ethyl 2,2-difluoro-3-hydroxy-3-(4-methylthiophenyl)propanoate | 1042662-69-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: ethyl 2,2-difluoro-3-hydroxy-3-(4-methylthiophenyl)propanoate
• 英文别名: Ethyl 2,2-difluoro-3-hydroxy-3-(4-methylsulfanylphenyl)propanoate
• CAS: 1042662-69-0
• 化学式: C₁₂H₁₄F₂O₃S
• mdl: MFCD17964649
• 分子量: 276.304
• InChiKey: OWWUOZKACAHZJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 2,2-difluoro-3-hydroxy-3-(4-methylthiophenyl)propanoate 、 丙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 ethyl 2,2-difluoro-3-propionyloxy-3-(4-methylthiophenyl)propanoate
  参考文献：
  名称：

  Kinetic resolution of 2,2-difluoro-3-hydroxy-3-aryl-propionates catalyzed by organocatalyst (R)-benzotetramisole

  摘要：

  Kinetic resolution of a series of ethyl 2,2-difluoro-3-hydroxy-3-aryl-propionates catalyzed by (R)-benzotetramisole has been performed. It was found that when the aryl group was phenyl or phenyl substituted with electron-donating group (such as -Me, -OMe, and -SMe) or naphthyl groups, the enantio-selectivity factor (s) could reach 20 or higher; electron-withdrawing (such as fluorine) substitution on the benzene ring dramatically lowers the s value. Kinetic resolution in preparative scale for some of the substrates demonstrated the applicability of this method. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.04.055
• 作为产物：
  描述：

  二氟溴乙酸乙酯 、 4-(甲基巯基)苯甲醛 在 锌 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 ethyl 2,2-difluoro-3-hydroxy-3-(4-methylthiophenyl)propanoate
  参考文献：
  名称：

  Kinetic resolution of 2,2-difluoro-3-hydroxy-3-aryl-propionates catalyzed by organocatalyst (R)-benzotetramisole

  摘要：

  Kinetic resolution of a series of ethyl 2,2-difluoro-3-hydroxy-3-aryl-propionates catalyzed by (R)-benzotetramisole has been performed. It was found that when the aryl group was phenyl or phenyl substituted with electron-donating group (such as -Me, -OMe, and -SMe) or naphthyl groups, the enantio-selectivity factor (s) could reach 20 or higher; electron-withdrawing (such as fluorine) substitution on the benzene ring dramatically lowers the s value. Kinetic resolution in preparative scale for some of the substrates demonstrated the applicability of this method. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.04.055

文献信息

• Kinetic resolution of 2,2-difluoro-3-hydroxy-3-aryl-propionates catalyzed by organocatalyst (R)-benzotetramisole
  作者：Hui Zhou、Qing Xu、Peiran Chen

  DOI：10.1016/j.tet.2008.04.055

  日期：2008.6

  Kinetic resolution of a series of ethyl 2,2-difluoro-3-hydroxy-3-aryl-propionates catalyzed by (R)-benzotetramisole has been performed. It was found that when the aryl group was phenyl or phenyl substituted with electron-donating group (such as -Me, -OMe, and -SMe) or naphthyl groups, the enantio-selectivity factor (s) could reach 20 or higher; electron-withdrawing (such as fluorine) substitution on the benzene ring dramatically lowers the s value. Kinetic resolution in preparative scale for some of the substrates demonstrated the applicability of this method. (c) 2008 Elsevier Ltd. All rights reserved.