N-Cyclohexyl-N'-benzoyl-hydrazin | 1211-63-8

• 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-Cyclohexyl-N'-benzoyl-hydrazin
• 英文别名: n'-Cyclohexylbenzohydrazide
• CAS: 1211-63-8
• 化学式: C₁₃H₁₈N₂O
• 分子量: 218.299
• InChiKey: PSEGQGAZPYBNLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-Cyclohexyl-N'-benzoyl-hydrazin 在 potassium carbonate 作用下， 以 丁酮 为溶剂， 反应 4.0h， 生成 2-phenyl-4-cyclohexyl-4H-1,3,4-oxadiazine-5(6H)-one
  参考文献：
  名称：

  Discovery of 2-(2-Oxo-1-phenyl-5-pyridin-2-yl-1,2-dihydropyridin-3-yl)benzonitrile (Perampanel): A Novel, Noncompetitive α-Amino-3-hydroxy-5-methyl-4-isoxazolepropanoic Acid (AMPA) Receptor Antagonist

  摘要：

  Dysfunction of glutamatergic neurotransmission has been implicated in the pathogenesis of epilepsy and numerous other neurological diseases. Here we describe the discovery of a series of 1,3,5-triaryl-1H-pyridin-2-one derivatives as noncompetitive antagonists of AMPA-type ionotropic glutamate receptors. The structure-activity relationships for this series of compounds were investigated by manipulating individual aromatic rings located at positions 1, 3, and 5 of the pyridone ring. This culminated in the discovery of 2-(2-oxo-1-phenyl-5-pyridin-2-yl-1,2-dihydropyridin-3-yl) benzonitrile (perampanel, 6), a novel, noncompetitive AMPA receptor antagonist that showed potent activity in an in vitro AMPA-induced Ca2+ influx assay (IC50 = 60 nM) and in an in vivo AMPA-induced seizure model (minimum effective dose of 2 mg/kg po). Perampanel is currently in regulatory submission for partial-onset seizures associated with epilepsy.

  DOI：

  10.1021/jm301268u
• 作为产物：
  描述：

  苯甲羟肟酸 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 N-Cyclohexyl-N'-benzoyl-hydrazin
  参考文献：
  名称：

  Convenient Syntheses of 1-Acyl-2-alkylhydrazines

  摘要：

  使用 2-Cloro-1-methylpyridinium iodide 2 或对甲苯磺酰氯 3 从羟肟酸 1 和胺 6 中制备出 1-酰基-2-烷基肼 7，收率为 27-68%。

  DOI：

  10.1055/s-1987-27883

文献信息

• Direct Catalytic Symmetrical, Unsymmetrical N,N-Dialkylation and Cyclization of Acylhydrazides Using Alcohols
  作者：Subramanian Thiyagarajan、Chidambaram Gunanathan

  DOI：10.1021/acs.orglett.0c02369

  日期：2020.8.21

  Herein, direct N,N-dialkylation of acylhydrazides using alcohols is reported. This catalytic protocol provides one-pot synthesis of both symmetrical and unsymmetrical N,N-disubstituted acylhydrazides using an assortment of primary and secondary alcohols with remarkable selectivity and excellent yields. Interestingly, the use of diols resulted in intermolecular cyclization of acylhydrazides, and such

  在本文中，报道了使用醇将酰肼直接进行N，N-二烷基化。该催化方案使用各种伯醇和仲醇，具有显着的选择性和优异的收率，可以一锅法合成对称和不对称的N，N-二取代的酰肼。有趣的是，使用二醇导致酰肼的分子间环化，并且此类产物是生物活性化合物中的优先结构。水是唯一的副产物，这使得该催化方案可持续且对环境无害。
• RUBBER COMPOSITION AND PNEUMATIC TIRES
  申请人：Bridgestone Corporation

  公开号：EP0909788A1

  公开（公告）日：1999-04-21

  A rubber composition prepared by compounding 0.05 to 20 parts by weight of at least one selected from substituted hydrazide compounds represented by the following Formulas (I) to (IV) per 100 parts by weight of a rubber component comprising at least one rubber selected from the group consisting of natural rubber and synthetic rubber, and a pneumatic tire using the same: wherein A represents one selected from the group consisting of an aromatic group which may have a substituent, a hydantoin ring which may have a substituent, and a saturated or unsaturated linear hydrocarbon having 1 to 18 carbon atoms; Y represents hydrogen, an amino group, an alkyl group having 1 to 18 carbon atoms, a cycloalkyl group, an alkenyl group, an aromatic group, a pyridyl group or hydrazino group; and R1 to R11 each represent hydrogen, an alkyl group having 1 to 18 carbon atoms, a cycloalkyl group or an aromatic group.

  一种橡胶组合物，其制备方法是每 100 重量份由至少一种选自天然橡胶和合成橡胶组的橡胶组成的橡胶组分中混入 0.05 至 20 重量份的至少一种选自下式(I)至(IV)所代表的取代酰肼化合物，以及使用该组合物的充气轮胎： 其中 A 代表选自芳香基团（可具有取代基）、海因环（可具有取代基）和具有 1 至 18 个碳原子的饱和或不饱和线性烃；Y 代表氢、氨基、具有 1 至 18 个碳原子的烷基、环烷基、烯基、芳香基、吡啶基或肼基；R1 至 R11 分别代表氢、具有 1 至 18 个碳原子的烷基、环烷基或芳香基。
• Rubber composition and pneumatic tire
  申请人：Bridgestone Corporation

  公开号：EP1420044A2

  公开（公告）日：2004-05-19

  A hydrazone derivative represented by Formula (V):         ZC(=O)NHN=C(CH3) (CH2CH(CH3)2)     (V) wherein Z represents 3-hydroxy-2-naphthyl, 1-hydroxy-2-naphthyl, 2-hydroxyphenyl or 2,6-dihydroxyphenyl group.

  式 (V) 所代表的腙衍生物： ZC(=O)NHN=C(CH3) (CH2CH( )2) (V) 其中 Z 代表 3-羟基-2-萘基、1-羟基-2-萘基、2-羟基苯基或 2,6-二羟基苯基。
• OKAWARA TADASHI; KANAZAWA YASUNORI; YAMASAKI TETSUO; FURUKAWA MITSURU, SYNTHESIS,(1987) N 2, 183-184
  作者：OKAWARA TADASHI、 KANAZAWA YASUNORI、 YAMASAKI TETSUO、 FURUKAWA MITSURU

  DOI：——

  日期：——
• US6013836A
  申请人：——

  公开号：US6013836A

  公开（公告）日：2000-01-11