1-(5-Bromo-2-hydroxy-4-methoxyphenyl)propan-1-one | 1114598-42-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(5-Bromo-2-hydroxy-4-methoxyphenyl)propan-1-one
• CAS: 1114598-42-3
• 化学式: C₁₀H₁₁BrO₃
• mdl: MFCD11983428
• 分子量: 259.1
• InChiKey: LABHOHBLMGKXRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(5-Bromo-2-hydroxy-4-methoxyphenyl)propan-1-one 、 3-溴-4,6-二硝基氟苯 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 生成
  参考文献：
  名称：

  An Efficient Process for the Large-Scale Synthesis of a 2,3,6-Trisubstituted Indole

  摘要：

  The efficient synthesis of a key trisubstituted indole intermediate 1 is described. The synthetic route required the use of an aryl Grignard reagent which was not commercially available, and the large-scale formation of this fragment and the thermal evaluation for this step is presented. The key step in the sequence was a Truce-Smiles rearrangement to provide an advanced ketone intermediate which, upon reduction, cyclized to the desired indole 1. Design of experiment (DoE) optimization of this reduction is also presented. In total >50 kg of target indole 1 were synthesized in 55% overall yield over five steps using this new route.

  DOI：

  10.1021/op300303p

文献信息

• An Efficient Process for the Large-Scale Synthesis of a 2,3,6-Trisubstituted Indole
  作者：Anthony D. Alorati、Andrew D. Gibb、Peter R. Mullens、Gavin W. Stewart

  DOI：10.1021/op300303p

  日期：2012.12.21

  The efficient synthesis of a key trisubstituted indole intermediate 1 is described. The synthetic route required the use of an aryl Grignard reagent which was not commercially available, and the large-scale formation of this fragment and the thermal evaluation for this step is presented. The key step in the sequence was a Truce-Smiles rearrangement to provide an advanced ketone intermediate which, upon reduction, cyclized to the desired indole 1. Design of experiment (DoE) optimization of this reduction is also presented. In total >50 kg of target indole 1 were synthesized in 55% overall yield over five steps using this new route.