Ethyl 4-(2-bromo-4,6-difluorophenoxy)-3-oxobutanoate | 1393846-82-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: Ethyl 4-(2-bromo-4,6-difluorophenoxy)-3-oxobutanoate
• 英文别名: ethyl 4-(2-bromo-4,6-difluorophenoxy)-3-oxobutanoate
• CAS: 1393846-82-6
• 化学式: C₁₂H₁₁BrF₂O₄
• mdl: MFCD27816495
• 分子量: 337.118
• InChiKey: SRTMGPJKBSUUDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Ethyl 4-(2-bromo-4,6-difluorophenoxy)-3-oxobutanoate 在 copper(l) iodide 、 硫酸 、 potassium carbonate 、 N,N'-二甲基乙二胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 22.5h， 生成 6,8-difluorochroman-3-one
  参考文献：
  名称：

  Process Research for Multikilogram Production of Etamicastat: A Novel Dopamine β-Hydroxylase Inhibitor

  摘要：

  In order to develop a manufacturing route to etamicastat, three synthetic approaches to the pivotal chiral 3-aminochroman intermediate have been studied as well as four methods for the construction of the 2-aminoethyl imidazolethione fragment. The evolution of the synthetic strategy based on the early discovery route was described. By focusing on the use of readily available starting materials it was possible to avoid chromatography steps and expensive reagents, bringing about significant improvements in cost and throughput. The best route involves construction of the chiral centre by asymmetric hydrogenation.

  DOI：

  10.1021/op300012d
• 作为产物：
  描述：

  6,8-difluoro-2H-chromene-3-carbonitrile 在 sodium hypochlorite 、 硫酸 、 水 、 氢气 、 溴 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 溶剂黄146 、 二甲基亚砜 为溶剂， 100.0 ℃ 、3.0 MPa 条件下， 反应 72.5h， 生成 Ethyl 4-(2-bromo-4,6-difluorophenoxy)-3-oxobutanoate
  参考文献：
  名称：

  Process Research for Multikilogram Production of Etamicastat: A Novel Dopamine β-Hydroxylase Inhibitor

  摘要：

  In order to develop a manufacturing route to etamicastat, three synthetic approaches to the pivotal chiral 3-aminochroman intermediate have been studied as well as four methods for the construction of the 2-aminoethyl imidazolethione fragment. The evolution of the synthetic strategy based on the early discovery route was described. By focusing on the use of readily available starting materials it was possible to avoid chromatography steps and expensive reagents, bringing about significant improvements in cost and throughput. The best route involves construction of the chiral centre by asymmetric hydrogenation.

  DOI：

  10.1021/op300012d

文献信息

• Process Research for Multikilogram Production of Etamicastat: A Novel Dopamine β-Hydroxylase Inhibitor
  作者：Alexandre Beliaev、Jorge Wahnon、Domenico Russo

  DOI：10.1021/op300012d

  日期：2012.4.20

  In order to develop a manufacturing route to etamicastat, three synthetic approaches to the pivotal chiral 3-aminochroman intermediate have been studied as well as four methods for the construction of the 2-aminoethyl imidazolethione fragment. The evolution of the synthetic strategy based on the early discovery route was described. By focusing on the use of readily available starting materials it was possible to avoid chromatography steps and expensive reagents, bringing about significant improvements in cost and throughput. The best route involves construction of the chiral centre by asymmetric hydrogenation.