[2-(4-Fluorophenyl)-3-(oxan-4-yl)oxiran-2-yl]methanol | 1394008-11-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: [2-(4-Fluorophenyl)-3-(oxan-4-yl)oxiran-2-yl]methanol
• CAS: 1394008-11-7
• 化学式: C₁₄H₁₇FO₃
• 分子量: 252.286
• InChiKey: YOXQOMSOJGFSAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [2-(4-Fluorophenyl)-3-(oxan-4-yl)oxiran-2-yl]methanol 在 sodium periodate 、 rhodium(III) chloride hydrate 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 反应 24.0h， 生成 (2R,3S)-2-(4-fluorophenyl)-3-(oxan-4-yl)oxirane-2-carboxylic acid 、 2-[(2S,3S)-2-(4-fluorobenzoyl)-5-oxooxolan-3-yl]acetic acid
  参考文献：
  名称：

  Investigation on the oxidation of aryl oxiranylmethanols and the synthesis of 2-aryl-N-thiazolyl-oxirane-2-carboxamides as glucokinase activators

  摘要：

  RuCl3/NaIO4-initiated oxidation of oxiranemethanols was investigated, and two products, oxirane-2-carboxylic acid and (5'-oxotetrahydrofuran-3-yl)acetic acid, were obtained in variant ratios. The product structures were determined and a tentative mechanism involving oxidation-rearrangement-oxidation process was proposed. Glucokinase enzymatic assay revealed that oxiranecarboxamides 4a-c retained moderate GK activation potency with amide 4a showing an EC50 value of 584 nM and a high activation fold of 3.14. However, (5'-oxotetrahydrofuran-3-yl)acetamide ha is inactive. This study not only provided an alternative protocol to access (5'-oxotetrahydrofuran-3-yl)acetic acid analogs, but also yielded nanomolar GA activators (esp. 4a) for further structure-activity relationship study. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.06.111
• 作为产物：
  描述：

  在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 [2-(4-Fluorophenyl)-3-(oxan-4-yl)oxiran-2-yl]methanol
  参考文献：
  名称：

  Investigation on the oxidation of aryl oxiranylmethanols and the synthesis of 2-aryl-N-thiazolyl-oxirane-2-carboxamides as glucokinase activators

  摘要：

  RuCl3/NaIO4-initiated oxidation of oxiranemethanols was investigated, and two products, oxirane-2-carboxylic acid and (5'-oxotetrahydrofuran-3-yl)acetic acid, were obtained in variant ratios. The product structures were determined and a tentative mechanism involving oxidation-rearrangement-oxidation process was proposed. Glucokinase enzymatic assay revealed that oxiranecarboxamides 4a-c retained moderate GK activation potency with amide 4a showing an EC50 value of 584 nM and a high activation fold of 3.14. However, (5'-oxotetrahydrofuran-3-yl)acetamide ha is inactive. This study not only provided an alternative protocol to access (5'-oxotetrahydrofuran-3-yl)acetic acid analogs, but also yielded nanomolar GA activators (esp. 4a) for further structure-activity relationship study. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.06.111