9-(benzyloxy)-8-cyano-1-ethoxy-3-(ethoxycarbonyl)-7,8-dihydro-6H-cyclopentisoquinoline | 172268-84-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 9-(benzyloxy)-8-cyano-1-ethoxy-3-(ethoxycarbonyl)-7,8-dihydro-6H-cyclopentisoquinoline
• 英文别名: ethyl 8-cyano-1-ethoxy-9-phenylmethoxy-7,8-dihydro-6H-cyclopenta[g]isoquinoline-3-carboxylate
• CAS: 172268-84-7
• 化学式: C₂₅H₂₄N₂O₄
• 分子量: 416.477
• InChiKey: MQQMYOPVPGSWGR-UHFFFAOYSA-N

物化性质

• 沸点：
  630.5±55.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  9-(benzyloxy)-8-cyano-1-ethoxy-3-(ethoxycarbonyl)-7,8-dihydro-6H-cyclopentisoquinoline 在 phosphate buffer 、 air 、 碘 、 二异丁基氢化铝 、 对甲苯磺酸 、 sodium bromide 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 22.83h， 生成 9-hydroxy-3-(1',3'-pentadienyl)-2,6,7,8-tetrahydro-1H-cyclopentisoquinolin-1,8-dione
  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：

  Diethyl 6-ethoxy-4-[(3-oxocyclopentyl)methyl]pyridine-2,5-dicarboxylate 在 乙醇 、 potassium tert-butylate 、 四丁基碘化铵 、 sodium hydride 、 potassium carbonate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.17h， 生成 9-(benzyloxy)-8-cyano-1-ethoxy-3-(ethoxycarbonyl)-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