an irreversible reduction wave centered at -1.09 V.