3,3-Difluoro-2-hydroxypentanenitrile | 165544-29-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: 3,3-Difluoro-2-hydroxypentanenitrile
• CAS: 165544-29-6
• 化学式: C₅H₇F₂NO
• 分子量: 135.113
• InChiKey: ILSUAIJUHZKIHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,3-Difluoro-2-hydroxypentanenitrile 在 盐酸 、 硫酸 作用下， 反应 5.5h， 生成 Ethyl 3,3-difluoro-2-hydroxypentanoate
  参考文献：
  名称：

  Conversion of .alpha.-Keto Esters into .beta.,.beta.-Difluoro-.alpha.-keto Esters and Corresponding Acids: A Simple Route to a Novel Class of Serine Protease Inhibitors

  摘要：

  The preparation of a series of beta,beta-difluoro-alpha-keto esters and corresponding acids RCF(2)COCO(2)R' (R = Me, Et; i-Pr, Bn, and Ph; R' = Et and H), designed as potential inhibitors of serine proteases, is described. The standard procedure developed consists in the initial formation of an alpha,alpha-difluoro ester from an alpha-keto ester, followed by a simple four-step sequence involving the synthesis of hemiacetal, cyanohydrin, and alpha-hydroxy ester difluorinated intermediates. This method provides an easy route to beta,beta-difluoro-alpha-keto esters and corresponding acids, via ''formal'' insertion of a difluoromethylene group between the R substituent and the alpha-carbonyl group of a generic alpha-keto ester.

  DOI：

  10.1021/jo00121a040
• 作为产物：
  描述：

  氰化钾 、 2,2-Difluoro-1-methoxy-1-butanol 在 potassium dihydrogenphosphate 作用下， 反应 1.5h， 生成 3,3-Difluoro-2-hydroxypentanenitrile
  参考文献：
  名称：

  Conversion of .alpha.-Keto Esters into .beta.,.beta.-Difluoro-.alpha.-keto Esters and Corresponding Acids: A Simple Route to a Novel Class of Serine Protease Inhibitors

  摘要：

  The preparation of a series of beta,beta-difluoro-alpha-keto esters and corresponding acids RCF(2)COCO(2)R' (R = Me, Et; i-Pr, Bn, and Ph; R' = Et and H), designed as potential inhibitors of serine proteases, is described. The standard procedure developed consists in the initial formation of an alpha,alpha-difluoro ester from an alpha-keto ester, followed by a simple four-step sequence involving the synthesis of hemiacetal, cyanohydrin, and alpha-hydroxy ester difluorinated intermediates. This method provides an easy route to beta,beta-difluoro-alpha-keto esters and corresponding acids, via ''formal'' insertion of a difluoromethylene group between the R substituent and the alpha-carbonyl group of a generic alpha-keto ester.

  DOI：

  10.1021/jo00121a040