N-(4-Methoxyphenyl)-1-adamantanecarboxamide | 42600-89-5

• 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-(4-Methoxyphenyl)-1-adamantanecarboxamide
• 英文别名: adamantan-1-carboxylic acid (4-methoxyphenyl)amide；N-(4-methoxyphenyl)adamantane-1-carboxamide；N-p-methoxyphenyl-1-adamantanecarboxamide；N-(4-Methoxyphenyl)-1-adamantancarboxamid
• CAS: 42600-89-5
• 化学式: C₁₈H₂₃NO₂
• mdl: MFCD01790074
• 分子量: 285.386
• InChiKey: DOMQVXNITFPQNL-UHFFFAOYSA-N

物化性质

• 熔点：
  178-179 °C
• 沸点：
  474.4±28.0 °C(Predicted)
• 密度：
  1.205±0.06 g/cm3(Predicted)
• 保留指数：
  2611

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4-Methoxyphenyl)-1-adamantanecarboxamide 在 4-二甲氨基吡啶 、 三氯化磷 作用下， 反应 1.0h， 以97%的产率得到N-(4-methoxyphenyl)adamantane-1-carboximidoyl chloride
  参考文献：
  名称：

  三氯化磷合成亚氨酰氯

  摘要：

  摘要 在 4-二甲氨基吡啶催化剂存在下，羧酰胺与三氯化磷在 75-80°C 下加热反应 1 小时，用于合成亚胺酰氯，产率为 63-99%。

  DOI：

  10.1134/s1070428021050134
• 作为产物：
  描述：

  2-金刚烷甲酸 、 甲氧苯胺 在 N,N-二乙基-1,1,2,3,3,3-六氟丙胺 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以92%的产率得到N-(4-Methoxyphenyl)-1-adamantanecarboxamide
  参考文献：
  名称：

  Method for preparing some 1-adamantancecarboxamides

  摘要：

  该发明涉及一种新颖的制备1-金刚烷甲酰胺和1-金刚烷乙酰胺的方法。通过将金刚烷甲酸和金刚烷乙酸与N,N-二乙基-1,1,2,3,3,3-六氟丙胺处理，然后加入水氨或适当的胺，可以高产率（80-100%）地制备金刚烷甲酰胺和金刚烷乙酰胺。该程序在常温下使用常见实验室设备进行，既方便又快速，只需一两个小时。可以同时进行几个反应。

  公开号：

  US06348625B1

文献信息

• Substituted aryl and aralkyl amides in the treatment of parkinsonism
  申请人：Schering Corporation

  公开号：US03944675A1

  公开（公告）日：1976-03-16

  Amides having aromatic substituents of the formula: ##SPC1## Wherein R is an acyl radical derived from a carboxylic acid having from 3 to 20 carbon atoms, X and Y are members selected from the group consisting of hydrogen, fluoro, trifluoromethyl and hydroxy, and n is an integer selected from the group consisting of 0, 1 and 2, exhibit an effect upon the central nervous system.

  含有芳香基团的酰胺的化学式为：##SPC1## 其中，R是从含有3至20个碳原子的羧酸衍生的酰基，X和Y是从氢、氟、三氟甲基和羟基组成的成员中选择的，n是从0、1和2组成的整数中选择的，对中枢神经系统产生影响。
• Substituted aryl and aralkyl amides
  申请人：Schering Corporation

  公开号：US04053509A1

  公开（公告）日：1977-10-11

  Amides having aromatic substituents of the formula: ##STR1## wherein R is an acyl radical derived from a carboxylic acid having from 3 to 20 carbon atoms, X and Y are members selected from the group consisting of hydrogen, fluoro, trifluoromethyl and hydroxy, and n is an integer selected from the group consisting of 0, 1 and 2, exhibit an effect upon the central nervous system.

  具有芳香基取代基的酰胺的化学式为：##STR1## 其中R是来自具有3至20个碳原子的羧酸的酰基基团，X和Y是从氢，氟，三氟甲基和羟基组成的成员中选择的，n是从0，1和2组成的整数，表现出对中枢神经系统的影响。
• NOVEL ADAMANTANE DERIVATIVE COMPOUND
  申请人：Amorepacific Corporation

  公开号：EP3187486A1

  公开（公告）日：2017-07-05

  Disclosed is a novel adamantine derivative compound, an isomer thereof, pharmaceutically acceptable salt thereof, prodrug thereof, hydrate thereof or a solvate thereof. Also disclosed is a method for preparing a novel adamantine derivative compound, an isomer thereof, pharmaceutically acceptable salt thereof, prodrug thereof, hydrate thereof or a solvate thereof. The novel adamantane derivative compound or the like has an excellent anti-androgenic effect.

  公开了一种新型金刚烷衍生物化合物、其异构体、其药学上可接受的盐、其原药、其水合物或其溶液。还公开了一种制备新型金刚烷衍生物化合物、其异构体、其药学上可接受的盐、其原药、其水合物或其溶液的方法。新型金刚烷衍生物化合物或类似物具有优异的抗雄激素作用。
• Adamantane derivative compound
  申请人：AMOREPACIFIC CORPORATION

  公开号：US10696611B2

  公开（公告）日：2020-06-30

  Disclosed is a novel adamantine derivative compound, an isomer thereof, pharmaceutically acceptable salt thereof, prodrug thereof, hydrate thereof or a solvate thereof. Also disclosed is a method for preparing a novel adamantine derivative compound, an isomer thereof, pharmaceutically acceptable salt thereof, prodrug thereof, hydrate thereof or a solvate thereof. The novel adamantane derivative compound or the like has an excellent anti-androgenic effect.

  公开了一种新型金刚烷衍生物化合物、其异构体、其药学上可接受的盐、其原药、其水合物或其溶液。还公开了一种制备新型金刚烷衍生物化合物、其异构体、其药学上可接受的盐、其原药、其水合物或其溶液的方法。新型金刚烷衍生物化合物或类似物具有优异的抗雄激素作用。
• Structure−Activity Relationships of Cycloalkylamide Derivatives as Inhibitors of the Soluble Epoxide Hydrolase
  作者：In-Hae Kim、Yong-Kyu Park、Bruce D. Hammock、Kosuke Nishi

  DOI：10.1021/jm101431v

  日期：2011.3.24

  Structure-activity relationships of cycloalkylamide compounds as inhibitors of human sEH were investigated. When the left side of amide function was modified by a variety of cycloalkanes, at least a C6 like cyclohexane was necessary to yield reasonable inhibition potency on the target enzyme. In compounds with a smaller cycloalkane or with a polar group on the left side of amide function, no inhibition was observed. On the other hand, increased hydrophobicity dramatically improved inhibition potency. Especially, a tetrahydronaphthalene (20) effectively increased the potency. When a series of alkyl or aryl derivatives of cycloalkylamide were investigated to continuously optimize the right side of the amide pharmacophore, a benzyl moiety functionalized with a polar group produced highly potent inhibition. A nonsubstituted benzyl, alkyl, aryl, or biaryl structure present on the right side of the cycloalkylamide function induced a big decrease in inhibition potency. Also, the resulting potent cycloalkylamide (32) showed reasonable physical properties.