4-(3,5-dimethoxyphenyl)cyclohexan-1-one | 1297474-29-3

• 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-(3,5-dimethoxyphenyl)cyclohexan-1-one
• 英文别名: 4-(3,5-dimethoxyphenyl)cyclohexanone；4-(3,5-Dimethoxyphenyl)cyclohexan-1-one
• CAS: 1297474-29-3
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: XPZCDKHIJBMRJT-UHFFFAOYSA-N

物化性质

• 沸点：
  372.1±42.0 °C(Predicted)
• 密度：
  1.089±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(3,5-dimethoxyphenyl)cyclohexan-1-one 在 哌啶 、 盐酸 、 四氯苯醌 、 sulfur 作用下， 以 1,4-二氧六环 、 乙醇 、 正丁醇 为溶剂， 反应 17.0h， 生成 7-(3,5-dimethoxyphenyl)-2,3-dihydrobenzo[4,5]thieno[2,3-d]pyrrolo[1,2-a]pyrimidine-1,10-dione
  参考文献：
  名称：

  Aryl extensions of thienopyrimidinones as fibroblast growth factor receptor 1 kinase inhibitors

  摘要：

  Optimization of thienopyrimidinone derivatives as FGFR1 kinase inhibitors is being pursued. The present results confirm predictions of computational modeling that an aryl substituent can be introduced at the 2-position in structure 3. The substituent is anticipated to project deeper into the binding site and provide opportunities for enhanced activity and selectivity. The most potent analog reported herein, 13, has a 4-hydroxyphenyl substituent and yields an IC(50) of 6 mu M for inhibition of phosphorylation by FGFR1 kinase. It was also found that the western anisole-containing substituent in 3 can be replaced by a propionic acid group with no loss in potency and with potentially significant gains in pharmacologically relevant properties. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.12.081
• 作为产物：
  描述：

  1,4-二氧杂螺[4.5]癸-7-烯-8-基三氟甲磺酸酯 在 bis-triphenylphosphine-palladium(II) chloride 、 四(三苯基膦)钯 、 iron(III) chloride hexahydrate 、 palladium 10% on activated carbon 、 potassium phenolate 、 氢气 、 palladium diacetate 、 sodium carbonate 、 三苯基膦 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 丙酮 、 甲苯 为溶剂， 反应 41.5h， 生成 4-(3,5-dimethoxyphenyl)cyclohexan-1-one
  参考文献：
  名称：

  新型小分子CCR2拮抗剂的设计与合成：4-氨基哌啶衍生物的评价

  摘要：

  鉴定了新型的人CCR2趋化因子受体拮抗剂N-（2-氧代-2-（哌啶-4-基氨基）乙基）-3-（三氟甲基）苯甲酰胺系列。利用基于已知CCR2拮抗剂的药效团模型，设计了一种新的核心支架，合成了其类似物，并进行了结构亲和性研究，得出了一种新的高亲和力CCR2拮抗剂N-（2-（（1-（4-（3-（3-甲氧基苯基） ）环己基）哌啶-4-基）氨基）-2-氧代乙基）-3-（三氟甲基）苯甲酰胺。

  DOI：

  10.1016/j.bmcl.2014.10.060

文献信息

• The Catalytic Asymmetric Fischer Indolization
  作者：Steffen Müller、Matthew J. Webber、Benjamin List

  DOI：10.1021/ja2092163

  日期：2011.11.23

  The first catalytic asymmetric Fischer indolization is reported. In the presence of a 5 mol % loading of a novel spirocyclic chiral phosphoric acid, 4-substituted cyclohexanone-derived phenylhydrazones undergo a highly enantioselective indolization. Efficient catalyst turnover was achieved by the addition of a weakly acidic cation exchange resin, which removes the generated ammonia. The reaction can

  报道了第一个催化不对称 Fischer 吲哚化反应。在 5 mol% 负载的新型螺环手性磷酸的存在下，4-取代的环己酮衍生的苯腙经历高度对映选择性的吲哚化。通过添加弱酸性阳离子交换树脂，去除产生的氨，实现了有效的催化剂周转。该反应可以在温和的条件下进行，并以通常高的收率得到各种 3-取代的四氢咔唑。
• Design and synthesis of novel small molecule CCR2 antagonists: Evaluation of 4-aminopiperidine derivatives
  作者：M. Vilums、A.J.M. Zweemer、S. Dekkers、Y. Askar、H. de Vries、J. Saunders、D. Stamos、J. Brussee、L.H. Heitman、A.P. IJzerman

  DOI：10.1016/j.bmcl.2014.10.060

  日期：2014.12

  )ethyl)-3-(trifluoromethyl)benzamide series of human CCR2 chemokine receptor antagonists was identified. With a pharmacophore model based on known CCR2 antagonists a new core scaffold was designed, analogues of it synthesized and structure–affinity relationship studies derived yielding a new high affinity CCR2 antagonist N-(2-((1-(4-(3-methoxyphenyl)cyclohexyl)piperidin-4-yl)amino)-2-oxoethyl)-3-(

  鉴定了新型的人CCR2趋化因子受体拮抗剂N-（2-氧代-2-（哌啶-4-基氨基）乙基）-3-（三氟甲基）苯甲酰胺系列。利用基于已知CCR2拮抗剂的药效团模型，设计了一种新的核心支架，合成了其类似物，并进行了结构亲和性研究，得出了一种新的高亲和力CCR2拮抗剂N-（2-（（1-（4-（3-（3-甲氧基苯基） ）环己基）哌啶-4-基）氨基）-2-氧代乙基）-3-（三氟甲基）苯甲酰胺。
• Aryl extensions of thienopyrimidinones as fibroblast growth factor receptor 1 kinase inhibitors
  作者：Anil R. Ekkati、Valsan Mandiyan、Krishna P. Ravindranathan、Jae H. Bae、Joseph Schlessinger、William L. Jorgensen

  DOI：10.1016/j.tetlet.2010.12.081

  日期：2011.4

  Optimization of thienopyrimidinone derivatives as FGFR1 kinase inhibitors is being pursued. The present results confirm predictions of computational modeling that an aryl substituent can be introduced at the 2-position in structure 3. The substituent is anticipated to project deeper into the binding site and provide opportunities for enhanced activity and selectivity. The most potent analog reported herein, 13, has a 4-hydroxyphenyl substituent and yields an IC(50) of 6 mu M for inhibition of phosphorylation by FGFR1 kinase. It was also found that the western anisole-containing substituent in 3 can be replaced by a propionic acid group with no loss in potency and with potentially significant gains in pharmacologically relevant properties. (C) 2010 Elsevier Ltd. All rights reserved.