2-(3-bromo-5-formyl-6-hydroxy-4-methylphenyl)-1-butylthioacetic acid | 137644-96-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(3-bromo-5-formyl-6-hydroxy-4-methylphenyl)-1-butylthioacetic acid
• 英文别名: 2-(5-bromo-3-formyl-2-hydroxy-4-methylphenyl)-2-butylsulfanylacetic acid
• CAS: 137644-96-3
• 化学式: C₁₄H₁₇BrO₄S
• 分子量: 361.257
• InChiKey: XPMKRBNEUJHVSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  20.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  74.6
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(3-bromo-5-formyl-6-hydroxy-4-methylphenyl)-1-butylthioacetic acid 在 草酰氯 、 镍 作用下， 以 异丙醇 、 苯 为溶剂， 反应 18.0h， 生成 tert-butyl 3-(2,3-dihydro-6-methyl-2-oxobenzofuran-7-yl)propionate
  参考文献：
  名称：

  Pseudoguaianolides from intramolecular cycloadditions of aryl diazoketones: synthesis of (±)-confertin and an approach to the synthesis of (±)-damsin

  摘要：

  Rhodium(II) mandelate-catalysed cyclisation of alpha-diazoketones derived from 3-arylpropionic acids produces bicyclo[5.3.0]decatrienones, one of which has been used to synthesise an advanced (+/-)-confertin intermediate in six stages and 20% overall yield. The possibility of constructing intermediates for the synthesis of damsin-like pseudoguaianolides via catalysed diazoketone cyclisation is also examined and methods for the construction of polyfunctional 3-arylpropionic acids suitable for use as damsin precursors are presented.

  DOI：

  10.1039/p19910002565
• 作为产物：
  描述：

  3-溴-6-羟基-2-甲基苯甲醛 在 sodium hydroxide 、 四氯化锡 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 12.67h， 生成 2-(3-bromo-5-formyl-6-hydroxy-4-methylphenyl)-1-butylthioacetic acid
  参考文献：
  名称：

  Pseudoguaianolides from intramolecular cycloadditions of aryl diazoketones: synthesis of (±)-confertin and an approach to the synthesis of (±)-damsin

  摘要：

  Rhodium(II) mandelate-catalysed cyclisation of alpha-diazoketones derived from 3-arylpropionic acids produces bicyclo[5.3.0]decatrienones, one of which has been used to synthesise an advanced (+/-)-confertin intermediate in six stages and 20% overall yield. The possibility of constructing intermediates for the synthesis of damsin-like pseudoguaianolides via catalysed diazoketone cyclisation is also examined and methods for the construction of polyfunctional 3-arylpropionic acids suitable for use as damsin precursors are presented.

  DOI：

  10.1039/p19910002565