5,8-bis(methoxymethoxy)-9,9'-bis(phenylmethoxy)-6',7'-dihydro-4,6-dimethoxy-1'-ethoxy-3-hydroxy-3'-(1",3"-pentadienyl)spiro<2H-benzindene-2,8'-8'H-cyclopentisoquinolin>-1(3H)-one | 1026535-33-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 5,8-bis(methoxymethoxy)-9,9'-bis(phenylmethoxy)-6',7'-dihydro-4,6-dimethoxy-1'-ethoxy-3-hydroxy-3'-(1",3"-pentadienyl)spiro<2H-benzindene-2,8'-8'H-cyclopentisoquinolin>-1(3H)-one
• 英文别名: 5,8-bis(methoxymethoxy)-9,9'-bis(phenylmethoxy)-6',7'-dihydro-4,6-dimethoxy-1'-ethoxy-3-hydroxy-3'-(1",3"-pentadienyl)spiro[2H-benz[f]indene-2,8'-8'H-cyclopent[g]isoquinolin]-1(3H)-one；1'-ethoxy-3-hydroxy-4,6-dimethoxy-5,8-bis(methoxymethoxy)-3'-[(1E,3E)-penta-1,3-dienyl]-9,9'-bis(phenylmethoxy)spiro[3H-cyclopenta[b]naphthalene-2,8'-6,7-dihydrocyclopenta[g]isoquinoline]-1-one
• CAS: 1026535-33-0
• 化学式: C₅₁H₅₁NO₁₁
• 分子量: 853.966
• InChiKey: YNGXIRBLFKEPFU-QHWAJSKBSA-N

物化性质

• 沸点：
  988.6±65.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  63
• 可旋转键数：
  18
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  133
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  5,8-bis(methoxymethoxy)-9,9'-bis(phenylmethoxy)-6',7'-dihydro-4,6-dimethoxy-1'-ethoxy-3-hydroxy-3'-(1",3"-pentadienyl)spiro<2H-benzindene-2,8'-8'H-cyclopentisoquinolin>-1(3H)-one 在 air 、 三溴化硼 、 二甲基亚砜 、 三乙胺 、 三氟乙酸酐 作用下， 反应 5.5h， 生成
  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：

  在 咪唑 、 四丁基氟化铵 、 乙酸酐 、 四丁基碘化铵 、 potassium carbonate 、 二甲基亚砜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 正庚烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 153.5h， 生成 5,8-bis(methoxymethoxy)-9,9'-bis(phenylmethoxy)-6',7'-dihydro-4,6-dimethoxy-1'-ethoxy-3-hydroxy-3'-(1",3"-pentadienyl)spiro<2H-benzindene-2,8'-8'H-cyclopentisoquinolin>-1(3H)-one
  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