cycloheptyloxymethyl chloride | 117941-76-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cycloheptyloxymethyl chloride
• 英文别名: Chloromethoxycycloheptane
• CAS: 117941-76-1
• 化学式: C₈H₁₅ClO
• 分子量: 162.66
• InChiKey: WZWNESWEDCUIJX-UHFFFAOYSA-N

物化性质

• 沸点：
  212.8±13.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N-二甲基正辛胺 、 cycloheptyloxymethyl chloride 以 正庚烷 为溶剂， 反应 0.17h， 以94%的产率得到Cycloheptyloxymethyl-dimethyl-octylazanium;chloride
  参考文献：
  名称：

  Synthesis and antimicrobial activities of new quats

  摘要：

  制备了高产率的（烷氧甲基）十二烷基二甲基铵、（环烷氧甲基）十二烷基二甲基铵、（烷基硫甲基）十二烷基二甲基铵、（烷氧甲基）二甲基辛基铵、（环烷氧甲基）二甲基辛基铵和（烷基硫甲基）二甲基辛基铵的氯化物。所研究的所有氯化物均表现出抗菌活性。利用粗糙集方法分析了化学结构与抗菌活性之间的关系。

  DOI：

  10.1016/s0223-5234(97)83292-8
• 作为产物：
  描述：

  三聚甲醛 、 环庚醇 在 盐酸 作用下， 以 苯 为溶剂， 反应 2.5h， 以75%的产率得到cycloheptyloxymethyl chloride
  参考文献：
  名称：

  Quaternary salts of 2-[(hydroxyimino)methyl]imidazole. 2. Preparation and in vitro and in vivo evaluaton of 1-(alkoxymethyl)-2-[(hydroxyimino)methyl]-3-methylimidazolium halides for reactivation of organophosphorus-inhibited acetylcholinesterases

  摘要：

  A series of structurally related mono- and bis-1,3-disubstituted 2-[(hydroxyimino)methyl]imidazolium halides were evaluated in vitro for their ability to reactivate electric eel, bovine, and human erythrocyte (RBC) acetylcholinesterases (AChE) inhibited by ethyl p-nitrophenyl methylphosphonate (EPMP) and 3,3-dimethyl-2-butyl methyl-phosphonofluoridate (soman, GD). All new compounds were characterized for (hydroxyimino)methyl acid dissociation constant, nucleophilicity, octanol-buffer partition coefficient, reversible AChE inhibition, and kinetics of reactivation of EPMP-inhibited AChEs. For GD-inhibited AChEs, maximal reactivation was used to compare compounds since rapid phosphonyl enzyme dealkylation "aging" complicated interpretation of kinetic constants. For comparison, we also evaluated three known pyridinium therapeutics, 2-PAM, HI-6, and toxogonin. In vivo evaluation in mice revealed that when selected imidazolium compounds were coadministered with atropine sulfate, they were effective in providing lifesaving protection against both GD and EPMP challenges. This was a major accomplishment in the search for effective anticholinesterase therapeutics--the synthesis and preliminary evaluation of the first new monoquaternary soman antidotes with potencies superior to 2-PAM. Significantly, there was an apparent inverse relationship between in vitro and in vivo results; the most potent in vivo compounds proved to be the poorest in vitro reactivators. These results suggested that an alternative and possibly novel antidotal mechanism of protective action may be applicable for the imidazolium aldoximes. Selected compounds were also evaluated for their inhibition of AChE phosphorylation by GD and antimuscarinic and antinicotinic receptor blocking effects.

  DOI：

  10.1021/jm00122a034

文献信息

• Synthesis and Antibiotic Activity of 1-Cycloalkoxymethyl-4-dimethylaminopyridinium and 1-[(1-Alkoxy)ethyl]-4-dimethylaminopyridinium Chlorides
  作者：Juliusz Pernak、Lucyna Michalak、Jerzy Krysinski、Zbigniew Kuncewicz

  DOI：10.1002/ardp.19953280611

  日期：——

  (2a–2h) pyridinium chlorides. Reaction of these chlorides with NaOH produces the corresponding 4‐pyridones. All the chlorides synthesized showed antibiotic activity. Particularly high activity against microbes representing cocci, rods, fungi, and bacilli was shown by 1‐cyclododecyloxymethyl‐4‐dimethylaminopyridinium chloride 1d and 1‐[(1‐dodecyloxy)ethyl]‐4‐dimethylaminopyridinium chloride 2f.

  DMAP 很容易与氯甲基环烷基醚和 α-氯乙基烷基醚反应，生成稳定的 (1a – 1e) 和不稳定的 (2a – 2h) 氯化吡啶鎓。这些氯化物与 NaOH 反应生成相应的 4-吡啶酮。所有合成的氯化物都显示出抗生素活性。1- 环十二烷氧基甲基 - 4- 二甲基氨基吡啶鎓氯化物 1d 和 1 - [（1 - 十二烷氧基）乙基] -4 - 二甲基氨基吡啶鎓氯化物 2f 显示出对代表球菌、杆状体、真菌和杆菌的微生物具有特别高的活性。
• Synthesis and Antimicrobial Activity of New Quaternary Ammonium Chlorides
  作者：Bogumil Brycki、Andrzej Skrzypczak、Ilona Mirska、Juliusz Pernak

  DOI：10.1002/ardp.19963290603

  日期：——

  ethers or sulfides, chloromethylbezyl ethers or sulfides and chloromethylcycloalkyl ethers to give quaternary ammonium chlorides in very good yields. All the chlorides studied showed antimicrobial activity. The relationship between the chemical structure and antimicrobial activity was analyzed by rough sets.

  癸基二甲胺很容易与氯甲基烷基醚或硫化物、氯甲基苄基醚或硫化物和氯甲基环烷基醚反应，以非常好的收率得到季铵氯化物。所研究的所有氯化物均显示出抗微生物活性。通过粗糙集分析化学结构与抗菌活性之间的关系。
• Synthesis and Antimicrobial Activity of New 1-Benzylbenzimidazolium Chlorides
  作者：Juliusz Pernak、Anita Arndt、Bogumil Brycki

  DOI：10.1002/ardp.19973300805

  日期：——

  3‐alkylthiomethyl‐1‐benzylbenzimidazolium or 1‐benzyl‐3‐cycloalkoxymethylbenzimidazolium chlorides in very good yields. All the 1‐benzylbenzimidazolium chlorides showed antimicrobial activity. The relationship between chemical structure and antimicrobial activity was analyzed by quantitative structure‐activity relationships (QSAR).

  1-苄基苯并咪唑与氯甲基烷基醚或硫化物或氯甲基环烷基醚反应，以非常好的收率生成 3-烷氧基-甲基-1-苄基苯并咪唑鎓或 3-烷硫基甲基-1-苄基苯并咪唑鎓或 1-苄基-3-环烷氧基甲基苯并咪唑鎓氯化物。所有 1-苄基苯并咪唑氯化物均表现出抗菌活性。通过定量构效关系(QSAR)分析化学结构与抗菌活性之间的关系。
• Antimicrobial activities of new analogues of benzalkonium chloride
  作者：J Pernak

  DOI：10.1016/s0223-5234(99)00216-0

  日期：1999.9
• Quaternary salts of 2-[(hydroxyimino)methyl]imidazole. 2. Preparation and in vitro and in vivo evaluaton of 1-(alkoxymethyl)-2-[(hydroxyimino)methyl]-3-methylimidazolium halides for reactivation of organophosphorus-inhibited acetylcholinesterases
  作者：Clifford D. Bedford、Ralph N. Harris、Robert A. Howd、Dane A. Goff、Gary A. Koolpe、M. Petesch、Alexi Miller、Harold W. Nolen、H. A. Musallam

  DOI：10.1021/jm00122a034

  日期：1989.2

  A series of structurally related mono- and bis-1,3-disubstituted 2-[(hydroxyimino)methyl]imidazolium halides were evaluated in vitro for their ability to reactivate electric eel, bovine, and human erythrocyte (RBC) acetylcholinesterases (AChE) inhibited by ethyl p-nitrophenyl methylphosphonate (EPMP) and 3,3-dimethyl-2-butyl methyl-phosphonofluoridate (soman, GD). All new compounds were characterized for (hydroxyimino)methyl acid dissociation constant, nucleophilicity, octanol-buffer partition coefficient, reversible AChE inhibition, and kinetics of reactivation of EPMP-inhibited AChEs. For GD-inhibited AChEs, maximal reactivation was used to compare compounds since rapid phosphonyl enzyme dealkylation "aging" complicated interpretation of kinetic constants. For comparison, we also evaluated three known pyridinium therapeutics, 2-PAM, HI-6, and toxogonin. In vivo evaluation in mice revealed that when selected imidazolium compounds were coadministered with atropine sulfate, they were effective in providing lifesaving protection against both GD and EPMP challenges. This was a major accomplishment in the search for effective anticholinesterase therapeutics--the synthesis and preliminary evaluation of the first new monoquaternary soman antidotes with potencies superior to 2-PAM. Significantly, there was an apparent inverse relationship between in vitro and in vivo results; the most potent in vivo compounds proved to be the poorest in vitro reactivators. These results suggested that an alternative and possibly novel antidotal mechanism of protective action may be applicable for the imidazolium aldoximes. Selected compounds were also evaluated for their inhibition of AChE phosphorylation by GD and antimuscarinic and antinicotinic receptor blocking effects.