4-isopropyl-2-oxo-2H-chromen-7-yl p-toluenesulfonate | 1095851-18-5

• 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: 4-isopropyl-2-oxo-2H-chromen-7-yl p-toluenesulfonate
• 英文别名: (2-Oxo-4-propan-2-ylchromen-7-yl) 4-methylbenzenesulfonate
• CAS: 1095851-18-5
• 化学式: C₁₉H₁₈O₅S
• 分子量: 358.415
• InChiKey: CUEZWFUTWSRVIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-isopropyl-2-oxo-2H-chromen-7-yl p-toluenesulfonate 在 ruthenium trichloride 、 sodium periodate 、 cerium(III) chloride heptahydrate 作用下， 以 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 4.0h， 以95%的产率得到(+/-)-(3R,4R)-3,4-dihydroxy-4-propyl-2-oxo-2H-chromen-7-yl p-toluenesulfonate
  参考文献：
  名称：

  Dihydroxylation of Functionalized Coumarin Derivatives

  摘要：

  7-Acetoxy- and 7-tosyloxycoumarins were successfully dihydroxylated in RuCl3/NaIO4/CeCl3 system to give the corresponding glycol derivatives in excellent yields. Tricyclic coumarin with tetrasubstituted olefin function also gave the desired diol in good yield. Introduction of electron-deficient protecting group to coumarin skeleton is critical for the successful dihydroxylation.

  DOI：

  10.3987/com-08-s(f)29
• 作为产物：
  描述：

  7-羟基-4-异丙基-色烯-2-酮 、 对甲苯磺酰氯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以92%的产率得到4-isopropyl-2-oxo-2H-chromen-7-yl p-toluenesulfonate
  参考文献：
  名称：

  Dihydroxylation of Functionalized Coumarin Derivatives

  摘要：

  7-Acetoxy- and 7-tosyloxycoumarins were successfully dihydroxylated in RuCl3/NaIO4/CeCl3 system to give the corresponding glycol derivatives in excellent yields. Tricyclic coumarin with tetrasubstituted olefin function also gave the desired diol in good yield. Introduction of electron-deficient protecting group to coumarin skeleton is critical for the successful dihydroxylation.

  DOI：

  10.3987/com-08-s(f)29

文献信息

• Dihydroxylation of Functionalized Coumarin Derivatives
  作者：Takuya Kumamoto、Tsutomu Ishikawa、Keiko Fusegi、Waka Nakanishi

  DOI：10.3987/com-08-s(f)29

  日期：——

  7-Acetoxy- and 7-tosyloxycoumarins were successfully dihydroxylated in RuCl3/NaIO4/CeCl3 system to give the corresponding glycol derivatives in excellent yields. Tricyclic coumarin with tetrasubstituted olefin function also gave the desired diol in good yield. Introduction of electron-deficient protecting group to coumarin skeleton is critical for the successful dihydroxylation.