(7-Hydroxy-8-methyl-2-oxochromen-4-yl) 4-methylbenzenesulfonate | 219784-11-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: (7-Hydroxy-8-methyl-2-oxochromen-4-yl) 4-methylbenzenesulfonate
• CAS: 219784-11-9
• 化学式: C₁₇H₁₄O₆S
• 分子量: 346.361
• InChiKey: YDHRQRWGQMNVIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  98.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (7-Hydroxy-8-methyl-2-oxochromen-4-yl) 4-methylbenzenesulfonate 在 palladium diacetate 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 5-Methyl-1H-pyrrole-2-carboxylic acid (2S,3R,4S,5S,6S)-2-{4-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-8-methyl-2-oxo-2H-chromen-7-yloxy}-3-hydroxy-5-methoxy-6-methyl-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Tosylates in palladium-catalysed coupling reactions. Application to the synthesis of arylcoumarin inhibitors of gyrase B

  摘要：

  The palladium-catalysed coupling reaction between tosylate derivatives and organostannanes has been investigated as a methodology for carbon-carbon bond formation. Aryl substituents have been successfully incorporated even in highly functionalised coumarin structures to afford new analogues of the antibiotic novobiocin. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02351-5
• 作为产物：
  描述：

  4,7-dihydroxy-8-methyl-2H-1-benzopyran-2-one 、 对甲苯磺酰氯 在 吡啶 作用下， 反应 2.0h， 生成 Toluene-4-sulfonic acid 4-hydroxy-8-methyl-2-oxo-2H-chromen-7-yl ester 、 (7-Hydroxy-8-methyl-2-oxochromen-4-yl) 4-methylbenzenesulfonate
  参考文献：
  名称：

  Tosylates in palladium-catalysed coupling reactions. Application to the synthesis of arylcoumarin inhibitors of gyrase B

  摘要：

  The palladium-catalysed coupling reaction between tosylate derivatives and organostannanes has been investigated as a methodology for carbon-carbon bond formation. Aryl substituents have been successfully incorporated even in highly functionalised coumarin structures to afford new analogues of the antibiotic novobiocin. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02351-5

文献信息

• Fine Tuning of physico-chemical parameters to optimise a new series of novobiocin analogues
  作者：Laurent Schio、Fabienne Chatreaux、Véronique Loyau、Michel Murer、Anne Ferreira、Pascale Mauvais、Alain Bonnefoy、Michel Klich

  DOI：10.1016/s0960-894x(01)00257-8

  日期：2001.6

  A novel series of novobiocin analogues has been synthesised by removing the lipophilic aryl chain in novobiocin and introducing an amino substituent. The structural modifications have been dictated by the control of lipophilicity and the dissociation constant of the resulting compounds. Antibacterial activity of the new coumarin derivatives could be correlated with the amount of uncharged form in physiological conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Tosylates in palladium-catalysed coupling reactions. Application to the synthesis of arylcoumarin inhibitors of gyrase B
  作者：Laurent Schio、Fabienne Chatreaux、Michel Klich

  DOI：10.1016/s0040-4039(99)02351-5

  日期：2000.3

  The palladium-catalysed coupling reaction between tosylate derivatives and organostannanes has been investigated as a methodology for carbon-carbon bond formation. Aryl substituents have been successfully incorporated even in highly functionalised coumarin structures to afford new analogues of the antibiotic novobiocin. (C) 2000 Elsevier Science Ltd. All rights reserved.