4-(p-Bromphenyl)-4-dimethylaminocyclohexanon | 65619-52-5

• 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: 4-(p-Bromphenyl)-4-dimethylaminocyclohexanon
• 英文别名: 4-(p-bromophenyl)-4-dimethylaminocyclohexanone；4-(4-Bromophenyl)-4-dimethylaminocyclohexanone；4-(4-bromophenyl)-4-(dimethylamino)cyclohexan-1-one
• CAS: 65619-52-5
• 化学式: C₁₄H₁₈BrNO
• 分子量: 296.207
• InChiKey: FUNZUWAJMVRIRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(p-Bromphenyl)-4-dimethylaminocyclohexanon 、 magnesium,ethylbenzene,bromide 生成 Bdpc hydrochloride
  参考文献：
  名称：

  LEDNICER D.; VOIGTLANDER P. F. VON, J. MED. CHEM. 1979, 22, NO 10, 1157-1158

  摘要：

  DOI：
• 作为产物：
  描述：

  4-(p-bromophenyl)-4-dimethylaminocyclohexanone, ethylene ketal hydrochloride 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以69%的产率得到4-(p-Bromphenyl)-4-dimethylaminocyclohexanon
  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

文献信息

• 4-Amino-4-arylcyclohexanones and their derivatives: a novel class of analgesics. 2. Modification of the carbonyl function
  作者：Daniel Lednicer、Philip F. VonVoigtlander、D. Edward Emmert

  DOI：10.1021/jm00136a010

  日期：1981.4

  modification of the carbonyl function of analgesics derived from 4-(dimethylamino)-4-arylcyclohexan-1-one was studied by reduction and by addition of nucleophiles. The resulting amino alcohols were separated and assigned structures on the basis of X-ray crystallography, NMR, and TLC mobility. The trans (OH and N) isomers were invariably more potent than the cis. Inclusion of flat lipophilic moieties (phenyl

  通过还原和添加亲核试剂，研究了对衍生自4-（二甲氨基）-4-芳基环己-1-酮的镇痛药的羰基官能团修饰的影响。分离得到的氨基醇，并基于X射线晶体学，NMR和TLC迁移率确定结构。反式（OH和N）异构体总是比顺式更有效。在距含碳羟基至少两个碳原子的距离处包含平坦的亲脂性部分（苯基，环己烯基）导致效力增加了几个数量级。讨论了其对受体相互作用的可能意义。
• Three-Component Coupling Approach for the Synthesis of Diverse Heterocycles Utilizing Reactive Nitrilium Trapping
  作者：András Váradi、Travis C. Palmer、Paula R. Notis、Gabriel N. Redel-Traub、Daniel Afonin、Joan J. Subrath、Gavril W. Pasternak、Chunhua Hu、Indrajeet Sharma、Susruta Majumdar

  DOI：10.1021/ol500328t

  日期：2014.3.21

  The formation of an unexpected heterocyclic scaffold, a benzoxazole, in a three-component reaction between a ketone, isocyanide, and 2-aminophenol was encountered. This reaction involved a benzo[b][1,4]oxazine intermediate resulting from intramolecular attack of the aminophenol hydroxyl group on the nitrilium ion. Unlike previous literature examples, the trapped nitrilium benzo[b][1,4]oxazine could

  在酮、异氰化物和 2-氨基苯酚之间的三组分反应中，遇到了意想不到的杂环支架苯并恶唑的形成。该反应涉及苯并[ b ][1,4] 恶嗪中间体，该中间体由氨基酚羟基对腈离子的分子内攻击产生。与之前的文献实例不同，被捕获的腈基苯并[ b ][1,4]恶嗪可以很容易地与双亲核试剂进行开环。反应范围包括简单的线性以及复杂的环酮和取代的 2-氨基苯酚。具有代表性的苯并恶唑产品可以进一步多样化以产生类似药物的化合物。
• Substituted 4-aminocyclohexanols
  申请人：Gruenenthal Gmbh

  公开号：US20040236104A1

  公开（公告）日：2004-11-25

  Substituted 4-aminocyclohexanols, methods of producing the same, pharmaceuticals containing these compounds, the use of substituted 4-aminocyclohexanols for producing pharmaceutical compositions for the treatment of various indications, in particular pain, and for related treatment methods.

  替代的4-氨基环己醇，其生产方法，含有这些化合物的药物，使用替代的4-氨基环己醇制备药物组合物治疗各种适应症，特别是疼痛，并用于相关治疗方法。
• DE2839891
  申请人：——

  公开号：——

  公开（公告）日：——
• LEDNICER D.; VOIGTLANDER P. F.; EMMERT D. E., J. MED. CHEM., 1980, 23, NO 4, 424-430
  作者：LEDNICER D.、 VOIGTLANDER P. F.、 EMMERT D. E.

  DOI：——

  日期：——