methyl 2-(toluene-4-sulfonyloxy)indole-3-carboxylate

• 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-(toluene-4-sulfonyloxy)indole-3-carboxylate
• 英文别名: 3-methoxycarbonyl-2-(p-toluenesulfoxy)indole；methyl 2-(4-methylphenyl)sulfonyloxy-1H-indole-3-carboxylate
• 化学式: C₁₇H₁₅NO₅S
• 分子量: 345.376
• InChiKey: XEUMUBOYCUDDJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  93.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-(toluene-4-sulfonyloxy)indole-3-carboxylate 、 ethyl (1S,5R)-2-oxo-3-oxabicyclo[3.1.0]hexane-1-carboxylate 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以68%的产率得到(3aR,10aS)-3a-ethyl 4-methyl 3-oxo-3a,10a-dihydro-1H,10H-furo[3,4-c]pyrrolo[1,2-a]indole-3a,4-dicarboxylate
  参考文献：
  名称：

  One-Step Synthesis of Heteroaromatic-Fused Pyrrolidines via Cyclopropane Ring-Opening Reaction:  Application to the PKCβ Inhibitor JTT-010

  摘要：

  A ring-opening reaction of cyclopropanes with five-membered heteroaromatics having a leaving group at C(2) was found to provide heteroaromatic-fused pyrrolidines in one step. This reaction was successfully applied to the synthesis of the protein kinase C-beta inhibitor JTT-010, which possesses a dihydropyrrolo[1,2-a]indole core.

  DOI：

  10.1021/ol071336h
• 作为产物：
  描述：

  苯甲醯亞胺酸 、 对甲苯磺酰氯 、 碳酸二甲酯 在 sodium hydride 作用下， 以 N,N-二甲基乙酰胺 、 xylene 为溶剂， 反应 20.0h， 以57%的产率得到methyl 2-(toluene-4-sulfonyloxy)indole-3-carboxylate
  参考文献：
  名称：

  One-Step Synthesis of Heteroaromatic-Fused Pyrrolidines via Cyclopropane Ring-Opening Reaction:  Application to the PKCβ Inhibitor JTT-010

  摘要：

  A ring-opening reaction of cyclopropanes with five-membered heteroaromatics having a leaving group at C(2) was found to provide heteroaromatic-fused pyrrolidines in one step. This reaction was successfully applied to the synthesis of the protein kinase C-beta inhibitor JTT-010, which possesses a dihydropyrrolo[1,2-a]indole core.

  DOI：

  10.1021/ol071336h

文献信息

• One-Step Synthesis of Heteroaromatic-Fused Pyrrolidines via Cyclopropane Ring-Opening Reaction:  Application to the PKCβ Inhibitor JTT-010
  作者：Masahiro Tanaka、Minoru Ubukata、Takafumi Matsuo、Katsutaka Yasue、Katsuya Matsumoto、Yasuyuki Kajimoto、Takashi Ogo、Takashi Inaba

  DOI：10.1021/ol071336h

  日期：2007.8.1

  A ring-opening reaction of cyclopropanes with five-membered heteroaromatics having a leaving group at C(2) was found to provide heteroaromatic-fused pyrrolidines in one step. This reaction was successfully applied to the synthesis of the protein kinase C-beta inhibitor JTT-010, which possesses a dihydropyrrolo[1,2-a]indole core.