1-benzoyloxymethyl-3-carboethoxypyridinium chloride

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-benzoyloxymethyl-3-carboethoxypyridinium chloride
• 英文别名: ethyl 1-(benzoyloxymethyl)pyridin-1-ium-3-carboxylate;chloride
• 化学式: C₁₆H₁₆NO₄*Cl
• 分子量: 321.76
• InChiKey: MEQJEMRZORVUMG-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.03
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  烟酸乙酯 、 苯甲酸氯甲基 在 氮气 、 乙醚 、 ethanol-ether 作用下， 反应 10.0h， 以gave 2.18 g (0.007 mol), 35%, 1-benzoyloxymethyl-3-carboethoxypyridinium chloride, mp 138°-141°的产率得到1-benzoyloxymethyl-3-carboethoxypyridinium chloride
  参考文献：
  名称：

  Labile, non-heterocyclic quaternary ammonium salt/esters as transient

  摘要：

  提供以下式子（I）和（II）的不稳定的季铵盐：##STR1## 其中##STR2##代表三级脂肪胺；其中##STR3##代表不饱和胺；其中R代表从以下组中选择的成员：氢原子，C.sub.1-C.sub.8开链或环烷基，C.sub.1-C.sub.8烷氧基烷基，C.sub.1-C.sub.8酰氧基烷基，C.sub.1-C.sub.8卤代烷基，C.sub.1-C.sub.8羧基烷基，C.sub.2-C.sub.8烯基苯基，芳基和取代芳基，其取代基从以下组中选择：卤原子，O-较低烷基（C.sub.1-C.sub.4）基，O-酰基，硝基，羧基和羧乙氧基；其中R.sub.1可能相同或不同，表示由上述R定义的任何成员，但R.sub.1不能是氢原子；其中X为--O--或--S--；其中Y表示从卤原子或任何其他有机或无机一价等效阴离子的组中选择的成员；进一步规定，当R代表氢原子且R.sub.1代表甲基基团或苯基时，##STR4##分别不能表示三甲胺和吡啶或喹啉。上述化合物的特点是极易溶于水，并且在化学和/或酶解水解之前具有抗氧化，脱烷基化和质子化的抗性。在化学和/或酶解水解时，这些化合物将“裂解”，从而根据以下一般方案释放其活性成分或成分：##STR5## 换句话说，标题化合物水解（化学或酶解）按照上述反应方案释放三级胺或不饱和胺衍生物，醛，羧酸和氢卤酸（HX）。

  公开号：

  US04160099A1

文献信息

• Labile, non-heterocyclic quaternary ammonium salt/esters as transient
  申请人：Interx Research Corporation

  公开号：US04160099A1

  公开（公告）日：1979-07-03

  Labile quaternary ammonium salts of the following formula (I) and (II) are provided: ##STR1## wherein ##STR2## represents a tertiary aliphatic amine; wherein ##STR3## represents an unsaturated amine; wherein R represents a member selected from the group consisting of a hydrogen atom, a C.sub.1 -C.sub.8 open chain or cyclo alkyl group, a C.sub.1 -C.sub.8 alkoxyalkyl group, a C.sub.1 -C.sub.8 acyloxyalkyl group, a C.sub.1 -C.sub.8 haloalkyl group, a C.sub.1 -C.sub.8 carboxyalkyl group, a C.sub.2 -C.sub.8 alkenylphenyl group, an aryl group, and a substituted aryl group, whose substituents are selected from the group consisting of a halogen atom, an O-lower alkyl (C.sub.1 -C.sub.4) group, an O-acyl group, a nitro group, a carboxyl group, and a carboethoxy group; wherein R.sub.1 which may be the same or different, represents any member defined by R above with the proviso that R.sub.1 cannot be a hydrogen atom; wherein X is --O-- or --S--; and wherein Y represents a member selected from the group consisting of a halogen atom or any other organic or inorganic monovalent equivalent anion; With the further proviso that ##STR4## respectively cannot represent trimethylamine and pyridine or quinoline when R represents a hydrogen atom and R.sub.1 represents a methyl group or a phenyl group. The compounds described above are characterized by their extreme solubility and resistance to oxidation, dealkylation, and protonation prior to chemical and/or enzymatic hydrolysis. Upon chemical and/or enzymatic hydrolysis, these compounds will "cleave," thus releasing their active constituent or constituents, according to the following general scheme(s): ##STR5## In other words, the title compounds hydrolyze (chemically or enzymatically) releasing a tertiary amine or unsaturated amine derivative, an aldehyde, a carboxylic acid and a hydrogen halide (HX) per the above reaction scheme.

  提供以下公式（I）和（II）的不稳定的季铵盐： 其中，##STR2##表示三级脂肪胺；其中，##STR3##表示不饱和胺；其中，R表示从群组中选择的成员，该群组包括氢原子，C.sub.1-C.sub.8开链或环烷基，C.sub.1-C.sub.8烷氧基烷基，C.sub.1-C.sub.8酰氧基烷基，C.sub.1-C.sub.8卤代烷基，C.sub.1-C.sub.8羧基烷基，C.sub.2-C.sub.8烯基苯基，芳基和取代芳基，其取代基选择自卤原子，O-较低烷基（C.sub.1-C.sub.4）基，O-酰基，硝基，羧基和羧乙氧基；其中R.sub.1可以相同或不同，表示由上述R定义的任何成员，但R.sub.1不能是氢原子；其中X为--O--或--S--；Y表示从卤原子或任何其他有机或无机单价等效阴离子中选择的成员；并且还规定当R表示氢原子且R.sub.1表示甲基基团或苯基团时，##STR4##分别不能表示三甲胺和吡啶或喹啉。上述化合物的特点是极易溶解和耐氧化，去烷基化和质子化，在化学和/或酶解水解之前。在化学和/或酶解水解时，这些化合物将“断裂”，从而根据以下通用方案释放其活性成分：##STR5##换句话说，标题化合物水解（化学或酶解）会根据上述反应方案释放三级胺或不饱和胺衍生物，醛，羧酸和氢卤酸（HX）。
• US4160099A
  申请人：——

  公开号：US4160099A

  公开（公告）日：1979-07-03
• US4727151A
  申请人：——

  公开号：US4727151A

  公开（公告）日：1988-02-23
• Labile quaternary ammonium salts as prodrugs
  申请人：INTERx Research Corporation

  公开号：US04727151A1

  公开（公告）日：1988-02-23

  Labile quaternary ammonium salts of the following formula (I) and (II) are provided: ##STR1## wherein N represents a tertiary aliphatic amine; wherein N represents an unsaturated amine; wherein R represents a member selected from the group consisting of a hydrogen atom, a C.sub.1 -C.sub.8 open chain or cyclo alkyl group, a C.sub.1 -C.sub.8 alkoxyalkyl group, a C.sub.1 -C.sub.8 acyloxyalkyl group, a C.sub.1 -C.sub.8 haloalkyl group, a C.sub.1 -C.sub.8 carboxyalkyl group, a C.sub.2 -C.sub.8 alkenylphenyl group, an aryl group, and a substituted aryl group, whose substituents are selected from the group consisting of a halogen atom, an O-lower alkyl (C.sub.1 -C.sub.4) group, an O-acyl group, a nitro group, a carboxyl group, and a carboethoxy group; wherein R.sub.1 which may be the same or different, represents any member defined by R above with the proviso that R.sub.1 cannot be a hydrogen atom; wherein X is --O-- or --S--; and wherein Y represents a member selected from the group consisting of a halogen atom or any other organic or inorganic monovalent equivalent anion; with the further proviso that N and N, respectively cannot represent trimethylamine and pyridine or quinoline when R represents a hydrogen atom and R.sub.1 represents a methyl group or a phenyl group. The compounds described above are characterized by their extreme solubility and resistance to oxidation, dealkylation, and protonation prior to chemical and/or enzymatic hydrolysis. Upon chemical and/or enzymatic hydrolysis, these compounds will "cleave," thus releasing their active constituent or constituents, according to the following general scheme(s): ##STR2## In other words, the title compounds hydrolyze (chemically or enzymatically) releasing a tertiary amine or unsaturated amine derivative, an aldehyde, a carboxylic acid and a hydrogen halide (HX) per the above reaction scheme.

  提供以下公式（I）和（II）的不稳定的季铵盐： ##STR1## 其中N代表三级脂肪胺；其中N代表不饱和胺；其中R代表从羟基，C.sub.1-C.sub.8开链或环烷基，C.sub.1-C.sub.8烷氧基烷基，C.sub.1-C.sub.8酰氧基烷基，C.sub.1-C.sub.8卤代烷基，C.sub.1-C.sub.8羧基烷基，C.sub.2-C.sub.8烯基苯基，芳基和取代芳基中选择的成员，其取代基选择自卤素原子，O-低烷基（C.sub.1-C.sub.4）基团，O-酰基基团，硝基，羧基和羧乙氧基；其中R.sub.1可以相同或不同，表示由上述R定义的任何成员，但有条件R.sub.1不能是氢原子；其中X为--O--或--S--；其中Y表示从卤素原子或任何其他有机或无机单价等效阴离子中选择的成员；另外有条件，当R表示氢原子且R.sub.1表示甲基基团或苯基时，N和N不能分别表示三甲胺和吡啶或喹啉。上述化合物的特点是极易溶解和抗氧化，去烷基化和质子化，在化学和/或酶解水解之前。在化学和/或酶解水解时，这些化合物将“裂解”，从而根据以下一般方案释放其活性成分或成分： ##STR2## 换句话说，标题化合物水解（化学或酶解）释放三级胺或不饱和胺衍生物，醛，羧酸和氢卤酸（HX）按上述反应方案。