((2-thiazolylcarbonyl)methyl)triphenylphosphonium bromide | 136029-16-8

• 英文名称: ((2-thiazolylcarbonyl)methyl)triphenylphosphonium bromide
• 英文别名: [2-oxo-2-(1,3-thiazol-2-yl)ethyl]-triphenylphosphanium;bromide
• CAS: 136029-16-8
• 化学式: Br*C₂₃H₁₉NOPS
• 分子量: 468.354
• InChiKey: YSQUFPJNVFFOPC-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.32
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  29.96
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ((2-thiazolylcarbonyl)methyl)triphenylphosphonium bromide 在 氢氧化钾 作用下， 反应 0.5h， 生成 1-(thiazol-2-yl)-2-(triphenyl-λ⁵-phosphanylidene)ethan-1-one
  参考文献：
  名称：

  Stereoselective construction of polyhydroxyalkyl 2-thiazolyl ketones (thiazole ketoses) from d-glyceraldehyde and d-arabinose acetonides by wittig-michael sequence. a route to d-gluco-KDO

  摘要：

  The carbonylolefination of the title alkoxy aldehydes by 2-thiazolecarbonylmethylenetriphenyl-phosphorane 3 affords the corresponding (E)-enones which undergo syn-diastereoselective (ds, 85-95%) 1,4-conjugate addition of benzyl oxide anion; acid-catalyzed methanolysis of polyalkoxyalkyl ketones obtained in that way gives methyl 1-(2-thiazolyl)pyranoside precursors to ulosonic acids.

  DOI：

  10.1016/s0040-4039(00)79735-8
• 作为产物：
  描述：

  2-(溴乙酰基)-1,3-噻唑 、 三苯基膦 以 苯 为溶剂， 反应 24.0h， 生成 ((2-thiazolylcarbonyl)methyl)triphenylphosphonium bromide
  参考文献：
  名称：

  Stereoselective construction of polyhydroxyalkyl 2-thiazolyl ketones (thiazole ketoses) from d-glyceraldehyde and d-arabinose acetonides by wittig-michael sequence. a route to d-gluco-KDO

  摘要：

  The carbonylolefination of the title alkoxy aldehydes by 2-thiazolecarbonylmethylenetriphenyl-phosphorane 3 affords the corresponding (E)-enones which undergo syn-diastereoselective (ds, 85-95%) 1,4-conjugate addition of benzyl oxide anion; acid-catalyzed methanolysis of polyalkoxyalkyl ketones obtained in that way gives methyl 1-(2-thiazolyl)pyranoside precursors to ulosonic acids.

  DOI：

  10.1016/s0040-4039(00)79735-8

文献信息

• Dondoni, Alessandro; Marra, Alberto; Merino, Pedro, Journal of the American Chemical Society, 1994, vol. 116, # 8, p. 3324 - 3336
  作者：Dondoni, Alessandro、Marra, Alberto、Merino, Pedro

  DOI：——

  日期：——