Methyl 2,2-difluoro-3-phenylpropanoate | 109872-99-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Methyl 2,2-difluoro-3-phenylpropanoate
• 英文别名: alpha,alpha-Difluorobenzenepropionic acid methyl ester
• CAS: 109872-99-3
• 化学式: C₁₀H₁₀F₂O₂
• 分子量: 200.185
• InChiKey: WSIXROKHAGVIKQ-UHFFFAOYSA-N

物化性质

• 沸点：
  230.7±40.0 °C(Predicted)
• 密度：
  1.179±0.06 g/cm3(Predicted)

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：

  Methyl 2,2-difluoro-3-phenylpropanoate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.5h， 生成 2,2-Difluoro-1-methoxy-3-phenyl-1-propanol
  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：

  2-氧代-3-苯基丙酸甲酯 在 (diethylamido)sulfur trifluoride 作用下， 反应 1.0h， 以43%的产率得到Methyl 2,2-difluoro-3-phenylpropanoate
  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

文献信息

• (Methyl Difluoroacetate)copper Reagent. Remarkable Solvent Effect on the¹⁹F-NMR Spectrum, Stability and Reactivity
  作者：Osamu Kitagawa、Takeo Taguchi、Yoshiro Kobayashi

  DOI：10.1246/cl.1989.389

  日期：1989.3

  The 19F-NMR spectrum, thermal stability and reactivity of (methyl difluoroacetate)copper reagent were found to differ remarkably depending on the solvent (DMSO, DMF, or HMPA) used. With allylic bromide or alkynyl halide a crucial solvent effect for the coupling reactions was observed.

  发现（二氟乙酸甲酯）铜试剂的 19 F-NMR 光谱、热稳定性和反应性因所使用的溶剂（DMSO、DMF 或 HMPA）而异。对于烯丙基溴或炔基卤化物，观察到偶联反应的关键溶剂效应。
• Synthesis of 2,2-difluoroesters by iododifluoroacetate-copper with organic halides
  作者：Takeo Taguchi、Osamu Kitagawa、Tsutomu Morikawa、Tohru Nishiwaki、Hideya Uehara、Hatsumi Endo、Yoshiro Kobayashi

  DOI：10.1016/s0040-4039(00)85409-x

  日期：1986.1
• US3931279A
  申请人：——

  公开号：US3931279A

  公开（公告）日：1976-01-06
• US4138576A
  申请人：——

  公开号：US4138576A

  公开（公告）日：1979-02-06
• US4138577A
  申请人：——

  公开号：US4138577A

  公开（公告）日：1979-02-06