(S)-6-hydroxy-6-(2-((S)-5-isopropyl-2-oxo-3-((R)-1-phenylethyl)imidazolidin-1-yl)-2-oxoethyl)indolo[2,1-b]quinazolin-12(6H)-one | 1447589-60-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: (S)-6-hydroxy-6-(2-((S)-5-isopropyl-2-oxo-3-((R)-1-phenylethyl)imidazolidin-1-yl)-2-oxoethyl)indolo[2,1-b]quinazolin-12(6H)-one
• 英文别名: (6S)-6-hydroxy-6-[2-oxo-2-[(5S)-2-oxo-3-[(1R)-1-phenylethyl]-5-propan-2-ylimidazolidin-1-yl]ethyl]indolo[2,1-b]quinazolin-12-one
• CAS: 1447589-60-7
• 化学式: C₃₁H₃₀N₄O₄
• 分子量: 522.604
• InChiKey: HGMLQLYFILJEEP-JNIUOZEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  39
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  93.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-6-hydroxy-6-(2-((S)-5-isopropyl-2-oxo-3-((R)-1-phenylethyl)imidazolidin-1-yl)-2-oxoethyl)indolo[2,1-b]quinazolin-12(6H)-one 在 sodium tetrahydroborate 、 nickel(II) chloride hexahydrate 作用下， 以 甲醇 为溶剂， 反应 14.0h， 以72%的产率得到(+)-(S,S)-3-hydroxy-2H-pyrrolo[2,3-b]indolo[5,5a,6-b,a]quinazoline-9-(8H)-7'-dione
  参考文献：
  名称：

  Total Synthesis of a Pyrroloindoloquinazoline Alkaloid

  摘要：

  A highly concise stereoselective synthesis of a newly identified alkaloid with a pyrroloindoloquinazoline skeleton has been achieved. To this end, a chiral auxiliary mediated asymmetric acetate aldol reaction on tryptanthrin was explored and the resulting adduct was converted to the product by a novel one-pot reductive cyclization/transamidation using NiCl2 center dot 6H(2)O/NaBH4 in methanol.

  DOI：

  10.1021/ol401709t
• 作为产物：
  描述：

  靛红酸酐 在 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.0h， 生成 (S)-6-hydroxy-6-(2-((S)-5-isopropyl-2-oxo-3-((R)-1-phenylethyl)imidazolidin-1-yl)-2-oxoethyl)indolo[2,1-b]quinazolin-12(6H)-one
  参考文献：
  名称：

  Total Synthesis of a Pyrroloindoloquinazoline Alkaloid

  摘要：

  A highly concise stereoselective synthesis of a newly identified alkaloid with a pyrroloindoloquinazoline skeleton has been achieved. To this end, a chiral auxiliary mediated asymmetric acetate aldol reaction on tryptanthrin was explored and the resulting adduct was converted to the product by a novel one-pot reductive cyclization/transamidation using NiCl2 center dot 6H(2)O/NaBH4 in methanol.

  DOI：

  10.1021/ol401709t