7-bromo-6,7-dihydro-8(5H)-quinolinone | 137234-14-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 7-bromo-6,7-dihydro-8(5H)-quinolinone
• 英文别名: 7-bromo-6,7-dihydro-5H-quinolin-8-one
• CAS: 137234-14-1
• 化学式: C₉H₈BrNO
• 分子量: 226.073
• InChiKey: PWAHHUYVRBAPAB-UHFFFAOYSA-N

物化性质

• 沸点：
  335.2±42.0 °C(Predicted)
• 密度：
  1.610±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 3,3-diaminoacrylate 、 7-bromo-6,7-dihydro-8(5H)-quinolinone 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 2-amino-4,5-dihydro-1H-pyrrolo<3,2-h>quinoline-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Enolate complexation in acetonitrile with a neutral polyaza cleft

  摘要：

  DOI：

  10.1021/ja00025a052
• 作为产物：
  描述：

  8-(tert-butyldimethylsiloxy)-5,6-dihydroquinoline 在 pyridinium hydrobromide perbromide 、 溶剂黄146 作用下， 反应 12.0h， 以54%的产率得到7-bromo-6,7-dihydro-8(5H)-quinolinone
  参考文献：
  名称：

  Molecular Recognition of Enolates of Active Methylene Compounds in Acetonitrile. The Interplay between Complementarity and Basicity and the Use of Hydrogen Bonding to Lower Guest pKas

  摘要：

  A model system for enolase and racemase enzymes was used to explore the extent to which traditional hydrogen bonds can increase carbon acidity. Polyazaclefts 1 and 2 were investigated as receptors for active methylene enolates 10 to 19 in acetonitrile. Receptor 1 was designed to form four hydrogen bonds to the heteroatoms of the enolate guests. The synthesis of the receptors began with the central pyridine ring followed by formation of the peripheral pyrrole rings. Binding constants for 1 with the enolates 10 to 17 in acetonitrile vary from 1.75 x 10(2) to 2.72 x 10(4) M(-1). The nature of both the enolate functionality and the counterion were found to affect the strength of complexation. Molecular mechanics and X-ray analysis of host 1 were used to predict the geometries of the guest-host complexes. Nonaqueous titrations with picric acid were performed on enolates 10 to 17 in order to assess the degree to which complexation was changed by the basicity of the enolate, Complementarity of the guest to host 1 was found to be the dominant factor in enolate binding and not guest basicity. However, a correlation was found to exist between basicity and binding for enolates of the same shape and functionality. Binding by host 1 was found to increase the acidity of 1,3-cyclohexanedione by 1.0 pK(a) unit in acetonitrile. Therefore, traditional hydrogen bonds exert only enough anion stabilization to account for a small fraction of the large pK(a) shifts found for enolase and racemase enzymes. Nevertheless, this acidity increase can be exploited as a means to induce deprotonation of 1,3-cyclohexanedione in the presence of 1.

  DOI：

  10.1021/ja00117a013

文献信息

• [EN] NOVEL MICROBIOCIDAL DIOXIME ETHER DERIVATIVES<br/>[FR] NOUVEAUX DÉRIVÉS MICROBICIDES D'ÉTHER DE DIOXIME
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2012001040A1

  公开（公告）日：2012-01-05

  The present invention provides compounds of formula (I) wherein R1, A1, X, Y6, Y7, Y8, G1, G2, G3 and p are as defined in the claims. The invention further provides intermediates used in the preparation of these compounds, to compositions which comprise these compounds and to their use in agriculture or horticulture for controlling or preventing infestation of plants by phytopathogenic microorganisms, preferably fungi.

  本发明提供了以下式（I）的化合物，其中R1、A1、X、Y6、Y7、Y8、G1、G2、G3和p如权利要求中所定义。本发明还提供了用于制备这些化合物的中间体，以及包含这些化合物的组合物，并将其用于农业或园艺中，以控制或预防植物受植物病原微生物，尤其是真菌的侵害。
• NOVEL MICROBIOCIDAL DIOXIME ETHER DERIVATIVES
  申请人：Nebel Kurt

  公开号：US20130102631A1

  公开（公告）日：2013-04-25

  The present invention provides compounds of formula (I) wherein R 1 , A 1 , X, Y 6 , Y 7 , Y 8 , G 1 , G 2 , G 3 and p are as defined in the claims. The invention further provides intermediates used in the preparation of these compounds, to compositions which comprise these compounds and to their use in agriculture or horticulture for controlling or preventing infestation of plants by phytopathogenic microorganisms, preferably fungi.

  本发明提供公式(I)中的化合物，其中R1，A1，X，Y6，Y7，Y8，G1，G2，G3和p如权利要求书所定义。本发明还提供用于制备这些化合物的中间体，包括这些化合物的组合物以及它们在农业或园艺中用于控制或预防植物被植物病原微生物，优选为真菌侵染。
• [EN] BENZENE RING COMPOUND AND USE THEREOF<br/>[FR] COMPOSÉ CYCLIQUE BENZÉNIQUE ET SON UTILISATION<br/>[ZH] 一种苯环类化合物及其应用
  申请人：NANJING SHIJIANG MEDICINE TECH CO LTD

  公开号：WO2022127923A1

  公开（公告）日：2022-06-23

  本发明涉及一种苯环类化合物及其应用。具体地，本发明提供一种式I化合物、或其光学异构体或其外消旋体、或其溶剂化物、或其药学上可接受的盐。本发明所述的化合物对肿瘤具有优异的治疗效果。
• Enolate complexation in acetonitrile with a neutral polyaza cleft
  作者：Anne M. Kelly-Rowley、Larry A. Cabell、Eric V. Anslyn

  DOI：10.1021/ja00025a052

  日期：1991.12
• Molecular Recognition of Enolates of Active Methylene Compounds in Acetonitrile. The Interplay between Complementarity and Basicity and the Use of Hydrogen Bonding to Lower Guest pKas
  作者：Anne M. Kelly-Rowley、Vincent M. Lynch、Eric V. Anslyn

  DOI：10.1021/ja00117a013

  日期：1995.3

  A model system for enolase and racemase enzymes was used to explore the extent to which traditional hydrogen bonds can increase carbon acidity. Polyazaclefts 1 and 2 were investigated as receptors for active methylene enolates 10 to 19 in acetonitrile. Receptor 1 was designed to form four hydrogen bonds to the heteroatoms of the enolate guests. The synthesis of the receptors began with the central pyridine ring followed by formation of the peripheral pyrrole rings. Binding constants for 1 with the enolates 10 to 17 in acetonitrile vary from 1.75 x 10(2) to 2.72 x 10(4) M(-1). The nature of both the enolate functionality and the counterion were found to affect the strength of complexation. Molecular mechanics and X-ray analysis of host 1 were used to predict the geometries of the guest-host complexes. Nonaqueous titrations with picric acid were performed on enolates 10 to 17 in order to assess the degree to which complexation was changed by the basicity of the enolate, Complementarity of the guest to host 1 was found to be the dominant factor in enolate binding and not guest basicity. However, a correlation was found to exist between basicity and binding for enolates of the same shape and functionality. Binding by host 1 was found to increase the acidity of 1,3-cyclohexanedione by 1.0 pK(a) unit in acetonitrile. Therefore, traditional hydrogen bonds exert only enough anion stabilization to account for a small fraction of the large pK(a) shifts found for enolase and racemase enzymes. Nevertheless, this acidity increase can be exploited as a means to induce deprotonation of 1,3-cyclohexanedione in the presence of 1.