(1R,3R,16R)-3-hydroxy-4,11,18,18-tetramethyl-17-oxo-11-azapentacyclo[11.4.1.03,16.07,15.010,14]octadeca-4,7(15),8,10(14),12-pentaene-16-carbaldehyde | 1354631-32-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: (1R,3R,16R)-3-hydroxy-4,11,18,18-tetramethyl-17-oxo-11-azapentacyclo[11.4.1.03,16.07,15.010,14]octadeca-4,7(15),8,10(14),12-pentaene-16-carbaldehyde
• CAS: 1354631-32-5
• 化学式: C₂₂H₂₃NO₃
• 分子量: 349.43
• InChiKey: GJHUCQQBVMQMQW-JQOQJDEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  26.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• 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 以 甲苯 为溶剂， 反应 21.0h， 以65%的产率得到(1R,3R,16R)-3-hydroxy-4,11,18,18-tetramethyl-17-oxo-11-azapentacyclo[11.4.1.03,16.07,15.010,14]octadeca-4,7(15),8,10(14),12-pentaene-16-carbaldehyde
  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