benzyl 2,2-difluoropropionate | 134430-54-9

• 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: benzyl 2,2-difluoropropionate
• 英文别名: Benzyl 2,2-difluoropropanoate
• CAS: 134430-54-9
• 化学式: C₁₀H₁₀F₂O₂
• 分子量: 200.185
• InChiKey: IGFFUHQTQBUFKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-(+)-甲基对甲苯砜 、 benzyl 2,2-difluoropropionate 在 lithium diisopropyl amide 作用下， 生成 (R)-3,3-difluoro-1-<(4-methylphenyl)sulfinyl>butan-2-one 、 3,3-Difluoro-1-((R)-toluene-4-sulfinyl)-butane-2,2-diol
  参考文献：
  名称：

  Asymmetric synthesis of oxygen- and nitrogen-substituted difluoromethylene products

  摘要：

  1,1-Difluoroalkyl sulfinylmethyl ketones 3 are synthesized in enantiomerically pure form through acylation of (+)-(R)-methyl p-tolyl sulfoxide (1) with alpha,alpha-difluorocarboxylates 2. These ketones have been reduced with complete diastereoselection to give the corresponding alcohols. Removal of the auxiliary sulfinyl group and further elaborations afforded enantiomerically pure 2-(benzyloxy)-3,3-difluoro alcohols, esters, oximes, hydroxylamines, and nitriles.

  DOI：

  10.1021/jo00035a035
• 作为产物：
  描述：

  丙酸苄酯 在 双(三甲基硅烷基)氨基钾 、 N-fluorosaccharin 作用下， 生成 benzyl 2-fluoropropanoate 、 benzyl 2,2-difluoropropionate
  参考文献：
  名称：

  Selective mono- and difluorination of enolates

  摘要：

  The selective transformation of enolates into mono- and difluorinated carbonyl compounds can be performed in a one-pot procedure using N-F-sultam 1. The yields and the selectivity of the fluorination strongly depend on the counterion of the enolate and the acidity of the protons alpha to the carbonyl group.

  DOI：

  10.1016/s0040-4039(00)74328-0

文献信息

• Differding, E.; Frick, W.; Lang, R. W., Bulletin des Societes Chimiques Belges, 1990, vol. 99, # 9, p. 647 - 671
  作者：Differding, E.、Frick, W.、Lang, R. W.、Martin, P.、Schmit, C.、et al.

  DOI：——

  日期：——
• Asymmetric synthesis of oxygen- and nitrogen-substituted difluoromethylene products
  作者：Pierfrancesco Bravo、Massimo Pregnolato、Giuseppe Resnati

  DOI：10.1021/jo00035a035

  日期：1992.4

  1,1-Difluoroalkyl sulfinylmethyl ketones 3 are synthesized in enantiomerically pure form through acylation of (+)-(R)-methyl p-tolyl sulfoxide (1) with alpha,alpha-difluorocarboxylates 2. These ketones have been reduced with complete diastereoselection to give the corresponding alcohols. Removal of the auxiliary sulfinyl group and further elaborations afforded enantiomerically pure 2-(benzyloxy)-3,3-difluoro alcohols, esters, oximes, hydroxylamines, and nitriles.
• Selective mono- and difluorination of enolates
  作者：Edmond Differding、Gabriela M. Rüegg、Robert W. Lang

  DOI：10.1016/s0040-4039(00)74328-0

  日期：1991.4

  The selective transformation of enolates into mono- and difluorinated carbonyl compounds can be performed in a one-pot procedure using N-F-sultam 1. The yields and the selectivity of the fluorination strongly depend on the counterion of the enolate and the acidity of the protons alpha to the carbonyl group.