3-azido-2-(1-(benzyloxy)but-3-en-2-yl)-4,6-dimethoxy-5-methylphenyl acetate | 1441229-28-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3-azido-2-(1-(benzyloxy)but-3-en-2-yl)-4,6-dimethoxy-5-methylphenyl acetate
• 英文别名: [5-Azido-2,4-dimethoxy-3-methyl-6-(1-phenylmethoxybut-3-en-2-yl)phenyl] acetate；[5-azido-2,4-dimethoxy-3-methyl-6-(1-phenylmethoxybut-3-en-2-yl)phenyl] acetate
• CAS: 1441229-28-2
• 化学式: C₂₂H₂₅N₃O₅
• 分子量: 411.458
• InChiKey: JBAMCNNJVAIZGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  68.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-azido-2-(1-(benzyloxy)but-3-en-2-yl)-4,6-dimethoxy-5-methylphenyl acetate 在 (1S)-(+)-10-camphorsulfonic acid 、 三乙基硼 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 8.0h， 生成 9-((benzyloxy)methyl)-5,7-dimethoxy-6-methyl-3-oxo-2,3,9,9a-tetrahydro-1H-pyrrolo[1,2-a]indol-8-yl acetate
  参考文献：
  名称：

  Synthesis of a Leucomitosane via a Diastereoselective Radical Cascade

  摘要：

  The preparation of trans-2,3-disubstituted indolines from 1-azido-2-allylbenzene derivatives via a diastereoselective radical cascade using ethyl iodoacetate and triethylborane is described. Further lactamization afforded substituted benzopyrrolizidinones with excellent diastereomeric ratios. The radical cascade/lactamization sequence was efficiently applied to the synthesis of a 3-oxo-leucomitosane related to the mitomycin family of alkaloids.

  DOI：

  10.1021/jo4009904
• 作为产物：
  描述：

  2,4-二甲氧基-3-甲基苯酚 在 吡啶 、 盐酸 、 亚硝酸特丁酯 、 叠氮基三甲基硅烷 、 mercury(II) diacetate 、 硝酸 、 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙酸酐 、 溶剂黄146 、 丙酮 、 乙腈 、 mineral oil 为溶剂， 反应 40.42h， 生成 3-azido-2-(1-(benzyloxy)but-3-en-2-yl)-4,6-dimethoxy-5-methylphenyl acetate
  参考文献：
  名称：

  Synthesis of a Leucomitosane via a Diastereoselective Radical Cascade

  摘要：

  The preparation of trans-2,3-disubstituted indolines from 1-azido-2-allylbenzene derivatives via a diastereoselective radical cascade using ethyl iodoacetate and triethylborane is described. Further lactamization afforded substituted benzopyrrolizidinones with excellent diastereomeric ratios. The radical cascade/lactamization sequence was efficiently applied to the synthesis of a 3-oxo-leucomitosane related to the mitomycin family of alkaloids.

  DOI：

  10.1021/jo4009904

文献信息

• Synthesis of a Leucomitosane via a Diastereoselective Radical Cascade
  作者：François Brucelle、Philippe Renaud

  DOI：10.1021/jo4009904

  日期：2013.6.21

  The preparation of trans-2,3-disubstituted indolines from 1-azido-2-allylbenzene derivatives via a diastereoselective radical cascade using ethyl iodoacetate and triethylborane is described. Further lactamization afforded substituted benzopyrrolizidinones with excellent diastereomeric ratios. The radical cascade/lactamization sequence was efficiently applied to the synthesis of a 3-oxo-leucomitosane related to the mitomycin family of alkaloids.