3-(6-hydroxybenzo[d][1,3]dioxol-5-yl)-3-(4-methoxyphenyl)-1-(1H-pyrrol-1-yl)propan-1-one | 1064065-78-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 3-(6-hydroxybenzo[d][1,3]dioxol-5-yl)-3-(4-methoxyphenyl)-1-(1H-pyrrol-1-yl)propan-1-one
• 英文别名: 3-(6-Hydroxy-1,3-benzodioxol-5-yl)-3-(4-methoxyphenyl)-1-pyrrol-1-ylpropan-1-one
• CAS: 1064065-78-6
• 化学式: C₂₁H₁₉NO₅
• 分子量: 365.386
• InChiKey: MKQHKPIXZUYMAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  69.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(6-hydroxybenzo[d][1,3]dioxol-5-yl)-3-(4-methoxyphenyl)-1-(1H-pyrrol-1-yl)propan-1-one 在 borane tetrahydrofuran 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 trans-1-(8-(4-methoxyphenyl)-7,8-dihydro-6H-[1,3]dioxolo[4,5-g]chromen-6-yl)-1H-pyrrole 、 cis-1-(8-(4-methoxyphenyl)-7,8-dihydro-6H-[1,3]dioxolo[4,5-g]chromen-6-yl)-1H-pyrrole
  参考文献：
  名称：

  Reduction of Pyrrolyl- and Indolylamides with BH₃·THF: Cyclodeoxygenation versus Deoxygenation

  摘要：

  Herein we report that borane reductions of acylpyrroles and acylindoles that contain a pendant phenol take two different paths. Acylpyrroles undergo a reductive cyclization to make unusual chromanyl pyrroles. Treatment of related acylindoles under identical conditions results in deoxygenation without cyclization. The results are interpreted in terms of relative rates of cyclization and reduction of intermediate carbenium ions, where cyclization of the indole-stablized carbenium ion is slower.

  DOI：

  10.1021/jo801627z
• 作为产物：
  描述：

  吡咯 、 8-(4-methoxyphenyl)-7,8-dihydro-6H-[1,3]dioxolo[4,5-g]-chromen-6-one 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 以56%的产率得到3-(6-hydroxybenzo[d][1,3]dioxol-5-yl)-3-(4-methoxyphenyl)-1-(1H-pyrrol-1-yl)propan-1-one
  参考文献：
  名称：

  Reduction of Pyrrolyl- and Indolylamides with BH₃·THF: Cyclodeoxygenation versus Deoxygenation

  摘要：

  Herein we report that borane reductions of acylpyrroles and acylindoles that contain a pendant phenol take two different paths. Acylpyrroles undergo a reductive cyclization to make unusual chromanyl pyrroles. Treatment of related acylindoles under identical conditions results in deoxygenation without cyclization. The results are interpreted in terms of relative rates of cyclization and reduction of intermediate carbenium ions, where cyclization of the indole-stablized carbenium ion is slower.

  DOI：

  10.1021/jo801627z

文献信息

• Reduction of Pyrrolyl- and Indolylamides with BH₃·THF: Cyclodeoxygenation versus Deoxygenation
  作者：Kelin Li、Jon A. Tunge

  DOI：10.1021/jo801627z

  日期：2008.11.7

  Herein we report that borane reductions of acylpyrroles and acylindoles that contain a pendant phenol take two different paths. Acylpyrroles undergo a reductive cyclization to make unusual chromanyl pyrroles. Treatment of related acylindoles under identical conditions results in deoxygenation without cyclization. The results are interpreted in terms of relative rates of cyclization and reduction of intermediate carbenium ions, where cyclization of the indole-stablized carbenium ion is slower.