N-(4-bromophenyl)-2-oxocyclopentane-1-carboxamide | 91844-16-5

• 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: N-(4-bromophenyl)-2-oxocyclopentane-1-carboxamide
• 英文别名: 2-Oxocyclopentancarbonsaeure-p-bromanilid；2-oxo-cyclopentanecarboxylic acid-(4-bromo-anilide)；2-Oxo-cyclopentancarbonsaeure-(4-brom-anilid)
• CAS: 91844-16-5
• 化学式: C₁₂H₁₂BrNO₂
• 分子量: 282.137
• InChiKey: JQCLAWHBAIHSJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.76
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.17
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-(4-bromophenyl)-2-oxocyclopentane-1-carboxamide 在 四(三苯基膦)钯 氢氧化钾 、 potassium carbonate 作用下， 以 乙醇 、 二甲基亚砜 、 甲苯 为溶剂， 反应 12.0h， 生成 3-(5-ethyl-4-oxo-2,3,4,5-tetrahydro-1H-cyclopenta[c]quinolin-8-yl)-4-trifluoromethoxybenzaldehyde
  参考文献：
  名称：

  RXR–LXR heterodimer modulators for the potential treatment of dyslipidemia

  摘要：

  A number of RXR agonists were synthesized and screened in functional assays. The synthesis and tile structure-activity relationship (SAR) within the series of compounds will be presented. Some in vivo data in rodent models for dyslipidemia and diabetes will also be presented. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2007.01.047
• 作为产物：
  描述：

  N-(1-环戊烯基)吗啉 、 4-溴异氰酸苯酯 生成 N-(4-bromophenyl)-2-oxocyclopentane-1-carboxamide
  参考文献：
  名称：

  RXR–LXR heterodimer modulators for the potential treatment of dyslipidemia

  摘要：

  A number of RXR agonists were synthesized and screened in functional assays. The synthesis and tile structure-activity relationship (SAR) within the series of compounds will be presented. Some in vivo data in rodent models for dyslipidemia and diabetes will also be presented. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2007.01.047

文献信息

• A Chiral Phenanthroline Ligand with a Hydrogen-Bonding Site: Application to the Enantioselective Amination of Methylene Groups
  作者：Rajasekar Reddy Annapureddy、Christian Jandl、Thorsten Bach

  DOI：10.1021/jacs.0c02803

  日期：2020.4.22

  of various quinolones and pyridones. The C-H activation reaction proceeded with high site- and enantioselectivity (14 examples, 83-97% ee). Key to its success is the use of a chiral phenanthroline ligand that is attached via an ethynyl linker to the 8-position of octahy-dro-1H-4,7-methanoisoindol-1-one. AgPF6 (10 mol%) served as the silver source, PhI=NNs as the nitrene precursor and 1,10- phenanthroline

  据报道，在各种喹诺酮类和吡啶酮类的脂肪族 C3 取代基上发生了银催化的胺化。CH 活化反应以高位点和对映选择性进行（14 个实例，83-97% ee）。其成功的关键是使用手性菲咯啉配体，该配体通过乙炔基接头连接到八氢-1H-4,7-methanoisoindol-1-one 的 8 位。AgPF6 (10 mol%) 作为银源，PhI=NNs 作为氮烯前体，1,10-菲咯啉作为配体。反应结果可以通过假设在氢键银络合物中插入氮烯 CH 来理解，其中单个 CH 键暴露于催化反应中心。
• Construction of Complex 1,3-Cyclohexadienes via Phosphine-Catalyzed (4 + 2) Annulations of δ-Acetoxy Allenoates and Ketones
  作者：Yuwen Zhang、Xiaofeng Tong

  DOI：10.1021/acs.orglett.7b02787

  日期：2017.10.6

  The phosphine-catalyzed substrate-dependent (4 + 2) annulations of δ-acetoxy allenoates with ketones is described. Allenoates 1 with an alkyl substituent at δC are able to react with cyclic 1,3-diketones 2, wherein the δC is attacked by the methenyl carbon of 2 while the αC attacks the ketone of 2. Allenoates 5 with an aryl group at δC is poised to react with cyclic β-carbonyl amides 6, in which the

  描述了膦催化的δ-乙酰氧基烯丙酸酯与酮的底物依赖性（4 + 2）环。在δC处具有烷基取代基的脲基甲酸酯1能够与环状1,3-二酮2反应，其中δC受到2的亚甲基碳的攻击，而αC侵袭2的酮。可以与环状β-羰基酰胺6反应，其中αC受到6的亚甲基碳的攻击，而δC经过1,2加成至6的酮。
• Usual and unusual reactions of cyclohexane-1,2-dione with aryl azides and amines: a structural corrigendum
  作者：Neeraj Singh、Klaus Banert

  DOI：10.1039/c6nj03835b

  日期：——

  The reported syntheses of alleged functionalised 1,2,3-triazines from cyclohexane-1,2-dione and aryl azides, in the presence of pyrrolidine and other amines, were repeated. The products do not contain the bicyclic triazine and bicyclic ketone moieties; instead, cyclohexane-fused 4,5-dihydro-1,2,3-triazoles and monocyclic β-ketoamides were obtained, respectively. These corrections are well supported

  重复报道的在吡咯烷和其他胺存在下由环己烷-1,2-二酮和芳基叠氮化物合成所谓的官能化的1,2,3-三嗪的过程。该产品不含双环三嗪和双环酮部分；取而代之的是，分别获得了环己烷稠合的4,5-二氢-1,2,3-三唑和单环β-酮酰胺。通过对NMR光谱，IR光谱，元素分析以及与先前已在文献中发表的数据进行仔细分析，很好地支持了这些校正。讨论了用于观察化合物合成的合适机理。
• Transition-Metal-Free α-Arylation of β-Keto Amides via an Interrupted Insertion Reaction of Arynes
  作者：Kishor Mohanan、Yoann Coquerel、Jean Rodriguez

  DOI：10.1021/ol302180v

  日期：2012.9.7

  Direct alpha-arylation reactions of secondary beta-keto amides with arynes, generated by fluoride-induced elimination of ortho-silyl aryltriflates, are described. The transformation proceeds via an interrupted insertion reaction of arynes and leads to densely functionalized aromatic compounds exhibiting a chiral 'all carbon' quaternary center under transition-metal-free conditions. An organocatalytic asymmetric version of the reaction also proved possible, affording the proof of concept that arynes can be involved in enantioselective transformations.
• Barany; Pianka, Journal of the Chemical Society, 1947, p. 1420
  作者：Barany、Pianka

  DOI：——

  日期：——