2-cyclohexyl-N-methoxy-N-methylacetamide | 134560-43-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-cyclohexyl-N-methoxy-N-methylacetamide
• CAS: 134560-43-3
• 化学式: C₁₀H₁₉NO₂
• mdl: MFCD18839891
• 分子量: 185.266
• InChiKey: ZGQFRAVROHICNI-UHFFFAOYSA-N

物化性质

• 沸点：
  243.8±23.0 °C(Predicted)
• 密度：
  0.986±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-cyclohexyl-N-methoxy-N-methylacetamide 在 甲烷磺酸 、 palladium on carbon 、 氢溴酸 、 potassium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 正庚烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 20.0~75.0 ℃ 、230.0 kPa 条件下， 反应 1.67h， 生成 3-环己基-2-(2-羟苯基)-1H-吲哚-6-羧酸甲酯
  参考文献：
  名称：

  An Efficient Process for the Large-Scale Synthesis of a 2,3,6-Trisubstituted Indole

  摘要：

  The efficient synthesis of a key trisubstituted indole intermediate 1 is described. The synthetic route required the use of an aryl Grignard reagent which was not commercially available, and the large-scale formation of this fragment and the thermal evaluation for this step is presented. The key step in the sequence was a Truce-Smiles rearrangement to provide an advanced ketone intermediate which, upon reduction, cyclized to the desired indole 1. Design of experiment (DoE) optimization of this reduction is also presented. In total >50 kg of target indole 1 were synthesized in 55% overall yield over five steps using this new route.

  DOI：

  10.1021/op300303p
• 作为产物：
  描述：

  环己基乙酸 在 草酰氯 、 N,N-二异丙基乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 2-cyclohexyl-N-methoxy-N-methylacetamide
  参考文献：
  名称：

  改善 HCV NS5B 聚合酶非核苷变构抑制剂的复制子细胞活性：从苯并咪唑到吲哚支架。

  摘要：

  基于苯并咪唑的丙型肝炎病毒 (HCV) NS5B 聚合酶变构抑制剂被多样化用于各种拓扑相关的支架。用亲脂性吲哚取代极性苯并咪唑核心导致抑制剂在基于细胞的亚基因组 HCV 复制子系统中具有更高的效力。将吲哚支架转移到先前描述的一系列苯并咪唑-色氨酸酰胺中产生了迄今为止在该系列中报告的细胞培养物中最有效的 HCV RNA 复制抑制剂（EC(50) 约 50 nM）。

  DOI：

  10.1016/j.bmcl.2006.07.074

文献信息

• ‘Wake-Up Call of A Sleeping Beauty’: Straightforward Synthesis of Functionalized β-(2-Pyridyl) Ketones from 2,6-Lutidine
  作者：Laure Bouchez、Cyril Gerbeaux、Marion Rusch、Maude Patoor、Madeleine Livendahl、Neil Press

  DOI：10.1055/s-0036-1588154

  日期：2017.6

  β-(2-Pyridyl) ketones are a unique class of heterocycles with valuable physicochemical properties and emerging relevance as pharmacophores. Herein we report a one-step process for the preparation of various substituted β-(2-pyridyl) ketones from the common starting material, 2,6-lutidine. Furthermore, we demonstrate the utility of this building block by synthesizing of a small set of antimalarial natural

  β-(2-吡啶基) 酮是一类独特的杂环化合物，具有有价值的理化性质和作为药效团的新兴相关性。在本文中，我们报告了一种从常见起始材料 2,6-二甲基吡啶制备各种取代 β-(2-吡啶基) 酮的一步法。此外，我们通过合成一小组抗疟天然产物来证明该构件的实用性。
• A Weinreb amide approach to the synthesis of trifluoromethylketones
  作者：DiAndra M. Rudzinski、Christopher B. Kelly、Nicholas E. Leadbeater

  DOI：10.1039/c2cc35037h

  日期：——

  A novel route to access trifluoromethylketones (TFMKs) from Weinreb amides is reported. This represents the first documented case of the Ruppert–Prakash reagent (TMS–CF3) reacting in a constructive manner with an amide and enables synthesis of TMFKs without risk of over-trifluoromethylation.

  报道了一条从Weinreb酰胺制备三氟甲基酮（TFMKs）的新路线。这是首次记录到Ruppert–Prakash试剂（TMS–CF3）以建设性方式与酰胺反应，并且可以无需担心过度三氟甲基化风险地合成TMFKs。
• Structure-based design of six novel classes of nonpeptide antagonists of the bradykinin B2 receptor
  作者：Dean R Artis、Christine Brotherton-Pleiss、Joseph H.B Pease、Clara J Lin、Steve W Ferla、Sherry R Newman、Sunil Bhakta、Helene Ostrelich、Kurt Jarnagin

  DOI：10.1016/s0960-894x(00)00482-0

  日期：2000.11

  Six classes of nonpeptide bradykinin antagonists were designed using a template derived from structural studies of peptide antagonists. Several compounds from each class were synthesized and assayed for binding to the human bradykinin B2 receptor. Each family showed compounds active at the level of the smallest template peptide; three classes contained compounds with Kd < 8 microM. These results provide

  使用衍生自肽拮抗剂结构研究的模板设计了六类非肽缓激肽拮抗剂。合成了每种类别的几种化合物，并测定了与人缓激肽B2受体的结合。每个家族均显示出在最小模板肽水平上具有活性的化合物。三类含有Kd <8 microM的化合物。这些结果为基于药物化学的优化程序提供了多种线索。
• Pharmacologically active phenylalkanoyl substituted imidazo (4,5-C)
  申请人：G. D. Searle & Co.

  公开号：US04988707A1

  公开（公告）日：1991-01-29

  This invention relates to substituted imidazopyridine dervatives having the following formula ##STR1## and isomers thereof; or a pharmaceutically acceptable acid addition salt thereof: wherein R.sub.1 and R.sub.2 are each independently selected from hydrogen; straight or branched chain alkyl of 1 to 15 carbon atoms; cycloalkyl of 3 to 8 carbon atoms; cycloalkyl which can be substituted once or more by alkyl of 1 to 6 carbon atoms; phenyl; phenyl which can be substituted once or more by alkyl of 1 to 6 carbon atoms or halogen; straight or branched alkenyl having 3 to 15 carbon atoms. y is phenyl or phenyl substituted once or more by alkyl of 1 to 6 carbon atoms; alkoxy wherein the alkyl is 1 to 6 carbon atoms; and halogen selected from the group consisting of bromo, fluoro or chloro. m is an integer from 0 to 5. n is an integer from 1 to 5. R.sub.3 is a group substituted at one or more of the 4, 6 or 7 positions of the pyridine ring said groups being independently selected from hydrogen, alkyl of 1 to 6 carbon atoms; halogen wherein the halogen is selected from bromo, fluoro, or chloro; or alkoxy wherein the alkyl is 1 to 6 carbon atoms; R.sub.4 is hydrogen or alkyl of 1 to 4 carbon atoms. useful in the treatment of diseases or disorders mediated by platelet-activating factor. This invention also relates to pharmaceutical compositions of such substituted imidazopyridines.

  本发明涉及具有以下结构的替代咪唑吡啶衍生物 ##STR1## 及其异构体；或其药学上可接受的酸盐：其中R.sub.1和R.sub.2各自独立选择自氢；1至15个碳原子的直链或支链烷基；3至8个碳原子的环烷基；可被1至6个碳原子的烷基取代一次或多次的环烷基；苯基；可被1至6个碳原子的烷基或卤素取代一次或多次的苯基；具有3至15个碳原子的直链或支链烯基。y是苯基或可被1至6个碳原子的烷基取代一次或多次的苯基；烷氧基，其中烷基是1至6个碳原子；以及溴、氟或氯等卤素中选择的卤素。m是从0到5的整数。n是从1到5的整数。R.sub.3是取代在吡啶环的4、6或7位置的一个或多个基团，这些基团独立选择自氢、1至6个碳原子的烷基；卤素，其中卤素选择自溴、氟或氯；或烷氧基，其中烷基是1至6个碳原子；R.sub.4是氢或1至4个碳原子的烷基。用于治疗由血小板活化因子介导的疾病或紊乱。本发明还涉及这类替代咪唑吡啶的药物组合物。
• Iridium(I)-Catalyzed Intramolecular Hydrocarbonation of Alkenes: Efficient Access to Cyclic Systems Bearing Quaternary Stereocenters
  作者：David F. Fernández、Moisés Gulías、José L. Mascareñas、Fernando López

  DOI：10.1002/anie.201705105

  日期：2017.8.1

  wide variety of cyclic systems featuring methyl-substituted quaternary stereocenters is described. The method relies on the use of a cationic IrI–bisphosphine catalyst, which promotes a carboxamide-assisted activation of an olefinic C(sp2)−H bond followed by exo-cyclization to a tethered 1,1-disubstituted alkene. The extension of the method to aromatic and heteroaromatic C−H bonds, as well as developments

  描述了一种催化，多功能且原子经济的CH功能化过程，该过程提供了多种以甲基取代的季位立体中心为特征的环状系统。该方法依赖于使用阳离子Ir I-双膦催化剂，该催化剂可促进羧酰胺辅助的烯烃C（sp 2）-H键的活化，然后外环化成束缚的1，1-二取代的烯烃。还介绍了该方法对芳族和杂芳族CH键的扩展以及对映选择性变体的开发。