4-cyano-4-(m-methoxyphenyl)cyclohexanone | 13225-34-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-cyano-4-(m-methoxyphenyl)cyclohexanone
• 英文别名: 1-(3-methoxyphenyl)-4-oxocyclohexanecarbonitrile；1-(3-Methoxy-phenyl)-4-oxo-cyclohexan-1-carbonitril；4-(m-Anisyl)-4-cyano-cyclohexanon；1-cyano-1-(3-methoxyphenyl)cyclohexan-4-one；1-(3-methoxyphenyl)-4-oxocyclohexane-1-carbonitrile
• CAS: 13225-34-8
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: PGWABZTWFQGEOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  4-cyano-4-(m-methoxyphenyl)cyclohexanone 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 8-(3-methoxyphenyl)-N-methyl-1,4-dioxaspiro[4.5]decan-8-amine
  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：

  3-甲氧基苯乙腈 在 水 、 sodium hydride 作用下， 以 氘代二甲亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成 4-cyano-4-(m-methoxyphenyl)cyclohexanone
  参考文献：
  名称：

  EP1736467

  摘要：

  公开号：

文献信息

• 4-Aryl-4-aminocyclohexanones and their derivatives, a novel class of analgesics. 3. m-Hydroxyphenyl derivatives
  作者：Daniel Lednicer、Philip F. Von Voigtlander、D. Edward Emmert

  DOI：10.1021/jm00135a019

  日期：1981.3

  reaction the displacement of cyanide from the alpha-aminonitrile of 1,4-cyclohexanedione ketal, with the THP ether of m-hydroxyphenylmagnesium bromide. A number of the products show narcotic antagonist activity. Amino alcohols obtained on reaction of the free ketones with phenethyl Grignard reagents are potent analgetics, though devoid of antagonist activity. Systematic variation of the substituent on nitrogen

  通过将氰化物从1,4-环己二酮缩酮的α-氨基腈中置换得到的THP作为关键反应，获得了被间羟基取代的4-芳基-4-（二甲基氨基）环己-1-酮的衍生物间羟基苯基溴化镁的醚。许多产品显示出麻醉拮抗剂活性。尽管没有拮抗活性，但游离酮与苯乙基格利雅试剂的反应获得的氨基醇是有效的镇痛药。氮上取代基的系统变化显示出非经典的结构-活性关系；二甲氨基基团是最有效的拮抗剂。
• Novel piperidine derivative
  申请人：Ban Hitoshi

  公开号：US20070078120A1

  公开（公告）日：2007-04-05

  The invention provides a compound of the following formula (1): wherein m, n, and p are independently an integer of 0-4, provided 3≦m+n≦8; X is nitrogen atom or a group of the formula: C—R 15 ; Y is a substituted or unsubstituted aromatic group, etc.; R 15 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are hydrogen atom, a substituted or unsubstituted alkyl group, etc.; and Z is hydrogen atom, cyano group, etc., or a prodrug thereof, or a pharmaceutically acceptable salt thereof, which exhibits an action for enhancing LDL receptor expression, and is useful as a medicament for treating hyperlipidemia, atherosclerosis, etc.

  本发明提供了以下式(1)的化合物：其中m，n和p分别是0-4的整数，满足3≦m+n≦8；X是氮原子或式：C—R15的基团；Y是取代或未取代的芳香基团等；R15，R1，R2，R3，R4，R5，R6和R7是氢原子，取代或未取代的烷基等；Z是氢原子，氰基等，或其前药，或其药学上可接受的盐，具有增强LDL受体表达的作用，并且可用作治疗高脂血症，动脉粥样硬化等药物。
• Novel Sulfonamide derivative
  申请人：Ban Hitoshi

  公开号：US20080096922A1

  公开（公告）日：2008-04-24

  A compound of the formula (1): wherein m, n and p is independently an integer of 0 to 4 with the proviso that 3≦m+n≦8; X is the formula: NR 4 , etc.; R 1 , R 3 and R 4 are a substituted or unsubstituted aryl group, etc.; R 2 is a hydrogen atom, etc.; a, b, c, d, e and f are a hydrogen atom or a substituted or unsubstituted alkyl group, etc.; Y is the formula: —SO 2 —, etc.; and Z is an oxygen atom, etc.; or a prodrug thereof or a pharmaceutically acceptable salt of the same has an activity of potentiating an expression of a low density lipoprotein receptor and thus is useful as an agent for treating hyperlipidemia or arteriosclerosis.

  公式（1）的化合物： 其中，m，n和p分别为0至4的整数，但须满足3≦m+n≦8；X为公式：NR4等；R1，R3和R4为取代或未取代的芳基基团等；R2为氢原子等；a，b，c，d，e和f为氢原子或取代或未取代的烷基基团等；Y为公式：—SO2—等；Z为氧原子等；或其前体药物或其药学上可接受的盐具有增强低密度脂蛋白受体表达的活性，因此可用作治疗高脂血症或动脉硬化的药物。
• 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。
• NOVEL PIPERIDINE DERIVATIVE
  申请人：Dainippon Sumitomo Pharma Co., Ltd.

  公开号：EP1679069A1

  公开（公告）日：2006-07-12

  The invention provides a compound of the following formula (1): wherein m, n, and p are independently an integer of 0 - 4, provided 3 ≤ m + n ≤ 8; X is nitrogen atom or a group of the formula: C-R15; Y is a substituted or unsubstituted aromatic group, etc.; R15, R1, R2, R3, R4 , R5, R6 and R7 are hydrogen atom, a substituted or unsubstituted alkyl group, etc.; and Z is hydrogen atom, cyano group, etc., or a prodrug thereof, or a pharmaceutically acceptable salt thereof, which exhibits an action for enhancing LDL receptor expression, and is useful as a medicament for treating hyperlipidemia, atherosclerosis, etc.

  本发明提供了下式（1）的化合物： 其中m、n和p独立地为0-4的整数，条件是3≤m+n≤8；X为氮原子或式中的基团：C-R15；Y 是取代或未取代的芳香基等；R15、R1、R2、R3、R4、R5、R6 和 R7 是氢原子、取代或未取代的烷基等；Z 是氢原子、氰基等、 或其原药或其药学上可接受的盐，具有增强低密度脂蛋白受体表达的作用，可作为治疗高脂血症、动脉粥样硬化等的药物。

表征谱图