(6,7-dimethoxy-1-methyl-1H-indol-3-yl)-acetic acid methyl ester | 908003-81-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (6,7-dimethoxy-1-methyl-1H-indol-3-yl)-acetic acid methyl ester
• 英文别名: methyl 2-(6,7-dimethoxy-1-methyl-1H-indol-3-yl)acetate；Methyl 2-(6,7-dimethoxy-1-methylindol-3-yl)acetate
• CAS: 908003-81-6
• 化学式: C₁₄H₁₇NO₄
• 分子量: 263.293
• InChiKey: VRMPEGIQTHZHRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  49.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (6,7-dimethoxy-1-methyl-1H-indol-3-yl)-acetic acid methyl ester 在 dirhodium tetraacetate 氢氧化钾 、 草酰氯 、 三氟化硼乙醚 、 magnesium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 、 苯 为溶剂， 反应 16.0h， 生成 [(1R,3S,4S,12R,16R)-7,8-dimethoxy-5-methyl-2,14,18-trioxo-17-oxa-5,15-diazahexacyclo[13.4.3.01,16.04,12.06,11.012,16]docosa-6(11),7,9-trien-3-yl] methyl carbonate
  参考文献：
  名称：

  Application of the Rh(II) Cyclization/Cycloaddition Cascade for the Total Synthesis of (±)-Aspidophytine

  摘要：

  A new strategy for the synthesis of (+/-)-aspidophytine has been developed and is based on a Rh(II)-catalyzed cyclization/dipolar cycloaddition sequence. The resulting [3+2]-cycloadduct undergoes an efficient Lewis acid mediated cascade that rapidly provides the complete skeleton of aspidophytine. The synthesis also features a mild decarbomethoxylation reaction.

  DOI：

  10.1021/ol061137i
• 作为产物：
  描述：

  4-溴-2-丁烯酸甲酯 在 palladium diacetate 、 四丁基碘化铵 、 三(邻甲基苯基)磷 氢氧化钾 、 碳酸氢钠 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 丙酮 、 乙腈 为溶剂， 反应 8.0h， 生成 (6,7-dimethoxy-1-methyl-1H-indol-3-yl)-acetic acid methyl ester
  参考文献：
  名称：

  Application of the Rh(II) Cyclization/Cycloaddition Cascade for the Total Synthesis of (±)-Aspidophytine

  摘要：

  A new strategy for the synthesis of (+/-)-aspidophytine has been developed and is based on a Rh(II)-catalyzed cyclization/dipolar cycloaddition sequence. The resulting [3+2]-cycloadduct undergoes an efficient Lewis acid mediated cascade that rapidly provides the complete skeleton of aspidophytine. The synthesis also features a mild decarbomethoxylation reaction.

  DOI：

  10.1021/ol061137i

文献信息

• Total Synthesis of the Alkaloid (±)-Aspidophytine Based on Carbonyl Ylide Cycloaddition Chemistry
  作者：José M. Mejía-Oneto、Albert Padwa

  DOI：10.1002/hlca.200890034

  日期：2008.2

  The RhII-catalyzed cycloaddition cascade of an indolyl-substituted α-diazo imide was used for the total synthesis of the complex pentacyclic alkaloid (±)-aspidophytine. Treatment of the resulting dipolar cycloadduct with BF3⋅OEt2 induces a domino fragmentation cascade. The reaction proceeds by an initial cleavage of the oxabicyclic ring and formation of a transient N-acyl iminium ion which reacts further

  上的Rh II催化的环加成级联的吲哚基-取代的α重氮酰亚胺被用于复杂的五环生物碱的全合成（±）-aspidophytine。用BF 3· OEt 2处理所得的偶极环加合物会诱发多米诺断裂级联反应。该反应通过最初的氧杂双环的裂解和形成瞬态的N-酰基亚胺基离子而进行，该N-酰基的亚胺基离子进一步与相邻的叔丁酯反应，并使所需的内酯环存在于蛇碱中。然后使用三步顺序除去酯基和OH基。随后的官能团操作可实现高产转化为（±）-aspidophytine。
• Application of the Rh(II) Cyclization/Cycloaddition Cascade for the Total Synthesis of (±)-Aspidophytine
  作者：José M. Mejía-Oneto、Albert Padwa

  DOI：10.1021/ol061137i

  日期：2006.7.1

  A new strategy for the synthesis of (+/-)-aspidophytine has been developed and is based on a Rh(II)-catalyzed cyclization/dipolar cycloaddition sequence. The resulting [3+2]-cycloadduct undergoes an efficient Lewis acid mediated cascade that rapidly provides the complete skeleton of aspidophytine. The synthesis also features a mild decarbomethoxylation reaction.