| 1236784-49-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• CAS: 1236784-49-8
• 化学式: C₇H₁₃N₂O₂*Cl
• 分子量: 192.645
• InChiKey: KUOWHGBMSDMHND-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -3.01
• 重原子数：
  12.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  27.27
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  咪唑 、 氯甲基甲基醚 以 N,N-二甲基甲酰胺-d7 为溶剂， 反应 72.0h， 以80%的产率得到
  参考文献：
  名称：

  Total Synthesis of Depsilairdin

  摘要：

  The total synthesis of depsilairdin, a host-selective phytotoxin isolated from Leptosphaeria maculans (the causal agent of blackleg disease of oilseed Brassicas), has been achieved by N-terminal extension of a suitably protected derivative of the hitherto unknown amino acid (2S,3S,4R)-3,4-dihydroxy-3-methyl-proline (Dhmp) followed by esterification with lairdinol A. The latter esterification, complicated by the sterically hindered nature of the carboxyl group, was accomplished by a novel method involving reaction of the 1-hydroxybenzotriazole (HOBt) derived active ester with the bromomagnesium alkoxide of lairdinol A. Three depsilairdin analogues were also prepared by replacing the Dhmp residue with L-proline and cis- and trans-4-hydroxy-L-proline. Phytotoxicity assays showed that the analogues were nontoxic to both blackleg-susceptible (brown mustard) and -resistant (canola) plants, suggesting that the presence of the Dhmp residue in depsilairdin is important for its host-selective toxicity toward brown mustard.

  DOI：

  10.1021/jo1009239