9-(benzyloxy)-8-cyano-1-ethoxy-3-((tert-butyldimethylsilyloxy)methyl)-7,8-dihydro-6H-cyclopentisoquinoline | 172268-92-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吖庚因类
• 英文名称: 9-(benzyloxy)-8-cyano-1-ethoxy-3-((tert-butyldimethylsilyloxy)methyl)-7,8-dihydro-6H-cyclopentisoquinoline
• CAS: 172268-92-7
• 化学式: C₂₉H₃₆N₂O₃Si
• 分子量: 488.702
• InChiKey: GHDCSKFBBDDMHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.29
• 重原子数：
  35.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  64.37
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  9-(benzyloxy)-8-cyano-1-ethoxy-3-((tert-butyldimethylsilyloxy)methyl)-7,8-dihydro-6H-cyclopentisoquinoline 在 phosphate buffer 、 二异丁基氢化铝 作用下， 生成 9-(benzyloxy)-1-ethoxy-3-((tert-butyldimethylsilyloxy)methyl)-7,8-dihydro-6H-cyclopentisoquinoline-8-carboxaldehyde
  参考文献：
  名称：

  Total Synthesis of Natural and ent-Fredericamycin A

  摘要：

  A total synthesis of both enantiomers of the potent antitumor-antibiotic fredericamycin A (1) is detailed based on a room temperature inverse electron demand Diels-Alder reaction of a N-sulfonyl-1-aza-1,3-butadiene for assemblage of a pyridone F ring precursor, a single-step Michael addition-intramolecular acylation for annulation of the DE ring system onto this pyridone F ring precursor, implementation of a regiospecific chromium carbene benzannulation reaction for AB ring construction, and a simple aldol closure for introduction of the spiro CD ring system. Resolution of the penultimate precursor 41 followed by deprotection provided natural and ent-fredericamycin A. The indistinguishable cytotoxic potency of the two enantiomers (L1210 IC50, 0.03 and 0.04 mu g/mL, respectively) is disclosed along with that of the key partial structures 2 (IC50 = 2 mu g/mL) and 21 IC50 = 7 mu g/mL) constituting the fully functionalized ABCDE and DEF ring systems of the natural product.

  DOI：

  10.1021/ja00153a004
• 作为产物：
  描述：

  3,6-bis(ethoxycarbonyl)-2,2-diethoxy-4-methyl-1-(methylsulfonyl)-1,2,3,4-tetrahydropyridine 在 咪唑 、 乙醇 、 potassium tert-butylate 、 四丁基碘化铵 、 二异丁基氢化铝 、 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 56.92h， 生成 9-(benzyloxy)-8-cyano-1-ethoxy-3-((tert-butyldimethylsilyloxy)methyl)-7,8-dihydro-6H-cyclopentisoquinoline
  参考文献：
  名称：

  Total Synthesis of Natural and ent-Fredericamycin A

  摘要：

  A total synthesis of both enantiomers of the potent antitumor-antibiotic fredericamycin A (1) is detailed based on a room temperature inverse electron demand Diels-Alder reaction of a N-sulfonyl-1-aza-1,3-butadiene for assemblage of a pyridone F ring precursor, a single-step Michael addition-intramolecular acylation for annulation of the DE ring system onto this pyridone F ring precursor, implementation of a regiospecific chromium carbene benzannulation reaction for AB ring construction, and a simple aldol closure for introduction of the spiro CD ring system. Resolution of the penultimate precursor 41 followed by deprotection provided natural and ent-fredericamycin A. The indistinguishable cytotoxic potency of the two enantiomers (L1210 IC50, 0.03 and 0.04 mu g/mL, respectively) is disclosed along with that of the key partial structures 2 (IC50 = 2 mu g/mL) and 21 IC50 = 7 mu g/mL) constituting the fully functionalized ABCDE and DEF ring systems of the natural product.

  DOI：

  10.1021/ja00153a004