methyl 4-[(2-oxocyclohexyl)carbonyl]benzoate | 1001084-39-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-[(2-oxocyclohexyl)carbonyl]benzoate
• 英文别名: methyl 4-(2-oxocyclohexanecarbonyl)benzoate；4-[(2-oxocyclohexyl)carbonyl]benzoic acid methyl ester
• CAS: 1001084-39-4
• 化学式: C₁₅H₁₆O₄
• 分子量: 260.29
• InChiKey: DLXQUPZMKIKBPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.42
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  60.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 4-[(2-oxocyclohexyl)carbonyl]benzoate 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以409 mg的产率得到4-(4,5,6,7-tetrahydro-1H-indazol-3-yl)benzoic acid methyl ester
  参考文献：
  名称：

  縮合二環式ヘテロ環誘導体

  摘要：

  提供具有优良的视黄醇酸受体相关孤儿受体γt抑制作用，并且作为银屑病等治疗药物有用的化合物。通式（Ｉ）表示的化合物或其药理上可接受的盐。【环Ａ为吡咯环、咪唑环或吡唑环；环Ｂ为取代/非取代的苯环、环己二烯环、环戊二烯环、环己烯环等；Ｒ₁为Ｈ、卤原子等；Ｒ₂为Ｈ、卤原子、Ｃ₁−Ｃ₆烷基等；基＝Ｑ−Ｔ−表示的基为基＝ＣＨ−ＣＨ＝ＣＨ−等；Ｚ为基＝ＣＨ−等；基表示为式−Ｕ−Ｖ（ＣＯ₂Ｈ）−Ｗ−的基为，基表示为式−ＣＨ＝ＣＨ−Ｃ（ＣＯ₂Ｈ）＝ＣＨ−等】【选择图】无

  公开号：

  JP2016141632A
• 作为产物：
  描述：

  对苯二甲酸单甲酯 在 草酰氯 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.83h， 生成 methyl 4-[(2-oxocyclohexyl)carbonyl]benzoate
  参考文献：
  名称：

  縮合二環式ヘテロ環誘導体

  摘要：

  提供具有优良的视黄醇酸受体相关孤儿受体γt抑制作用，并且作为银屑病等治疗药物有用的化合物。通式（Ｉ）表示的化合物或其药理上可接受的盐。【环Ａ为吡咯环、咪唑环或吡唑环；环Ｂ为取代/非取代的苯环、环己二烯环、环戊二烯环、环己烯环等；Ｒ₁为Ｈ、卤原子等；Ｒ₂为Ｈ、卤原子、Ｃ₁−Ｃ₆烷基等；基＝Ｑ−Ｔ−表示的基为基＝ＣＨ−ＣＨ＝ＣＨ−等；Ｚ为基＝ＣＨ−等；基表示为式−Ｕ−Ｖ（ＣＯ₂Ｈ）−Ｗ−的基为，基表示为式−ＣＨ＝ＣＨ−Ｃ（ＣＯ₂Ｈ）＝ＣＨ−等】【选择图】无

  公开号：

  JP2016141632A

文献信息

• Regiochemistry of the Condensation of 2-Aroyl-cyclohexanones and 2-Cyanoacetamide: ¹³C-Labeling Studies and Semiempirical MO Calculations
  作者：Oscar P. J. van Linden、Maikel Wijtmans、Luc Roumen、Lonneke Rotteveel、Rob Leurs、Iwan. J. P. de Esch

  DOI：10.1021/jo301138w

  日期：2012.9.7

  Hydroxy-aryl-5,6,7,8-tetrahydroisoquinoline-4-carbonitriles represent interesting chemical scaffolds, but synthetic access to these compounds is limited. The reaction of 2-aroyl-cyclohexanones with 2-cyanoacetamide and base in ethanol has been reported to lead to the formation of the tetrahydroisoquinoline isomer. We show that depending on the electronic nature of the para-substituent on the aryl ring, formation of the regioisomeric tetrahydroquinoline isomer can significantly compete. The electron-donating or -withdrawing properties of the para-substituent of the aryl ring determines the ratio of product isomers. A series of 2-aroyl-cyclohexanones, with para-substituents ranging from electron-donating to electron-withdrawing, were reacted with [2-C-13]-cyanoacetamide. The product ratio and absolute regiochemistry were directly determined by quantitative C-13, HMBC, and NOESY NMR spectroscopy on the reaction mixtures. A clear relationship between the regioisomeric product ratio and the Hammett sigma values of the substituents is demonstrated. This is explained by the separate in situ yields, which reveal that the pathway leading to the tetrahydroquinoline regioisomer is significantly more sensitive toward the electronic nature of the para-substituent than the pathway leading to the tetrahydroisoquinoline. Semiempirical AM1 molecular orbital calculations on the starting electrophile 2-aroyl-cyclohexanone support a correlation between the energy of the LUMOs and the regioisomeric product ratio. Our results facilitate synthetic access to a range of these interesting synthetic intermediates.
• 縮合二環式ヘテロ環誘導体
  申请人：第一三共株式会社

  公开号：JP2016141632A

  公开（公告）日：2016-08-08

  【課題】優れたレチノイン酸受容体関連オーファン受容体γｔ阻害作用を有し、乾癬等の治療薬として有用な化合物の提供。【解決手段】一般式（Ｉ）で表される化合物又はその薬理上許容される塩。［環Ａはピロール環、イミダゾール環又はピラゾール環；環Ｂは置換／非置換のベンゼン環、シクロヘキサジエン環、シクロペンテン環、シクロヘキセン環等；Ｒ１はＨ、ハロゲン原子等；Ｒ２はＨ、ハロゲン原子、Ｃ１−Ｃ６アルキル基等；式＝Ｑ−Ｔ−で表される基は式＝ＣＨ−ＣＨ＝ＣＨ−で表される基等；Ｚは式＝ＣＨ−で表される基等；式−Ｕ−Ｖ（ＣＯ２Ｈ）−Ｗ−で表される基は、式−ＣＨ＝ＣＨ−Ｃ（ＣＯ２Ｈ）＝ＣＨ−で表される基等］【選択図】なし

  提供具有优良的视黄醇酸受体相关孤儿受体γt抑制作用，并且作为银屑病等治疗药物有用的化合物。通式（Ｉ）表示的化合物或其药理上可接受的盐。【环Ａ为吡咯环、咪唑环或吡唑环；环Ｂ为取代/非取代的苯环、环己二烯环、环戊二烯环、环己烯环等；Ｒ₁为Ｈ、卤原子等；Ｒ₂为Ｈ、卤原子、Ｃ₁−Ｃ₆烷基等；基＝Ｑ−Ｔ−表示的基为基＝ＣＨ−ＣＨ＝ＣＨ−等；Ｚ为基＝ＣＨ−等；基表示为式−Ｕ−Ｖ（ＣＯ₂Ｈ）−Ｗ−的基为，基表示为式−ＣＨ＝ＣＨ−Ｃ（ＣＯ₂Ｈ）＝ＣＨ−等】【选择图】无
• Synthesis and antiplatelet activity of ethyl 4-(1-benzyl-1H-indazol-3-yl)benzoate (YD-3) derivatives
  作者：Hua-Sin Chen、Sheng-Chu Kuo、Che-Ming Teng、Fang-Yu Lee、Jih-Pyang Wang、Yu-Chun Lee、Chiung-Wen Kuo、Ching-Che Huang、Chin-Chung Wu、Li-Jiau Huang

  DOI：10.1016/j.bmc.2007.10.070

  日期：2008.2.1

  Previously, ethyl 4-(1-benzyl-1H-indazol-3-yl)benzoate (YD-3) was identified by us as the first non-peptide protease-activated receptor 4 (PAR4) antagonist. To continue on our development of novel anti-PAR4 agents, YD-3 was used as a lead compound and a series of its derivatives were synthesized and evaluated for their selective anti-PAR4 activity. Through structure-activity relationship (SAR) study, we identified the important functional groups contributing to anti-PAR4 activity, and these functional groups were kept intact during subsequent structural modification. Several new compounds with anti-PAR4 activity comparable to YD-3 were identified. Among them, ethyl 4-[1-(3-chlorobenzyl)-1H-indazol-3-yl]benzoate (33) showed the most potent inhibitory effect on PAR4-mediated platelet aggregation, ATP release, and P-selectin expression. On the other hand, ethyl 4-(1-phenyl-1H-indazol-3-yl)benzoate (83) exhibited dual inhibitory effects on PAR4 and thromboxane formation from arachidonic acid. The above findings can be used as guidelines for development of novel antiplatelet drug candidates. (c) 2008 Published by Elsevier Ltd.