methyl 2-[(Z)-1-carbomethoxy-5-fluoro-2-hydroxy-1,2-dihydro-3H-indol-3-ylidene]-2-cyanoacetate | 575446-63-8

• 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: methyl 2-[(Z)-1-carbomethoxy-5-fluoro-2-hydroxy-1,2-dihydro-3H-indol-3-ylidene]-2-cyanoacetate
• 英文别名: methyl (3Z)-3-(1-cyano-2-methoxy-2-oxoethylidene)-5-fluoro-2-hydroxy-2H-indole-1-carboxylate
• CAS: 575446-63-8
• 化学式: C₁₄H₁₁FN₂O₅
• 分子量: 306.25
• InChiKey: CJJGNAZHHGHVCT-LUAWRHEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  99.9
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  溴乙烷 、 methyl 2-[(Z)-1-carbomethoxy-5-fluoro-2-hydroxy-1,2-dihydro-3H-indol-3-ylidene]-2-cyanoacetate 在 magnesium 作用下， 以 乙醚 、 四氢呋喃 为溶剂， 反应 3.5h， 生成 methyl 3exo-cyano-3a-ethyl-5-fluoro-2-oxo-2,3,3a,8a-tetrahydro-8H-furo[2,3-b]indole-8-carboxylate 、 methyl 3endo-cyano-3a-ethyl-5-fluoro-2-oxo-2,3,3a,8a-tetrahydro-8H-furo[2,3-b]indole-8-carboxylate
  参考文献：
  名称：

  A convenient preparation of furo[2,3-b]indoles by conjugated addition of organomagnesium reagents to 2-hydroxyindolylidenemalonates

  摘要：

  The chelate-controlled conjugated addition of Grignard reagents to 2-hydroxyindolylidenemalonates was studied as a means of preparing 3a-alkyl-3-methoxycarbonyl-2-oxofuro[2,3-b]indoles in one or two steps. In addition to the alkylorganometallic group variation, the effects of substitution at the aromatic ring on the reaction outcome were established. The indolylidenemalonates were found to be less reactive than the analogous indolylidenecyanoacetates. (C) 2003 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(03)00336-3
• 作为产物：
  描述：

  methyl 2-(1-carbomethoxy-5-fluoro-1H-indol-3-yl)-2-cyanoacetate 在 chromium(VI) oxide 作用下， 以 溶剂黄146 为溶剂， 以67%的产率得到methyl 2-[(Z)-1-carbomethoxy-5-fluoro-2-hydroxy-1,2-dihydro-3H-indol-3-ylidene]-2-cyanoacetate
  参考文献：
  名称：

  A convenient preparation of furo[2,3-b]indoles by conjugated addition of organomagnesium reagents to 2-hydroxyindolylidenemalonates

  摘要：

  The chelate-controlled conjugated addition of Grignard reagents to 2-hydroxyindolylidenemalonates was studied as a means of preparing 3a-alkyl-3-methoxycarbonyl-2-oxofuro[2,3-b]indoles in one or two steps. In addition to the alkylorganometallic group variation, the effects of substitution at the aromatic ring on the reaction outcome were established. The indolylidenemalonates were found to be less reactive than the analogous indolylidenecyanoacetates. (C) 2003 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(03)00336-3