1-(5-chloro-1-methyl-1H-pyrrol-3-yl)-2,2-dimethylpropan-1-one | 1605347-56-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(5-chloro-1-methyl-1H-pyrrol-3-yl)-2,2-dimethylpropan-1-one
• 英文别名: 1-(5-Chloro-1-methylpyrrol-3-yl)-2,2-dimethylpropan-1-one；1-(5-chloro-1-methylpyrrol-3-yl)-2,2-dimethylpropan-1-one
• CAS: 1605347-56-5
• 化学式: C₁₀H₁₄ClNO
• 分子量: 199.68
• InChiKey: PVLZUKNLKDQJMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-(1-methyl-1H-pyrrol-3-yl)-2,2-dimethyl-1-propanone 在 N-氯代丁二酰亚胺 作用下， 以 氯仿 为溶剂， 反应 12.0h， 以10%的产率得到1-(5-chloro-1-methyl-1H-pyrrol-3-yl)-2,2-dimethylpropan-1-one
  参考文献：
  名称：

  Palau’chlor: A Practical and Reactive Chlorinating Reagent

  摘要：

  Unlike its other halogen atom siblings, the utility of chlorinated arenes and (hetero)arenes are twofold: they are useful in tuning electronic structure as well as acting as points for diversification via cross-coupling. Herein we report the invention of a new guanidine-based chlorinating reagent, CBMG or "Palau'chlor", inspired by a key chlorospirocyclization en route to pyrrole imidazole alkaloids. This direct, mild, operationally simple, and safe chlorinating method is compatible with a range of nitrogen-containing heterocycles as well as select classes of arenes, conjugated pi-systems, sulfonamides, and silyl enol ethers. Comparisons with other known chlorinating reagents revealed CBMG to be the premier reagent.

  DOI：

  10.1021/ja5031744

文献信息

• Palau’chlor: A Practical and Reactive Chlorinating Reagent
  作者：Rodrigo A. Rodriguez、Chung-Mao Pan、Yuki Yabe、Yu Kawamata、Martin D. Eastgate、Phil S. Baran

  DOI：10.1021/ja5031744

  日期：2014.5.14

  Unlike its other halogen atom siblings, the utility of chlorinated arenes and (hetero)arenes are twofold: they are useful in tuning electronic structure as well as acting as points for diversification via cross-coupling. Herein we report the invention of a new guanidine-based chlorinating reagent, CBMG or "Palau'chlor", inspired by a key chlorospirocyclization en route to pyrrole imidazole alkaloids. This direct, mild, operationally simple, and safe chlorinating method is compatible with a range of nitrogen-containing heterocycles as well as select classes of arenes, conjugated pi-systems, sulfonamides, and silyl enol ethers. Comparisons with other known chlorinating reagents revealed CBMG to be the premier reagent.