(1'R,3S)-3-(1'-hydroxy-3'-methylbutyl)-8-(benzyloxy)isochroman-1-one | 244203-42-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (1'R,3S)-3-(1'-hydroxy-3'-methylbutyl)-8-(benzyloxy)isochroman-1-one
• 英文别名: (3S)-3-[(1R)-1-hydroxy-3-methylbutyl]-8-phenylmethoxy-3,4-dihydroisochromen-1-one
• CAS: 244203-42-7
• 化学式: C₂₁H₂₄O₄
• 分子量: 340.419
• InChiKey: KVDUNWICCBJVKV-MJGOQNOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1'R,3S)-3-(1'-hydroxy-3'-methylbutyl)-8-(benzyloxy)isochroman-1-one 在 palladium dihydroxide 盐酸 、 sodium azide 、 18-冠醚-6 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 27.08h， 生成 (1S,3'S)-<1-(3,4-Dihydro-8-hydroxy-1-oxo-1H-2-benzopyran-3-yl)-3-methylbutyl> ammonium chloride
  参考文献：
  名称：

  A New Enantioselective Total Synthesis of AI-77-B

  摘要：

  [GRAPHICS]An enantioselective total synthesis of Al-77-B (1), a gastroprotective substance isolated from a culture broth of Bacillus pumilus Al- 77, was performed in high overall yield. In this synthesis, the dihydroisocoumarin part 14 and the dihydroxyamino acid part 20 were both assembled from D-ribose as the common chiral source, For the construction of 14 a bromobenzofuran derivative was used as a novel salicylic acid synthon. Finally, DEPC-mediated condensation of 14 and 20 yielded Al-77-B (1).

  DOI：

  10.1021/ol990102y
• 作为产物：
  描述：

  间溴苯酚 在 sodium hydrogensulfite sodium chlorite 、 sodium dihydrogenphosphate 、 高氯酸 、 双氧水 、 potassium carbonate 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 26.75h， 生成 (1'R,3S)-3-(1'-hydroxy-3'-methylbutyl)-8-(benzyloxy)isochroman-1-one
  参考文献：
  名称：

  A New Enantioselective Total Synthesis of AI-77-B

  摘要：

  [GRAPHICS]An enantioselective total synthesis of Al-77-B (1), a gastroprotective substance isolated from a culture broth of Bacillus pumilus Al- 77, was performed in high overall yield. In this synthesis, the dihydroisocoumarin part 14 and the dihydroxyamino acid part 20 were both assembled from D-ribose as the common chiral source, For the construction of 14 a bromobenzofuran derivative was used as a novel salicylic acid synthon. Finally, DEPC-mediated condensation of 14 and 20 yielded Al-77-B (1).

  DOI：

  10.1021/ol990102y