2,2-Difluoro-1-methoxy-2-phenylethanol | 144156-68-3

• 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: 2,2-Difluoro-1-methoxy-2-phenylethanol
• CAS: 144156-68-3
• 化学式: C₉H₁₀F₂O₂
• 分子量: 188.174
• InChiKey: MOEAKQJVVDKZRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2-Difluoro-1-methoxy-2-phenylethanol 在 盐酸 、 potassium dihydrogenphosphate 、 硫酸 作用下， 反应 7.0h， 生成 Ethyl 3,3-difluoro-2-hydroxy-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
• 作为产物：
  描述：

  二氟苯基乙酸甲酯 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 2,2-Difluoro-1-methoxy-2-phenylethanol
  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

• Asymmetric synthesis of β,β-difluoroamino acids via cross-coupling and Strecker reactions
  作者：Xiao-Jin Wang、Fan Zhang、Jin-Tao Liu

  DOI：10.1016/j.tet.2007.12.002

  日期：2008.2

  β,β-Difluoroamino acids were synthesized from commercially available ethyl bromodifluoroacetate using cross-coupling and Strecker reactions as key steps. The coupling reaction of aryl iodides with ethyl bromodifluoroacetate gave the corresponding coupling products, which were transformed to 2-difluoromethyl-1,3-oxazolidines in two steps. Boron trifluoride etherate promoted Strecker reaction of 2-difluoromethyl-1

  使用交叉偶联和Strecker反应作为关键步骤，由市售溴二氟乙酸乙酯合成β，β-二氟氨基酸。芳基碘化物与溴二氟乙酸乙酯的偶合反应得到相应的偶合产物，将其分两步转化为2-二氟甲基-1,3-恶唑烷。三氟化硼醚化物促进的2-二氟甲基-1,3-恶唑烷的Strecker反应产生了高产率和非对映选择性的α-氨基腈。除去手性助剂并水解腈基后，获得具有73％ee的β，β-二氟苯丙氨酸。在腈基水解过程中发生部分消旋。