N-cyclopropyl-2,3-dihydro-1,4-benzodioxine-6-carboxamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: N-cyclopropyl-2,3-dihydro-1,4-benzodioxine-6-carboxamide
• 化学式: C₁₂H₁₃NO₃
• mdl: MFCD08724820
• 分子量: 219.24
• InChiKey: WMFVOPOLLRHCBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙醇 、 N-cyclopropyl-2,3-dihydro-1,4-benzodioxine-6-carboxamide 在 (4-cyanopyridine)bis(dimethylglyoximato)cobalt(III) chloride 、 Ir[dF(CF₃)ppy]₂(5,5'-dCF₃bpy)PF₆ 作用下， 以 二氯甲烷 为溶剂， 以67 %的产率得到N-(1-ethoxyallyl)-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxamide
  参考文献：
  名称：

  Cooperative Photoredox and Cobalt‐catalyzed Acceptorless Dehydrogenative Functionalization of Cyclopropylamides towards Allylic N,O‐Acyl‐acetal Derivatives

  摘要：

  We disclose herein a novel photoredox and cobalt co‐catalyzed ring‐opening/acceptorless dehydrogenative functionalization of mono‐donor cyclopropanes, which providing a sustainable and atom‐economic approach to rapidly assemble a wide range of allylic N,O‐acyl‐acetal derivatives. The optimized conditions accommodate assorted cycloalkylamides and primary, secondary and tertiary alcohols, with applications in late‐stage functionalization of pharmaceutically relevant compounds, stimulating the further utility in medicinal chemistry. Moreover, selective nucleophilic substitutions with various carbon nucleophiles were succeed in a one‐pot fashion, offering a reliable avenue to access some cyclic and acyclic derivatives.

  DOI：

  10.1002/anie.202401579
• 作为产物：
  描述：

  环丙胺 、 2,3-二氢-1,4-苯并二噁烷-6-羧酸 在 N,N'-羰基二咪唑 作用下， 以 二氯甲烷 为溶剂， 以95 %的产率得到N-cyclopropyl-2,3-dihydro-1,4-benzodioxine-6-carboxamide
  参考文献：
  名称：

  Cooperative Photoredox and Cobalt‐catalyzed Acceptorless Dehydrogenative Functionalization of Cyclopropylamides towards Allylic N,O‐Acyl‐acetal Derivatives

  摘要：

  We disclose herein a novel photoredox and cobalt co‐catalyzed ring‐opening/acceptorless dehydrogenative functionalization of mono‐donor cyclopropanes, which providing a sustainable and atom‐economic approach to rapidly assemble a wide range of allylic N,O‐acyl‐acetal derivatives. The optimized conditions accommodate assorted cycloalkylamides and primary, secondary and tertiary alcohols, with applications in late‐stage functionalization of pharmaceutically relevant compounds, stimulating the further utility in medicinal chemistry. Moreover, selective nucleophilic substitutions with various carbon nucleophiles were succeed in a one‐pot fashion, offering a reliable avenue to access some cyclic and acyclic derivatives.

  DOI：

  10.1002/anie.202401579

文献信息

• Cooperative Photoredox and Cobalt‐catalyzed Acceptorless Dehydrogenative Functionalization of Cyclopropylamides towards Allylic N,O‐Acyl‐acetal Derivatives
  作者：Haohao Huang、Xinjun Luan、Zhijun Zuo

  DOI：10.1002/anie.202401579

  日期：——

  We disclose herein a novel photoredox and cobalt co‐catalyzed ring‐opening/acceptorless dehydrogenative functionalization of mono‐donor cyclopropanes, which providing a sustainable and atom‐economic approach to rapidly assemble a wide range of allylic N,O‐acyl‐acetal derivatives. The optimized conditions accommodate assorted cycloalkylamides and primary, secondary and tertiary alcohols, with applications in late‐stage functionalization of pharmaceutically relevant compounds, stimulating the further utility in medicinal chemistry. Moreover, selective nucleophilic substitutions with various carbon nucleophiles were succeed in a one‐pot fashion, offering a reliable avenue to access some cyclic and acyclic derivatives.