N-(2,6-dimethylphenyl)cyclohexanecarboxamide | 315712-17-5

• 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: N-(2,6-dimethylphenyl)cyclohexanecarboxamide
• 英文别名: Cyclohexanecarboxylic acid (2,6-dimethyl-phenyl)-amide
• CAS: 315712-17-5
• 化学式: C₁₅H₂₁NO
• 分子量: 231.338
• InChiKey: JLNUFNBCQJGFTL-UHFFFAOYSA-N

物化性质

• 沸点：
  375.2±11.0 °C(Predicted)
• 密度：
  1.063±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(2,6-dimethylphenyl)cyclohexanecarboxamide 在 五氯化磷 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 N-(2,6-dimethylphenyl)cyclohexanecarboximidoyl chloride
  参考文献：
  名称：

  亚氨基酰氯作为制备掩蔽的酰基锂中间体的原料：合成应用

  摘要：

  通过亚化学计量的萘催化几种亚氨基酰氯5的锂化，然后与不同的亲电试剂反应，在水解后，根据反应条件，得到相应的亚胺衍生物6和9或胺7。通过用稀盐酸（对于N-芳基衍生物）或用硅胶（对于N-烷基衍生物）处理，将亚胺衍生物容易地转化成相应的酮。得到的羟基亚胺与LiAlH 4反应，得到相应的1，2-氨基醇，为单一的非对映异构体。当亚胺部分在原位时，发现相同的结果用锂还原。得到的1,2-氨基醇很容易转变成相应的1,3-恶唑烷11通过与反应段在酸性催化下-甲醛。

  DOI：

  10.1016/s0040-4020(98)83054-8
• 作为产物：
  描述：

  环己甲酸 在 吡啶 、 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 2.0h， 生成 N-(2,6-dimethylphenyl)cyclohexanecarboxamide
  参考文献：
  名称：

  Synthesis and structure–activity relationships of potential anticonvulsants based on 2-piperidinecarboxylic acid and related pharmacophores

  摘要：

  Using N-(2,6-dimethyl)phenyl-2-piperidinecarboxamide (1) and N-(alpha -methylbenzyl)-2-piperidinecarboxamide (2) as structural leads, a variety of analogues were synthesised and evaluated for anticonvulsant activity in the MES test in mice. In the N-benzyl series, introduction of 3-Cl, 4-Cl, 3,4-Cl-2, or 3-CF3 groups on the aromatic ring led to an increase in MES activity. Replacement of the alpha -methyl group by either i-Pr or benzyl groups enhanced MES activity with no increase in neurotoxicity. Substitution on the piperidine ring nitrogen led to a decrease in MES activity and neurotoxicity, while reduction of the amide carbonyl led to a complete loss of activity. Movement of the carboxamide group to either the 3- or 4-positions of the piperidine ring decreased MES activity and neurotoxicity. Incorporation of the piperidine ring into a tetrahydroisoquinoline or diazahydrinone nucleus led to increased neurotoxicity. In the N-(2,6-dimethyl)phenyl series, opening of the piperidine ring between the 1- and 6-positions gave the active norleucine derivative 75 (ED50 = 5.8 mg kg(-1), TD50 = 36.4 mg kg(-1), PI = 6.3). Replacement of the piperidine ring of I by cycloalkane (cyclohexane, cyclopentane, and cyclobutane) resulted in compounds with decreased MES activity and neurotoxicity, whereas replacement of the piperidine ring by a 4-pyridyl group led to a retention of MES activity with a comparable PI. Simplification of the 2-piperidinecarboxamide nucleus of 1 into a glycinecarboxamide nucleus led to about a six-fold decrease in MES activity. The 2,6-dimethylanilides were the most potent compounds in the MES test in each group of compounds evaluated, and compounds 50 and 75 should be useful leads in the development of agents for the treatment of tonic-clonic and partial seizures in man. (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)01206-x

文献信息

• Copper‐Promoted Oxidative Amidation of Imines: A Facile Route to Amides
  作者：Zhonghua Cao、Da Sheng、Zhiyang Zhang、Haitao Ren、Yong Liu、Songhai Wu、Jiaxiang Zhang、Xu Han

  DOI：10.1002/ejoc.202400315

  日期：——

  A method for preparing amides by imines oxidation is developed using aldehydes and amines as raw materials. Using copper oxide as catalyst and Oxone as oxidant without any coupling reagents, the reaction conditions are mild. A wide substrate range including pesticide and drug molecules has been demonstrated in 32–90 % yields.

  开发了一种以醛和胺为原料，亚胺氧化制备酰胺的方法。以氧化铜为催化剂，Oxone为氧化剂，不使用任何偶联剂，反应条件温和。包括农药和药物分子在内的多种底物已被证明具有 32-90% 的产率。
• Synthesis and structure–activity relationships of potential anticonvulsants based on 2-piperidinecarboxylic acid and related pharmacophores
  作者：Bin Ho、A Michael Crider、James P Stables

  DOI：10.1016/s0223-5234(00)01206-x

  日期：2001.3

  Using N-(2,6-dimethyl)phenyl-2-piperidinecarboxamide (1) and N-(alpha -methylbenzyl)-2-piperidinecarboxamide (2) as structural leads, a variety of analogues were synthesised and evaluated for anticonvulsant activity in the MES test in mice. In the N-benzyl series, introduction of 3-Cl, 4-Cl, 3,4-Cl-2, or 3-CF3 groups on the aromatic ring led to an increase in MES activity. Replacement of the alpha -methyl group by either i-Pr or benzyl groups enhanced MES activity with no increase in neurotoxicity. Substitution on the piperidine ring nitrogen led to a decrease in MES activity and neurotoxicity, while reduction of the amide carbonyl led to a complete loss of activity. Movement of the carboxamide group to either the 3- or 4-positions of the piperidine ring decreased MES activity and neurotoxicity. Incorporation of the piperidine ring into a tetrahydroisoquinoline or diazahydrinone nucleus led to increased neurotoxicity. In the N-(2,6-dimethyl)phenyl series, opening of the piperidine ring between the 1- and 6-positions gave the active norleucine derivative 75 (ED50 = 5.8 mg kg(-1), TD50 = 36.4 mg kg(-1), PI = 6.3). Replacement of the piperidine ring of I by cycloalkane (cyclohexane, cyclopentane, and cyclobutane) resulted in compounds with decreased MES activity and neurotoxicity, whereas replacement of the piperidine ring by a 4-pyridyl group led to a retention of MES activity with a comparable PI. Simplification of the 2-piperidinecarboxamide nucleus of 1 into a glycinecarboxamide nucleus led to about a six-fold decrease in MES activity. The 2,6-dimethylanilides were the most potent compounds in the MES test in each group of compounds evaluated, and compounds 50 and 75 should be useful leads in the development of agents for the treatment of tonic-clonic and partial seizures in man. (C) 2001 Editions scientifiques et medicales Elsevier SAS.
• Imidoyl chlorides as starting materials for the preparation of masked acyllithium intermediates: synthetic applications
  作者：Emma Alonso、Diego J. Ramón、Miguel Yus

  DOI：10.1016/s0040-4020(98)83054-8

  日期：1998.9

  The lithiation of several imidoyl chlorides 5, catalysed by substoichiometric amounts of naphthalene, followed by reaction with different electrophiles gives, after hydrolysis, the corresponding imine derivatives 6 and 9 or amines 7, depending on the reaction conditions. The imine derivatives are easily converted into the corresponding ketones by treatment either with dilute hydrochloric acid, for

  通过亚化学计量的萘催化几种亚氨基酰氯5的锂化，然后与不同的亲电试剂反应，在水解后，根据反应条件，得到相应的亚胺衍生物6和9或胺7。通过用稀盐酸（对于N-芳基衍生物）或用硅胶（对于N-烷基衍生物）处理，将亚胺衍生物容易地转化成相应的酮。得到的羟基亚胺与LiAlH 4反应，得到相应的1，2-氨基醇，为单一的非对映异构体。当亚胺部分在原位时，发现相同的结果用锂还原。得到的1,2-氨基醇很容易转变成相应的1,3-恶唑烷11通过与反应段在酸性催化下-甲醛。