2,4-dimethylpentan-3-yl 4-bromo-2-fluorobenzoate

• 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: 2,4-dimethylpentan-3-yl 4-bromo-2-fluorobenzoate
• 英文别名: 2,4-Dimethylpentan-3-yl 4-bromo-2-fluorobenzoate
• 化学式: C₁₄H₁₈BrFO₂
• 分子量: 317.198
• InChiKey: FLEMGJMJPBZYQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,4-dimethylpentan-3-yl 4-bromo-2-fluorobenzoate 在 sodium hydride 、 potassium hydroxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 8.0h， 生成 (-)-3-menthoxybiphenyl-4-carboxylic acid
  参考文献：
  名称：

  3-Menthoxybiphenyl-4-carboxylic acid: a versatile resolving agent and reagent for determination of the absolute configuration of benzylic alcohols

  摘要：

  A versatile reagent for the chiral resolution and determination of the absolute configuration of benzylic alcohols, (-)-3-menthoxybiphenyl-4-carboxylic acid, is reported. (-)-3-menthoxybiphenyl-4-carboxylic acid was condensed with racemic benzylic alcohols to yield diastereomeric 3-menthoxybiphenyl-4-carboxylic esters, which were separated by reversed-phase HPLC. The absolute configurations of the 3-menthoxybiphenyl-4-carboxylic esters were unambiguously determined by exciton-coupled circular dichroism. Hydrolysis of the 3-menthoxybiphenyl-4-carboxylic esters yielded enantiopure alcohols, and their absolute configurations were simultaneously determined. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2017.05.008
• 作为产物：
  描述：

  2,4-二甲基-3-戊醇 、 4-溴-2-氟苯甲酸 在 4-二甲氨基吡啶 、 混旋樟脑磺酸 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以97%的产率得到2,4-dimethylpentan-3-yl 4-bromo-2-fluorobenzoate
  参考文献：
  名称：

  3-Menthoxybiphenyl-4-carboxylic acid: a versatile resolving agent and reagent for determination of the absolute configuration of benzylic alcohols

  摘要：

  A versatile reagent for the chiral resolution and determination of the absolute configuration of benzylic alcohols, (-)-3-menthoxybiphenyl-4-carboxylic acid, is reported. (-)-3-menthoxybiphenyl-4-carboxylic acid was condensed with racemic benzylic alcohols to yield diastereomeric 3-menthoxybiphenyl-4-carboxylic esters, which were separated by reversed-phase HPLC. The absolute configurations of the 3-menthoxybiphenyl-4-carboxylic esters were unambiguously determined by exciton-coupled circular dichroism. Hydrolysis of the 3-menthoxybiphenyl-4-carboxylic esters yielded enantiopure alcohols, and their absolute configurations were simultaneously determined. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2017.05.008

文献信息

• 3-Menthoxybiphenyl-4-carboxylic acid: a versatile resolving agent and reagent for determination of the absolute configuration of benzylic alcohols
  作者：Shunsuke Kuwahara、Nobuyoshi Tasaki、Yuri Suzuki、Mizuki Nakagawa、Mari Ikeda、Yoichi Habata

  DOI：10.1016/j.tetasy.2017.05.008

  日期：2017.7

  A versatile reagent for the chiral resolution and determination of the absolute configuration of benzylic alcohols, (-)-3-menthoxybiphenyl-4-carboxylic acid, is reported. (-)-3-menthoxybiphenyl-4-carboxylic acid was condensed with racemic benzylic alcohols to yield diastereomeric 3-menthoxybiphenyl-4-carboxylic esters, which were separated by reversed-phase HPLC. The absolute configurations of the 3-menthoxybiphenyl-4-carboxylic esters were unambiguously determined by exciton-coupled circular dichroism. Hydrolysis of the 3-menthoxybiphenyl-4-carboxylic esters yielded enantiopure alcohols, and their absolute configurations were simultaneously determined. (C) 2017 Elsevier Ltd. All rights reserved.