4-bromo-1-chloro-2-((4-ethoxyphenyl)(isopropoxy)methyl)benzene | 1520113-13-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-bromo-1-chloro-2-((4-ethoxyphenyl)(isopropoxy)methyl)benzene
• CAS: 1520113-13-6
• 化学式: C₁₈H₂₀BrClO₂
• 分子量: 383.713
• InChiKey: LRYHAYMVFDABNW-UHFFFAOYSA-N

物化性质

• 熔点：
  54.2 °C
• 沸点：
  423.9±45.0 °C(predicted)
• 密度：
  1.302±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.02
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  magnesium,ethoxybenzene,bromide 在 硫酸 作用下， 以 2-甲基四氢呋喃 为溶剂， 反应 21.0h， 生成 4-bromo-1-chloro-2-((4-ethoxyphenyl)(isopropoxy)methyl)benzene
  参考文献：
  名称：

  Commercial Route Research and Development for SGLT2 Inhibitor Candidate Ertugliflozin

  摘要：

  A practical synthesis of SGLT2 inhibitor candidate ertugliflozin (1) has been developed for potential commercial application. The highly telescoped process involves only three intermediate isolations over a 12-step sequence. The dioxabicyclo[3.2.1]octane motif is prepared from commercially available 2,3,4,6-tetra-O-benzyl-D-glucose, with nucleophilic hydroxymethylation of a 5-ketogluconamide intermediate as a key step. The aglycone moiety is introduced via aryl anion, addition to a methylpiperazine amide. High chemical purity of the API is assured through isolation of the crystalline penultimate intermediate, tetraacetate 39. A cocrystalline complex of the amorphous solid 1 with L-pyroglutamic acid has been prepared in order to improve the physical properties for manufacture and to ensure robust API quality.

  DOI：

  10.1021/op4002802