4-氰基-4-(2-噻吩基)环己酮 | 65619-58-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 中文名称: 4-氰基-4-(2-噻吩基)环己酮
• 英文名称: 4-oxo-1-(thiophen-2-yl)cyclohexane-1-carbonitrile
• 英文别名: 4-Cyano-4-(thien-2-yl)cyclohexanone；4-oxo-1-thiophen-2-ylcyclohexane-1-carbonitrile
• CAS: 65619-58-1
• 化学式: C₁₁H₁₁NOS
• 分子量: 205.28
• InChiKey: ALRLCKXXSWRJQO-UHFFFAOYSA-N

物化性质

• 熔点：
  117.5-119 °C(Solv: dichloromethane (75-09-2))
• 沸点：
  391.3±42.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  69.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-氰基-4-(2-噻吩基)环己酮 在 sodium hydroxide 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 叠氮磷酸二苯酯 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 乙二醇 、 苯 为溶剂， 反应 45.0h， 生成 4-dimethylamino-4-(2-thienyl)-cyclohexanone, ethylene ketal
  参考文献：
  名称：

  4-Amino-4-arylcyclohexanones and their derivatives, a novel class of analgesics. 1. Modification of the aryl ring

  摘要：

  Investigation of central nervous system activity of phenylcyclohexylamines was continued by preparation of "reversed" analogues. Following the unexpected finding of analgesic activity with 1-(dimethylamino)-1-phenylcyclohexylamine, the SAR of the series was investigated. Synthesis starts by double Michael reaction of acrylate on arylacetonitriles. Following cyclization, decarboxylation, ketalization, and saponification, the geminally substituted acid is rearranged to the isocyanate by means of (C6H5O)2PON3. Isocyanates were then converted to the title compounds. Analgesic activity is very sensitive to the nature and position of the substitutent on the aromatic ring. The most potent compounds in this series (p-CH3, p-Br) showed 50% the potency of morphine. Deletion of the ring oxygen abolishes activity.

  DOI：

  10.1021/jm00178a014
• 作为产物：
  描述：

  ethyl 5-cyano-2-oxo-5-(thiophen-2-yl)cyclohexanecarboxylate 在 盐酸 、 水 作用下， 以 溶剂黄146 为溶剂， 反应 3.0h， 以43%的产率得到4-氰基-4-(2-噻吩基)环己酮
  参考文献：
  名称：

  Spirocyclic Azaindole Derivatives

  摘要：

  该发明涉及取代的氮杂吲哚衍生物，其制备方法，含有该化合物的药物以及使用取代的氮杂吲哚衍生物来生产药物。

  公开号：

  US20090156593A1

文献信息

• 4-Pyrrolidino-cyclohexanone ketals
  申请人：The Upjohn Company

  公开号：US04180584A1

  公开（公告）日：1979-12-25

  A class of new 4-amino-4-arylcyclohexanones, their ketals, and acid addition salts have been synthesized and found to be useful for relieving pain in animals. Their analgesic activity appears to be of high order, and in addition some exhibit narcotic antagonist activity that is useful in modifying the cardiovascular, respiratory, and behavioral depression caused by other analgesics. Several show mixed analgesic and narcotic antagonist activity. Preferred compounds of the class are 4-(m-hydroxyphenyl)-4-dimethylaminocyclohexanone ethylene ketal, and 4-(m-hydroxyphenyl)-4-(n-butylmethylamino)cyclohexanone ethylene ketal as free bases and as their hydrochloride salts. Processes for snythesis and intermediates are described. Unit dosage forms and therapeutic treatments are disclosed.

  一类新的4-氨基-4-芳基环己酮、它们的缩酮和酸加成盐已被合成并发现对缓解动物疼痛有用。它们的镇痛活性似乎是高级别的，另外一些表现出麻醉拮抗活性，有助于改变其他镇痛剂引起的心血管、呼吸和行为抑制。几种显示出混合的镇痛和麻醉拮抗活性。该类化合物的首选物是4-（间羟基苯基）-4-二甲氨基环己酮乙二醇缩酮和4-（间羟基苯基）-4-（正丁基甲基氨基）环己酮乙二醇缩酮，作为自由碱和它们的盐酸盐。描述了合成和中间体的过程。揭示了单元剂量形式和治疗方法。
• 4-Amino-4-aryl-cyclohexanones
  申请人：The Upjohn Company

  公开号：US04460604A1

  公开（公告）日：1984-07-17

  A class of 4-amine-4-arylcyclohexanones, their ketals, and acid addition salts have been synthesized and found to be useful for relieving pain in animals. Their analgesic activity appears to be of high order, and in addition some exhibit narcotic antagonist activity that is useful in modifying the cardiovascular, respiratory, and behavioral depression caused by other analgesics. Several show mixed analgesic and narcotic antagonist activity. Preferred compounds of the class are 4-(m-hydroxyphenyl)-4-dimethylaminocyclohexanone ethylene ketal, and 4-(m-hydroxyphenyl)-4-(n-butylmethylamino)cyclohexanone ethylene ketal as free bases and as their hydrochloride salts. Processes for synthesis and intermediates are described. Unit dosage forms and therapeutic treatments are disclosed.

  一类4-氨基-4-芳基环己酮及其缩酮和酸加成盐已经被合成，并发现它们对动物缓解疼痛非常有用。它们的镇痛活性似乎是很高的，此外，一些化合物还表现出镇痛拮抗活性，对于调节其他镇痛药物引起的心血管、呼吸和行为抑制非常有用。几种化合物显示出混合的镇痛和镇痛拮抗活性。该类化合物中的优选化合物是4-(间羟基苯基)-4-二甲氨基环己酮乙烯缩酮和4-(间羟基苯基)-4-(正丁基甲基氨基)环己酮乙烯缩酮，作为自由碱和它们的盐酸盐。描述了合成和中间体的过程。公制剂量形式和治疗方法也被披露。
• 4-Amino-4-phenylcyclohexanone ketal compositions and process of use
  申请人：The Upjohn Company

  公开号：US04065573A1

  公开（公告）日：1977-12-27

  A class of new 4-amino-4-arylcyclohexanones, their ketals, and acid addition salts have been synthesized and found to be useful for relieving pain in animals. Their analgesic activity appears to be of high order, and in addition some exhibit narcotic antagonist activity that is useful in modifying the cardiovascular, respiratory, and behavioral depression caused by other analgesics. Several show mixed analgesic and narcotic antagonist activity. Preferred compounds of the class are 4-(m-hydroxyphenyl)-4-dimethylaminocyclohexanone ethylene ketal, and 4-(m-hydroxyphenyl)-4-(n-butylmethylamino)cyclohexanone ethylene ketal as free bases and as their hydrochloride salts. Processes for synthesis and intermediates are described. Unit dosage forms and therapeutic treatments are disclosed.

  一类新的4-氨基-4-芳基环己酮、它们的缩醛和酸加成盐已经被合成，并被发现在动物止痛方面有用。它们的镇痛活性似乎是高级别的，另外一些表现出镇痛拮抗剂活性，这对于改变其他镇痛药物引起的心血管、呼吸和行为抑制是有用的。其中一些表现出混合的镇痛和镇痛拮抗剂活性。该类化合物的首选物是4-(间羟基苯基)-4-二甲氨基环己酮乙烯缩醛，以及4-(间羟基苯基)-4-(正丁基甲基氨基)环己酮乙烯缩醛，作为自由碱和它们的盐酸盐。描述了合成和中间体的过程。揭示了单元剂量形式和治疗方法。
• CYCLOALKYL INHIBITORS OF POTASSIUM CHANNEL FUNCTION
  申请人：Lloyd John

  公开号：US20070142333A1

  公开（公告）日：2007-06-21

  Novel cycloalkyl compounds useful as inhibitors of potassium channel function (especially inhibitors of the K v 1 subfamily of voltage gated K + channels, especially inhibitors K v 1.5 which has been linked to the ultra-rapidly activating delayed rectifier K + current I Kur ), methods of using such compounds in the prevention and treatment of arrhythmia and I Kur -associated conditions, and pharmaceutical compositions containing such compounds.

  新型环烷基化合物可作为钾通道功能抑制剂使用（特别是钾离子电压门控K+通道的Kv1亚家族的抑制剂，特别是与超快速激活延迟整流K+电流IKur相关的Kv1.5抑制剂），使用这种化合物预防和治疗心律失常和IKur相关疾病的方法，以及含有这种化合物的药物组合物。
• Spirocyclic azaindole derivatives
  申请人：Zemolka Saskia

  公开号：US08399503B2

  公开（公告）日：2013-03-19

  The invention relates to substituted azaindole derivatives, to methods for the production thereof, to medicaments containing said compounds and to the use of substituted azaindole derivatives for producing medicaments.

  本发明涉及取代的氮杂吲哚衍生物，其制备方法，含有该化合物的药物以及使用取代的氮杂吲哚衍生物制备药物的用途。