methyl 5-[(1R,2R)-1,2-dihydroxypropyl]pyridine-2-carboxylate | 1154410-68-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: methyl 5-[(1R,2R)-1,2-dihydroxypropyl]pyridine-2-carboxylate
• CAS: 1154410-68-0
• 化学式: C₁₀H₁₃NO₄
• 分子量: 211.218
• InChiKey: XZXCYBBAXJQLFQ-MUWHJKNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  79.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (E)-methyl 5-(prop-1-en-1-yl)picolinate 在 乙酰胺 、 asymmetric dihydroxylation-mix-β 作用下， 以 水 、 叔丁醇 为溶剂， 反应 6.0h， 以100%的产率得到methyl 5-[(1R,2R)-1,2-dihydroxypropyl]pyridine-2-carboxylate
  参考文献：
  名称：

  First asymmetric synthesis of CJ-14877 and its enantiomer and their interleukin-1β inhibitory activities

  摘要：

  A potent antiinflammatory methyl picolinate alkaloid CJ-14877 [(+)-1] and its enantiomer (-)-1 were synthesized in two steps starting from commercially available methyl 5-bromopicolinate. The synthesis includes microwave-assisted Suzuki coupling reaction and Sharpless asymmetric dihydroxylation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.064

文献信息

• First asymmetric synthesis of CJ-14877 and its enantiomer and their interleukin-1β inhibitory activities
  作者：Yutaka Aoyagi、Yoshiyuki Adachi、Shunta Akagi、Naohito Ohno、Koichi Takeya

  DOI：10.1016/j.bmcl.2009.02.064

  日期：2009.4

  A potent antiinflammatory methyl picolinate alkaloid CJ-14877 [(+)-1] and its enantiomer (-)-1 were synthesized in two steps starting from commercially available methyl 5-bromopicolinate. The synthesis includes microwave-assisted Suzuki coupling reaction and Sharpless asymmetric dihydroxylation. (C) 2009 Elsevier Ltd. All rights reserved.