1-(4-methoxyphenylamino)cyclohexanecarbonitrile | 70441-14-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(4-methoxyphenylamino)cyclohexanecarbonitrile
• 英文别名: 1-<4-Methoxy-anilino>-cyclohexan-carbonsaeure-(1)-nitril；1-p-Anisidino-cyclohexancarbonitril；1-(4-Methoxyanilino)cyclohexane-1-carbonitrile
• CAS: 70441-14-4
• 化学式: C₁₄H₁₈N₂O
• mdl: MFCD02247116
• 分子量: 230.31
• InChiKey: LPPFXMNSDKCUPN-UHFFFAOYSA-N

物化性质

• 沸点：
  230-232 °C(Press: 20 mmHg)
• 密度：
  1.09±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)
• 溶解度：
  12.4 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  45
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-methoxyphenylamino)cyclohexanecarbonitrile 在 盐酸 、 硫酸 、 溶剂黄146 、 乙二胺 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 72.0h， 生成 1-(4-methoxyphenyl)-1,4-diazaspiro[5.5]undecane-3,5-dione
  参考文献：
  名称：

  新型 1-((2-羟乙基)(芳基)氨基)-N-取代的环烷烃甲酰胺及其乙酸酯的合成、分子建模研究和抗惊厥评价

  摘要：

  设计并合成了一系列 1-((2-羟乙基)(芳基)氨基)-N-取代的环烷烃甲酰胺 IXa-l 及其乙酸酯 Xa-l 作为新型抗惊厥剂。通过皮下戊四唑 (scPTZ) 和小鼠最大电休克 (MES) 试验在体内进行抗惊厥作用的评估。此外，确定了神经毒性、肝毒性和急性毒性。在剂量范围为 0.0057–0.283 mmol/kg 的 scPTZ 屏幕中，所有新候选药物都显示出 100% 的抗惊厥活性。scPTZ 筛选中最有效的化合物是 Xh (ED50 = 0.0012 mmol/kg)、Xd (ED50 = 0.002 mmol/kg)、Xf (ED50 = 0.004 mmol/kg)、IXj (ED50 = 0.0047 mmol/kg)、Xl (ED50 = 0.0076 mmol/kg) 和 Xi (ED50 = 0.008 mmol/kg)。它们在抗惊厥潜力方面表现出比黄金标准更高的倍数活性，苯巴比妥和乙琥胺。化合物

  DOI：

  10.1002/ardp.201800269
• 作为产物：
  描述：

  环己酮 在 ammonium hydroxide 作用下， 以 水 为溶剂， 生成 1-(4-methoxyphenylamino)cyclohexanecarbonitrile
  参考文献：
  名称：

  Transamination of α-amino nitriles

  摘要：

  alpha-Amino nitriles containing a primary amino group undergo transamination with aliphatic and aromatic amines under mild conditions with high yields. A probable reaction mechanism involving intermediate elimination of cyanide ion has been proposed.

  DOI：

  10.1134/s1070428014010047

文献信息

• Solvent-free three component Strecker reaction of ketones using highly recyclable and hydrophobic sulfonic acid based nanoreactors
  作者：Babak Karimi、Daryoush Zareyee

  DOI：10.1039/b911388f

  日期：——

  An efficient and environmentally benign system was developed for the one-pot three-component Strecker reaction of ketones under solvent-free conditions, with the use of a highly recoverable SBA-15 supported sulfonic acid. Also findings concerning the effects of functionalized inert groups and silica backbone pore size on substrate scope, catalytic activity and recycling behavior of the catalysts were briefly discussed. The simple experimental and product isolation procedure accompanied by easy recovery and reusability of the catalyst could be considered as attractive features of this new protocol which will hopefully develop a clean strategy for the synthesis of α-amino nitriles.

  通过使用高回收率的 SBA-15 支承磺酸，开发出了一种高效且对环境无害的系统，用于在无溶剂条件下进行酮类化合物的一锅三组分 Strecker 反应。此外，还简要讨论了官能化惰性基团和二氧化硅骨架孔径对底物范围、催化活性和催化剂回收行为的影响。实验和产物分离过程简单，催化剂易于回收和重复使用，这些都是这一新方案的诱人之处，有望为 α-氨基腈的合成开发出一种清洁的策略。
• Exploring new cyclohexane carboxamides based GABA agonist: Design, synthesis, biological evaluation, in silico ADME and docking studies
  作者：Walaa Hamada Abd-Allah、Mostafa Abd El-Mohsen Anwar、Eman R. Mohammed、Marawan A. Elbaset、Samir M. El Moghazy

  DOI：10.1016/j.bioorg.2023.106561

  日期：2023.7

  toxicity and the estimates for LD50 were stated. Further neurochemical study was performed to investigate the effect of the most active compounds in ScPTZ test on GABA level in brain of the mice; a significant elevation in GABA level was obvious for compound 6d compared to control group confirming GABAergic modulating activity. Docking study was accomplished to examine the binding interaction of the newly

  使用“金标准方法”ScPTZ 和 MES 模型、神经毒性、肝酶和神经化学测定，设计、合成并测试了新系列的5a-e、6a-e和7a-e衍生物的抗惊厥活性。合成类似物的筛选表现出可变的抗惊厥潜力，尤其是在化学诱发的癫痫发作中。定量研究表明，化合物6d和6e是最有效的类似物，在 ScPTZ 试验中的ED 50分别为 44.77 和 11.31 mg/kg。化合物6e(0.031 mmol/kg) 比苯巴比妥 (0.056 mmol/kg) 强约 2 倍，比作为参考标准药物的乙琥胺 (0.92 mmol/kg) 强 30 倍。此外，所有合成的化合物都使用旋转杆法筛选急性神经毒性以识别运动损伤，而除了化合物5a、5b、7a和7e之外的所有化合物都没有神经毒性。对最活跃的化合物进行了急性毒性检查，并说明了LD 50的估计值。进行了进一步的神经化学研究，以研究 ScPTZ 试验中最活跃的化合物对小鼠大脑中
• Substituted spirocyclic inhibitors of autotaxin
  申请人：X-Rx, Inc.

  公开号：US10011601B2

  公开（公告）日：2018-07-03

  The present invention relates to compounds according to Formula 1 and pharmaceutically acceptable salts, synthesis, intermediates, formulations, and methods of disease treatment therewith, including cancer, lymphocyte homing, chronic inflammation, neuropathic pain, fibrotic diseases, thrombosis, and cholestatic pruritus, mediated at least in part by ATX.

  本发明涉及根据式 1 的化合物和药学上可接受的盐、合成、中间体、制剂以及用其治疗疾病的方法，包括至少部分由 ATX 介导的癌症、淋巴细胞归巢、慢性炎症、神经性疼痛、纤维化疾病、血栓形成和胆汁淤积性瘙痒症。
• Magnetic Solid Sulfonic Acid Decorated with Hydrophobic Regulators: A Combinatorial and Magnetically Separable Catalyst for the Synthesis of α-Aminonitriles
  作者：Akbar Mobaraki、Barahman Movassagh、Babak Karimi

  DOI：10.1021/co500022g

  日期：2014.7.14

  A three-component, Strecker reaction of a series of aldehydes or ketones, amines, and trimethylsilyl cyanide for the synthesis of alpha-aminonitriles in the presence of a catalytic amount of a magnetic solid sulfonic acid catalyst, Fe3O4@SiO2@Me&Et-PhSO3H under solvent-free conditions have been investigated. This catalyst, with a combination of hydrophobicity and acidity on the Fe3O4@SiO2 core-shell of the magnetic nanobeads, as well as its water-resistant property, enabled easy mass transfer and catalytic activity in the Strecker reaction. The catalyst was easily separated by an external magnet and the recovered catalyst was reused in 6 successive reaction cycles without any significant loss of activity.
• SUBSTITUTED SPIROCYCLIC INHIBITORS OF AUTOTAXIN
  申请人：X-RX, INC.

  公开号：US20170166568A1

  公开（公告）日：2017-06-15

  The present invention relates to compounds according to Formula 1 and pharmaceutically acceptable salts, synthesis, intermediates, formulations, and methods of disease treatment therewith, including cancer, lymphocyte homing, chronic inflammation, neuropathic pain, fibrotic diseases, thrombosis, and cholestatic pruritus, mediated at least in part by ATX.