2-(piperidin-1-ylmethyl)-4-(2,4,4-trimethylpentan-2-yl)phenol | 5414-83-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 2-(piperidin-1-ylmethyl)-4-(2,4,4-trimethylpentan-2-yl)phenol
• 英文别名: ZINC1706378；NSC10650；2-Piperidinomethyl-4-(1,1,3,3-tetramethyl-butyl)-phenol
• CAS: 5414-83-5
• 化学式: C₂₀H₃₃NO
• 分子量: 303.488
• InChiKey: GWNLLAJONXXKEC-UHFFFAOYSA-N

物化性质

• 熔点：
  92-93 °C
• 沸点：
  173-176 °C(Press: 0.5 Torr)
• 密度：
  0.988±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(piperidin-1-ylmethyl)-4-(2,4,4-trimethylpentan-2-yl)phenol 、 碘甲烷 生成 1-[2-hydroxy-5-(1,1,3,3-tetramethyl-butyl)-benzyl]-1-methyl-piperidinium; iodide
  参考文献：
  名称：

  Phenolic Invert Soaps

  摘要：

  DOI：

  10.1021/ja01852a504
• 作为产物：
  描述：

  哌啶 、 聚合甲醛 、 对特辛基苯酚 在 乙醇 作用下， 生成 2-(piperidin-1-ylmethyl)-4-(2,4,4-trimethylpentan-2-yl)phenol
  参考文献：
  名称：

  Soap Forming Compounds and Process of making same

  摘要：

  基本产品是通过甲醛、含有少于七个碳原子的非芳香性二级胺与苯酚相互作用而获得的，该苯酚在核中被取代为含有三个以上碳原子的烃基，并且至少有一个自由的羟基位。苯酚可以是单环或多环的，除了烃基外，还可以含有其他核取代基，如额外的羟基、卤素原子、烷基、烷氧基、硝基、氨基或甲醛基；醛基或自由酸基，如磺酸基或羧酸基，不得存在。烃基可以是芳香性或烷烃烃基，或者是含有三个以上碳原子的直链或支链脂肪烃基。指定的苯酚包括丁基苯酚、溴丁基苯酚、氯丁基苯酚、碘丁基苯酚，相应的戊基、己基、庚基、辛基、十二基、十六基和十八基苯酚，环己基苯酚、萜基苯酚、四氢萘基苯酚、苯基苯酚和苄基苯酚，以及相应的甲酚、间苯二酚、对羟基苯酚或萘酚衍生物。粗制的取代苯酚可以使用，例如通过在硫酸存在下处理苯酚，与三个以上碳原子的烯烃反应，然后中和混合物而获得的。在这种方式中指定用于使用的烯烃包括丁烯、戊烯、己烯、辛烯、三异丁烯和四异丁烯，以及通过石油裂解获得的二烯和更高的烯烃。指定的二级胺包括二甲胺、二乙胺、甲乙胺、二异丙胺、二乙醇胺、二正丙胺、吡啶和哌嗪；含有一级氨基或自由酸基的二级胺的使用被排除。试剂可以同时进行反应，最好在惰性溶剂中进行，例如醇、醚、苯或二噁烷中，并在碱的存在或缺席下进行。或者，苯酚可以添加到胺和甲醛的反应产物中。每摩尔苯酚至少取一摩尔甲醛和胺。反应可以在大气温度或升温下进行。与水溶性酸盐如乙酸、磷酸、乳酸、葡萄糖酸、草酸、硫酸、盐酸或氢氟酸的盐对产品有用，用作染色、洗涤和漂白中的润湿、清洁和乳化剂，用作酸性介质中的杀菌剂，用作脂肪分解催化剂。通过用有机卤化物如苄氯、有机硫酸酯如二甲基硫酸酯或氯甲酸乙酯处理产品获得的季铵盐具有类似的性质。与水不溶酸如高级脂肪酸、萘酚酸或树脂酸的盐在油中和烃中溶解，并用作乳化剂、蜡替代品、增塑剂、橡胶组合物的成分和染料的中间体。在示例中，从以下反应中获得产品：（1）甲醛、二甲胺或二乙胺和对叔丁基苯酚、对叔戊基苯酚、对苯基苯酚或对环己基苯酚；（2）甲醛、二甲胺和邻苯基苯酚或对苯基苯酚；（3）甲醛、吡啶和α,α,γ,γ-四甲基丁基苯酚；（4）甲醛、二甲胺、二乙胺或二乙醇胺和α,α,γ,γ-四甲基丁基苯酚；（5）甲醛、二甲胺和（a）由苯酚与三异丁烯在硫酸存在下缩合得到的十二基苯酚混合物，（b）由苯酚与四异丁烯在硫酸存在下缩合得到的十六基苯酚混合物，或（c）由苯酚与月桂醇在氯化锌存在下缩合得到的月桂基苯酚，或（d）由苯酚与月桂醇在氯化锌存在下缩合得到的十六烷基苯酚；（6）甲醛、二甲胺和α,α,γ,γ-四甲基丁基-p-甲酚；（7）甲醛、二甲胺和（a）α,α,γ,γ-四甲基丁基间苯二酚，由邻苯二酚与二异丁烯在硫酸存在下缩合得到，或（b）正己基间苯二酚。此外，通过甲醛、含有少于七个碳原子的非芳香性二级胺与苯酚相互作用，且该苯酚在核中被取代为含有三个以上碳原子的烃基，并且至少有一个自由的羟基位，可以获得基本产品。苯酚可以是单环或多环的，除了烃基外，还可以含有其他核取代基，如额外的羟基、卤素原子、烷基、烷氧基、硝基、氨基或甲醛基；醛基或自由酸基，如羧酸基或磺酸基，不得存在。烃基可以是芳香性或烷烃烃基，或者是含有三个以上碳原子的直链或支链脂肪烃基。指定的苯酚包括丁基苯酚、溴丁基苯酚、氯丁基苯酚、碘丁基苯酚，相应的戊基、己基、庚基、辛基、十二基、十六基和十八基苯酚，环己基苯酚、萜基苯酚、四氢萘基苯酚、苯基苯酚和苄基苯酚，以及相应的甲酚、间苯二酚、对羟基苯酚或萘酚衍生物。指定的二级胺包括二甲胺、二乙胺、甲乙胺、二异丙胺、二乙醇胺、二正丙胺、吡啶和哌嗪；含有一级氨基或自由酸基的二级胺的使用被排除。与水不溶酸如高级脂肪酸、萘酚酸或树脂酸的盐在油中和烃中溶解，并用作增塑剂和橡胶组合物的成分。在示例中，从以下反应中获得产品：（1）甲醛、二甲胺或二乙胺和对叔丁基苯酚、对叔戊基苯酚、对苯基苯酚或对环己基苯酚；（2）甲醛、二甲胺和邻苯基苯酚或对苯基苯酚；（3）甲醛、吡啶和α,α,γ,γ-四甲基丁基苯酚；（4）甲醛、二甲胺、二乙胺或二乙醇胺和α,α,γ,γ-四甲基丁基苯酚；（5）甲醛、二甲胺和（a）十二基苯酚混合物，（b）十六基苯酚混合物或（c）月桂基苯酚，或（d）十六烷基苯酚；（6）甲醛、二甲胺和α,α,γ,γ-四甲基丁基-p-甲酚；（7）甲醛、二甲胺和（a）α,α,γ,γ-四甲基丁基间苯二酚或（b）正己基间苯二酚。

  公开号：

  US02033092A1

文献信息

• Soap Forming Compounds and Process of making same
  申请人：ROEHM & HAAS COMPANY

  公开号：US02033092A1

  公开（公告）日：1936-03-03

  Basic products are obtained by the interaction of formaldehyde, a non - aromatic secondary amine containing less than seven carbon atoms, and a phenol substituted in the nucleus with a hydrocarbon radicle of more than three carbon atoms and having at least one free o-position to the hydroxyl group. The phenol may be mono- or poly-cyclic, and may contain, in addition to the hydrocarbon radicle, other nuclear substituents such as additional hydroxyl groups, halogen atoms, or alkyl, alkoxy, nitro, amino or methylol groups; aldehyde groups or free acid groups, such as sulphonic or carboxylic groups, must not be present. The hydrocarbon radicle may be an aromatic or hydroaromatic radicle, or a straight or branched aliphatic radicle of more than three carbon atoms. Specified phenols are butylphenols, butylbromophenols, butylchlorophenols, butyliodophenols, the corresponding amyl-, hexyl-, heptyl-, octyl-, dodecyl-, hexadecyl-, and octadecyl-phenols, cyclohexyl-phenols, bornylphenols, tetrahydronaphthylphenols, phenylphenols, and benzylphenols, and the corresponding cresol, resorcinol, hydroquinone or naphthol derivatives. Crude substituted phenols may be used such as are obtainable by treating a phenol, in the presence of sulphuric acid, with an olefine of more than three carbon atoms, and neutralizing the mixture; olefines specified for use in this way are butylenes, amylenes, hexenes, octenes, triand tetra-isobutylene, diamylene and higher olefines obtained by cracking petroleum. Specified secondary amines are dimethylamine, diethylamine, methylethylamine, diisopropylamine, diethanolamine, di - n - propylamine, piperidine and piperazine; the use of secondary amines containing primary amino or free acid groups is excluded. The reagents may be brought to reaction simultaneously, preferably in an inert solvent such as alcohol, ether, benzene or dioxane, and in the presence or absence of a trace of an alkali, such as soda or caustic soda. Alternatively, the phenol may be added to the reaction product of the amine and formaldehyde. At least one mol. of formaldehyde and of amine is taken per mol. of phenol. The reaction may be effected at atmospheric or raised temperature. The salts of the products with water-soluble acids, e.g. acetic, phosphoric, lactic, gluconic, oxalic, sulphuric, hydrochloric or hydrofluoric acid, are useful (a) as wetting, cleansing and emulsifying agents in dyeing, laundering and bleaching, (b) as bactericides in acidic media, and (c) as fat-splitting catalysts. The quaternary ammonium salts obtained by treating the products with organic halides such as benzyl chloride, with organic sulphates such as dimethyl sulphate, or with ethyl chloroformate have similar properties. The salts of the products with water-insoluble acids, e.g. higher fatty, naphthenic or resin acids, are soluble in oils and hydrocarbons and are useful as emulsifying agents, wax substitutes, plasticizers, ingredients of rubber compositions, and intermediates for dyes. In the examples, products are obtained from (1) formaldehyde, dimethylamine or diethylamine, and p-tert.-butylphenol, p-tert.-amylphenol, p-benzylphenol, or p-cyclohexylphenol; (2) formaldehyde, dimethylamine, and o-phenylphenol or p-phenylphenol; (3) formaldehyde, piperidine, and a , a , g , g -tetramethylbutylphenol; (4) formaldehyde, dimethylamine, diethylamine, or diethanolamine, and a , a , g , g -tetramethylbutylphenol; (5) formaldehyde, dimethylamine, and (a) a dodecylphenol mixture obtained by condensing phenol with tri-isobutylene in the presence of sulphuric acid, or (b) a hexadecylphenol mixture obtained by condensing phenol with tetraisobutylene in the presence of sulphuric acid, or (c) laurylphenol, obtained by condensing phenol with lauryl alcohol in the presence of zinc chloride, or (d) cetylphenol, made by condensing phenol with cetyl alcohol in the presence of zinc chloride; (6) formaldehyde, dimethylamine, and a , a , g , g -tetramethylbutyl-p-cresol, obtained by condensing p-cresol with diisobutylene in the presence of sulphuric acid; (7) formaldehyde, dimethylamine, and (a) a , a , g , g -tetramethylbutylresorcinol, obtained by condensing resorcinol with diisobutylene in the presence of sulphuric acid, or (b) n-hexylresorcinol.ALSO:Basic products are obtained by the interaction of formaldehyde, a non-aromatic secondary amine containing less than seven carbon atoms, and a phenol substituted in the nucleus with a hydrocarbon radicle of more than three carbon atoms and having at least one free o-position to the hydroxyl group. The phenol may be mono- or polycyclic, and may contain, in addition to the hydrocarbon radicle, other nuclear substituents such as additional hydroxyl groups, halogen atoms, or alkyl, alkoxy, nitro, amino or methylol groups; aldehyde groups or free acid groups, such as sulphonic or carboxylic groups, must not be present. The hydrocarbon radicle may be an aromatic or hydroaromatic radicle, or a straight or branched aliphatic radicle of more than three carbon atoms. Specified phenols are butylphenols, butylbromo-phenols, butylchlorophenols, butyliodophenols, the corresponding amyl-, hexyl-, heptyl-, octyl-, dodecyl-, hexadecyl-, and octadecyl-phenols, cyclohexylphenols, bornylphenols, tetrahydronaphthylphenols, phenylphenols, and benzylphenols, and the corresponding cresol, resorcinol, hydroquinone or naphthol derivatives. Specified secondary amines are dimethylamine, diethylamine, methylethylamine, diisopropylamine, diethanolamine, di-n-propylamine, piperidine and piperazine; the use of secondary amines containing primary amino or free acid groups is excluded. The salts of the products with water-soluble acids, e.g., acetic, phosphoric, lactic, gluconic, oxalic, sulphuric, hydrochloric or hydrofluoric acid, are useful as emulsifying agents in dyeing, laundering and bleaching, and as fat-splitting catalysts. The quaternary ammonium salts obtained by treating the products with organic halides such as benzyl chloride, with organic sulphates such as dimethyl sulphate, or with ethyl chloroformate have similar properties. The salts of the products with water-insoluble acids, e.g., higher fatty, naphthenic or resin acids, are soluble in oils and hydrocarbons and are useful as emulsifying agents. In the examples, products are obtained from (1) formaldehyde, dimethylamine or diethylamine, and p-tert.-butylphenol, p-tert.-amylphenol, p-benzylphenol, or p-cyclohexylphenol; (2) formaldehyde, dimethylamine, and o-phenylphenol or p-phenylphenol; (3) formaldehyde, piperidine, and a g , a , g , g , -tetramethylbutylphenol; (4) formaldehyde, dimethylamine, diethylamine, or diethanolamine, and a , a , g , g , -tetramethylbutylphenol; (5) formaldehyde, dimethylamine, and (a) a dodecylphenol mixture, (b) a hexadecylphenol mixture or (c) laurylphenol, or (d) cetyphenol, (6) formaldehyde, dimethylamine, and a , a , g , g , -tetramethylbutyl-p-cresol; (7) formaldehyde, dimethylamine, and (a) a , a , g , g , -tetramethylbutylresorcinol or (b) n-hexylresorcinol.ALSO:Basic products are obtained by the interaction of formaldehyde, a nonaromatic secondary amine containing less than seven carbon atoms, and a phenol substituted in the nucleus with a hydrocarbon radicle of more than three carbon atoms and having at least one free o-position to the hydroxyl group. The phenol may be mono- or poly-cyclic, and may contain, in addition to the hydrocarbon radicle, other nuclear substituents such as additional hydroxyl groups, halogen atoms, or alkyl, alkoxy, nitro, amino or methylol groups; aldehyde groups or free acid groups, such as carboxylic or sulphonic groups, must not be present. The hydrocarbon radicle may be an aromatic or hydroaromatic radicle, or a straight or branched aliphatic radicle of more than three carbon atoms. Specified phenols are butylphenols, butylbromo-phenols, butylchlorophenols, butyliodophenols, the corresponding amyl-, hexyl-, heptyl-, octyl-, dodecyl-, hexadecyl-, and octadecyl-phenols, cyclohexylphenols, bornylphenols, tetrahydronaphthylphenols, phenylphenols, and benzylphenols, and the corresponding cresol, resorcinol, hydroquinone or naphthol derivatives. Specified secondary amines are dimethylamine, diethylamine, methylethylamine, diisopropylamine, diethanolamine, di-n-propylamine, piperidine and piperazine; the use of secondary amines containing primary amino or free acid groups is excluded. The salts of the products with water-insoluble acids, e.g. higher fatty, naphthenic or resin acids, are soluble in oils and hydrocarbons and are useful as plasticizers and ingredients of rubber compositions. In the examples, products are obtained from (1) formaldehyde, dimethylamine or diethylamine, and p-tert.-butylphenol, p-tert-amylphenol, p-benzylphenol, or p-cyclohexylphenol; (2) formaldehyde, dimethylamine, and o-phenylphenol or p-phenylphenol; (3) formaldehyde, piperidine, and a , a , g , g , -tetramethyl-butylphenol; (4) formaldehyde, dimethylamine, diethylamine, or diethanolamine, and a , a , g , g , -tetramethylbutylphenol; (5) formaldehyde, dimethylamine, and (a) a dodecylphenol mixture or (b) a hexadecylphenol mixture or (c) laurylphenol, or (d) cetyphenol; (6) formaldehyde, dimethylamine, and a , a , g , g , -tetramethylbutyl-p-cresol; (7) formaldehyde, dimethylamine, and (a) a , a , g , g -tetramethylbutylresorcinol or (b) n-hexylresorcinol.

  基本产品是通过甲醛、含有少于七个碳原子的非芳香性二级胺与苯酚相互作用而获得的，该苯酚在核中被取代为含有三个以上碳原子的烃基，并且至少有一个自由的羟基位。苯酚可以是单环或多环的，除了烃基外，还可以含有其他核取代基，如额外的羟基、卤素原子、烷基、烷氧基、硝基、氨基或甲醛基；醛基或自由酸基，如磺酸基或羧酸基，不得存在。烃基可以是芳香性或烷烃烃基，或者是含有三个以上碳原子的直链或支链脂肪烃基。指定的苯酚包括丁基苯酚、溴丁基苯酚、氯丁基苯酚、碘丁基苯酚，相应的戊基、己基、庚基、辛基、十二基、十六基和十八基苯酚，环己基苯酚、萜基苯酚、四氢萘基苯酚、苯基苯酚和苄基苯酚，以及相应的甲酚、间苯二酚、对羟基苯酚或萘酚衍生物。粗制的取代苯酚可以使用，例如通过在硫酸存在下处理苯酚，与三个以上碳原子的烯烃反应，然后中和混合物而获得的。在这种方式中指定用于使用的烯烃包括丁烯、戊烯、己烯、辛烯、三异丁烯和四异丁烯，以及通过石油裂解获得的二烯和更高的烯烃。指定的二级胺包括二甲胺、二乙胺、甲乙胺、二异丙胺、二乙醇胺、二正丙胺、吡啶和哌嗪；含有一级氨基或自由酸基的二级胺的使用被排除。试剂可以同时进行反应，最好在惰性溶剂中进行，例如醇、醚、苯或二噁烷中，并在碱的存在或缺席下进行。或者，苯酚可以添加到胺和甲醛的反应产物中。每摩尔苯酚至少取一摩尔甲醛和胺。反应可以在大气温度或升温下进行。与水溶性酸盐如乙酸、磷酸、乳酸、葡萄糖酸、草酸、硫酸、盐酸或氢氟酸的盐对产品有用，用作染色、洗涤和漂白中的润湿、清洁和乳化剂，用作酸性介质中的杀菌剂，用作脂肪分解催化剂。通过用有机卤化物如苄氯、有机硫酸酯如二甲基硫酸酯或氯甲酸乙酯处理产品获得的季铵盐具有类似的性质。与水不溶酸如高级脂肪酸、萘酚酸或树脂酸的盐在油中和烃中溶解，并用作乳化剂、蜡替代品、增塑剂、橡胶组合物的成分和染料的中间体。在示例中，从以下反应中获得产品：（1）甲醛、二甲胺或二乙胺和对叔丁基苯酚、对叔戊基苯酚、对苯基苯酚或对环己基苯酚；（2）甲醛、二甲胺和邻苯基苯酚或对苯基苯酚；（3）甲醛、吡啶和α,α,γ,γ-四甲基丁基苯酚；（4）甲醛、二甲胺、二乙胺或二乙醇胺和α,α,γ,γ-四甲基丁基苯酚；（5）甲醛、二甲胺和（a）由苯酚与三异丁烯在硫酸存在下缩合得到的十二基苯酚混合物，（b）由苯酚与四异丁烯在硫酸存在下缩合得到的十六基苯酚混合物，或（c）由苯酚与月桂醇在氯化锌存在下缩合得到的月桂基苯酚，或（d）由苯酚与月桂醇在氯化锌存在下缩合得到的十六烷基苯酚；（6）甲醛、二甲胺和α,α,γ,γ-四甲基丁基-p-甲酚；（7）甲醛、二甲胺和（a）α,α,γ,γ-四甲基丁基间苯二酚，由邻苯二酚与二异丁烯在硫酸存在下缩合得到，或（b）正己基间苯二酚。此外，通过甲醛、含有少于七个碳原子的非芳香性二级胺与苯酚相互作用，且该苯酚在核中被取代为含有三个以上碳原子的烃基，并且至少有一个自由的羟基位，可以获得基本产品。苯酚可以是单环或多环的，除了烃基外，还可以含有其他核取代基，如额外的羟基、卤素原子、烷基、烷氧基、硝基、氨基或甲醛基；醛基或自由酸基，如羧酸基或磺酸基，不得存在。烃基可以是芳香性或烷烃烃基，或者是含有三个以上碳原子的直链或支链脂肪烃基。指定的苯酚包括丁基苯酚、溴丁基苯酚、氯丁基苯酚、碘丁基苯酚，相应的戊基、己基、庚基、辛基、十二基、十六基和十八基苯酚，环己基苯酚、萜基苯酚、四氢萘基苯酚、苯基苯酚和苄基苯酚，以及相应的甲酚、间苯二酚、对羟基苯酚或萘酚衍生物。指定的二级胺包括二甲胺、二乙胺、甲乙胺、二异丙胺、二乙醇胺、二正丙胺、吡啶和哌嗪；含有一级氨基或自由酸基的二级胺的使用被排除。与水不溶酸如高级脂肪酸、萘酚酸或树脂酸的盐在油中和烃中溶解，并用作增塑剂和橡胶组合物的成分。在示例中，从以下反应中获得产品：（1）甲醛、二甲胺或二乙胺和对叔丁基苯酚、对叔戊基苯酚、对苯基苯酚或对环己基苯酚；（2）甲醛、二甲胺和邻苯基苯酚或对苯基苯酚；（3）甲醛、吡啶和α,α,γ,γ-四甲基丁基苯酚；（4）甲醛、二甲胺、二乙胺或二乙醇胺和α,α,γ,γ-四甲基丁基苯酚；（5）甲醛、二甲胺和（a）十二基苯酚混合物，（b）十六基苯酚混合物或（c）月桂基苯酚，或（d）十六烷基苯酚；（6）甲醛、二甲胺和α,α,γ,γ-四甲基丁基-p-甲酚；（7）甲醛、二甲胺和（a）α,α,γ,γ-四甲基丁基间苯二酚或（b）正己基间苯二酚。
• Aminoalkylphenols as Antimalarials. I. Simply Substituted α-Aminocresols¹
  作者：J. H. Burckhalter、F. H. Tendick、Eldon M. Jones、W. F. Holcomb、A. L. Rawlins

  DOI：10.1021/ja01214a008

  日期：1946.10
• Phenolic Invert Soaps
  作者：Joseph B. Niederl、Frank A. Abbruscato

  DOI：10.1021/ja01852a504

  日期：1941.7