| 1354631-34-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• CAS: 1354631-34-7
• 化学式: C₂₂H₂₅NO₃
• 分子量: 351.445
• InChiKey: IAEVPLMZXPUVSC-CUJSYCCXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.05
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  59.3
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  在 溶剂黄146 、 肼 作用下， 以 乙醇 为溶剂， 反应 13.0h， 生成
  参考文献：
  名称：

  A Unified Route to the Welwitindolinone Alkaloids: Total Syntheses of (−)-N-Methylwelwitindolinone C Isothiocyanate, (−)-N-Methylwelwitindolinone C Isonitrile, and (−)-3-Hydroxy-N-methylwelwitindolinone C Isothiocyanate

  摘要：

  As part of a comprehensive strategy to the welwitindolinone alkaloids possessing a bicyclo[4.3.1]decane core, we report herein concise asymmetric total syntheses of (-)-N-methylwelwitindolinone C isothiocyanate (2a), (-)-N-methylwelwitindolinone C isonitrile (2b), and (-)-3-hydroxy-N-methylwelwitindolinone C isothiocyanate (3a) from a common tetracyclic intermediate. The crucial vinyl chloride moiety was installed through electrophilic chlorination of a hydrazone, but only after adjustment of reactivity to circumvent a facile skeletal rearrangement. Selective desulfurization and oxidation of 2a provided access to 2b and 3a, respectively. Notably, this work provides corrected H-1 and C-13 NMR spectral data for 3a.

  DOI：

  10.1021/ja210793x
• 作为产物：
  描述：

  3-ethenyl-3,7,7,10-tetramethyl-4,16-dioxo-10-azatetracyclo[6.6.1.1^2,6.0^11,15]-hexadeca-1(14),8,11(15),12-tetraene-2-carbaldehyde 在 甲醇 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 0.25h， 以89%的产率得到
  参考文献：
  名称：

  A Unified Route to the Welwitindolinone Alkaloids: Total Syntheses of (−)-N-Methylwelwitindolinone C Isothiocyanate, (−)-N-Methylwelwitindolinone C Isonitrile, and (−)-3-Hydroxy-N-methylwelwitindolinone C Isothiocyanate

  摘要：

  As part of a comprehensive strategy to the welwitindolinone alkaloids possessing a bicyclo[4.3.1]decane core, we report herein concise asymmetric total syntheses of (-)-N-methylwelwitindolinone C isothiocyanate (2a), (-)-N-methylwelwitindolinone C isonitrile (2b), and (-)-3-hydroxy-N-methylwelwitindolinone C isothiocyanate (3a) from a common tetracyclic intermediate. The crucial vinyl chloride moiety was installed through electrophilic chlorination of a hydrazone, but only after adjustment of reactivity to circumvent a facile skeletal rearrangement. Selective desulfurization and oxidation of 2a provided access to 2b and 3a, respectively. Notably, this work provides corrected H-1 and C-13 NMR spectral data for 3a.

  DOI：

  10.1021/ja210793x