[5-(diphenylphosphino)-2-(morpholin-4-yl)-1,3-thiazol-4-yl]acetic acid | 544466-66-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: [5-(diphenylphosphino)-2-(morpholin-4-yl)-1,3-thiazol-4-yl]acetic acid
• 英文别名: 2-(5-diphenylphosphanyl-2-morpholin-4-yl-1,3-thiazol-4-yl)acetic acid
• CAS: 544466-66-2
• 化学式: C₂₁H₂₁N₂O₃PS
• 分子量: 412.449
• InChiKey: IDLIVPQXKMKRHH-UHFFFAOYSA-N

物化性质

• 沸点：
  595.7±60.0 °C(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.37
• 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：
  0.24
• 拓扑面积：
  62.66
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-脱氧-2-氨基-b-D-葡萄糖 、 [5-(diphenylphosphino)-2-(morpholin-4-yl)-1,3-thiazol-4-yl]acetic acid 在 碳酸氢钠 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以94%的产率得到2-deoxy-2-({[2-(morpholin-4-yl)-5-(diphenylphosphino)-1,3-thiazol-4-yl]acetyl}amino)-D-glucopyranose
  参考文献：
  名称：

  Palladium-catalyzed Suzuki cross-coupling of aryl halides with aryl boronic acids in the presence of glucosamine-based phosphines

  摘要：

  Carbohydrate-substituted phosphines are easily obtained in quite good yields by coupling of protected or non-protected D-glucosamine with the corresponding diphenylphosphino acid. These neutral ligands, in association with palladium acetate, are very active catalysts in the Suzuki cross-coupling reaction. The polyhydroxy phosphines are more active than the peracetylated phosphines. The process tolerates electron-rich as well as electron-poor substituents. Excellent turnovers, up to 97 000 are observed. (C) 2003 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(03)00636-3
• 作为产物：
  描述：

  ethyl (2-morpholin-4-yl-1,3-thiazol-4-yl)acetate 在 sodium hydroxide 、 三乙胺 作用下， 以 吡啶 、 乙醇 为溶剂， 反应 20.0h， 生成 [5-(diphenylphosphino)-2-(morpholin-4-yl)-1,3-thiazol-4-yl]acetic acid
  参考文献：
  名称：

  Palladium-catalyzed Suzuki cross-coupling of aryl halides with aryl boronic acids in the presence of glucosamine-based phosphines

  摘要：

  Carbohydrate-substituted phosphines are easily obtained in quite good yields by coupling of protected or non-protected D-glucosamine with the corresponding diphenylphosphino acid. These neutral ligands, in association with palladium acetate, are very active catalysts in the Suzuki cross-coupling reaction. The polyhydroxy phosphines are more active than the peracetylated phosphines. The process tolerates electron-rich as well as electron-poor substituents. Excellent turnovers, up to 97 000 are observed. (C) 2003 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(03)00636-3