sarcodonin ε | 1430111-14-0

• 分子结构分类: 有机化合物
• 英文名称: sarcodonin ε
• CAS: 1430111-14-0
• 化学式: C₃₉H₄₂N₂O₁₅
• 分子量: 778.767
• InChiKey: NRVZSPZDTGDADG-RKFXEXHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.04
• 重原子数：
  56.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  216.72
• 氢给体数：
  2.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  sarcodonin ε 、 乙酸酐 在 吡啶 作用下， 反应 2.0h， 以18 mg的产率得到
  参考文献：
  名称：

  Establishment of Benzodioxazine Core Structure for Sarcodonin Class of Natural Products by X-ray Analysis

  摘要：

  Sarcodonin epsilon (2), isolated from Sarcodon scabrosus, was treated with trimethylsilyldiazomethane to yield a crystalline methylated derivative 6. The structure of 6 was determined by X-ray analysis, which confirmed the presence of an unprecedented N(1b)-OMe group, the configuration at N(1b) and the 1,3,4-substituted phenyl ring structure of 2. More importantly, the structures of 6 and 2 have answered the intriguing problem of solving the core structure of the sarcodonin class of natural products, establishing that sarcodonins have a benzodioxazine core structure, rather than the recently proposed benzodioxane aminal core structure.

  DOI：

  10.1021/ol400595k
• 作为产物：
  描述：

  在 5% palladium on barium sulphate 、 氢气 作用下， 以 甲醇 为溶剂， 23.0 ℃ 、101.33 kPa 条件下， 反应 0.5h， 生成 sarcodonin ε 、 epi-sarcodonin ε
  参考文献：
  名称：

  Convergent Synthesis and Structural Confirmation of Phellodonin and Sarcodonin ε

  摘要：

  The first synthesis of members of the sarcodonin family, phellodonin and sarcodonin epsilon, is reported herein. This verifies that the unprecedented and seemingly unstable N,N-dioxide-containing benzodioxazine framework can be constructed in the laboratory and lends further support to the proposed structures. The key step in the synthesis involves a biomimetic hetero-Diels-Alder reaction between a pyrazine N-oxide and an ortho-quinone.

  DOI：

  10.1021/ol400709f