4-氰基-4-(2-氯苯基)环己酮 | 65618-88-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-氰基-4-(2-氯苯基)环己酮
• 英文名称: 4-(o-Chlorphenyl)-4-cyano-cyclohexanon
• 英文别名: 4-(o-chlorophenyl)-4-cyanocyclohexanone；1-cyano-1-(2-chlorophenyl)cyclohexan-4-one；1-(2-Chlorophenyl)-4-oxocyclohexanecarbonitrile；1-(2-chlorophenyl)-4-oxocyclohexane-1-carbonitrile
• CAS: 65618-88-4
• 化学式: C₁₃H₁₂ClNO
• 分子量: 233.697
• InChiKey: BIMOIQNSDSBDDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  4-氰基-4-(2-氯苯基)环己酮 在 sodium hydroxide 、 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 36.0h， 生成 4-(o-chlorophenyl)-4-methylaminocyclohexanone, 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：

  邻氯苯乙腈 在 硫酸 、 potassium tert-butylate 、 四甲基氢氧化铵 、 溶剂黄146 作用下， 生成 4-氰基-4-(2-氯苯基)环己酮
  参考文献：
  名称：

  DE2723937

  摘要：

  公开号：

文献信息

• [EN] SUBSTITUTED ISOQUINOLINES AND ISOQUINOLINONES AS RHO KINASE INHIBITORS<br/>[FR] ISOQUINOLINES ET ISOQUINOLINONES SUBSTITUÉES UTILISÉES COMME INHIBITEURS DE RHO-KINASE
  申请人：SANOFI AVENTIS

  公开号：WO2009156100A1

  公开（公告）日：2009-12-30

  The invention relates to substituted isoquinoline and isoquinolinones of the formula (I) useful for the treatment and/or prevention of diseases associated with Rho-kinase and/or Rho-kinase mediated phosphorylation of myosin light chain phosphatase, and compositions containing such compounds.

  该发明涉及用于治疗和/或预防与Rho激酶和/或Rho激酶介导的肌球蛋白轻链磷酸酶磷酸化相关疾病的配方(I)的取代异喹啉和异喹啉酮，以及含有这种化合物的组合物。
• 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-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。
• SUBSTITUTED ISOQUINOLINES AND ISOQUINOLINONES AS RHO KINASE INHIBITORS
  申请人：Plettenburg Oliver

  公开号：US20110190341A1

  公开（公告）日：2011-08-04

  The invention relates to substituted isoquinoline and isoquinolinones of the formula (I) useful for the treatment and/or prevention of diseases associated with Rho-kinase and/or Rho-kinase mediated phosphorylation of myosin light chain phosphatase, and compositions containing such compounds.

  本发明涉及公式（I）的取代异喹啉和异喹啉酮，用于治疗和/或预防与Rho激酶和/或Rho激酶介导的肌球蛋白轻链磷酸酶的磷酸化相关的疾病，以及含有这些化合物的组合物。
• Potent bradykinin B1 receptor antagonists: 4-Substituted phenyl cyclohexanes
  作者：Dai-Shi Su、John L. Lim、M. Kristine Markowitz、Bang-Lin Wan、Kathy L. Murphy、Duane R. Reiss、C. Meacham Harrell、Stacy S. O’Malley、Rick W. Ransom、Raymond S.L. Chang、Douglas J. Pettibone、Cuyue Tang、Thomayant Prueksaritanont、Roger M. Freidinger、Mark G. Bock

  DOI：10.1016/j.bmcl.2007.03.059

  日期：2007.6

  Selective bradykinin (BK) B-1 receptor antagonists have been shown to be antinociceptive in animal models and could be novel therapeutic agents for the treatment of pain and inflammation. Elucidation of the structure-activity relationships of the biphenyl moiety of the lead compound 1 provided a potent new structural class of BK B-1 receptor antagonists. (C) 2007 Elsevier Ltd. All rights reserved.