2-(difluoromethyl)-2-hydroxypropionic acid | 1869-40-5

• 物质功能分类: 有机原料 - 有机氟化合物
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: 2-(difluoromethyl)-2-hydroxypropionic acid
• 英文别名: β,β-difluoro-α-hydroxy-isobutyric acid；β,β-Difluor-α-hydroxy-isobuttersaeure；3,3-Difluor-2-hydroxy-2-methyl-propionsaeure；3,3-difluoro-2-hydroxy-2-methyl propanoic acid；2-hydroxy-2-difluoromethylpropionic acid；3,3-difluoro-2-hydroxy-2-methylpropanoic acid
• CAS: 1869-40-5
• 化学式: C₄H₆F₂O₃
• mdl: MFCD19228764
• 分子量: 140.087
• InChiKey: IGCQAJNFEBAMJJ-UHFFFAOYSA-N

物化性质

• 熔点：
  87.5-88.5 °C
• 沸点：
  279.4±35.0 °C(Predicted)
• 密度：
  1.429±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(difluoromethyl)-2-hydroxypropionic acid 、 5-氨基-2-硝基三氟甲苯 在 氯化亚砜 、 异丁酰胺 作用下， 生成 3,3-difluoro-2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide
  参考文献：
  名称：

  Non-steroidal antiandrogens. Design of novel compounds based on an infrared study of the dominant conformation and hydrogen-bonding properties of a series of anilide antiandrogens

  摘要：

  Antiandrogenic activity is observed in anilides containing a tertiary hydroxyl group, and these compounds are used to define a pharmacophore in terms of their physicochemical properties. Infrared spectroscopy shows that these anilides exist in a single conformation, which exerts a powerful influence on the hydrogen-bond donor ability of the hydroxyl group in a model system. Arguments are presented which suggest that hydrogen-bonding ability is an important contributor to biological activity. Compounds were synthesized that reproduced these properties in series not containing an amide bond. Such compounds were found to exhibit good antiandrogen activity. We suggest that quantitative information on hydrogen bonding might also be useful in other systems.

  DOI：

  10.1021/jm00105a067
• 作为产物：
  描述：

  β,β-difluoro-α-hydroxy-isobutyronitrile 在 硫酸 作用下， 生成 2-(difluoromethyl)-2-hydroxypropionic acid
  参考文献：
  名称：

  Jakubowitsch et al., Zhurnal Obshchei Khimii, 1958, vol. 28, p. 2288,2291;engl.Ausg.S.2325,2327

  摘要：

  DOI：

文献信息

• Therapeutic amides
  申请人：Imperial Chemical Industries PLC

  公开号：US05272163A1

  公开（公告）日：1993-12-21

  Amides having formula I: ##STR1## wherein E, X, R.sup.2 and R.sup.3 have the meanings given in the specification, and pharmaceutically acceptable salts and pharmaceutically acceptable in vivo hydrolysable esters thereof, which are useful in the treatment of urinary incontinence. Further provided are processes for preparing the amides and pharmaceutical compositions containing them.

  酰胺具有以下化学式I：##STR1## 其中E、X、R.sup.2和R.sup.3的含义如规范中所述，并且其药学上可接受的盐和在体内可水解的酯，可用于治疗尿失禁。还提供了制备这些酰胺的方法和含有它们的药物组合物。
• MORRIS, JEFFREY J.;HUGHES, LESLIE R.;GLEN, ALASDAIR T.;TAYLOR, PETER J., J. MED. CHEM., 34,(1991) N, C. 447-455
  作者：MORRIS, JEFFREY J.、HUGHES, LESLIE R.、GLEN, ALASDAIR T.、TAYLOR, PETER J.

  DOI：——

  日期：——
• Jakubowitsch et al., Zhurnal Obshchei Khimii, 1958, vol. 28, p. 2288,2291;engl.Ausg.S.2325,2327
  作者：Jakubowitsch et al.

  DOI：——

  日期：——
• Non-steroidal antiandrogens. Design of novel compounds based on an infrared study of the dominant conformation and hydrogen-bonding properties of a series of anilide antiandrogens
  作者：Jeffrey J. Morris、Leslie R. Hughes、Alasdair T. Glen、Peter J. Taylor

  DOI：10.1021/jm00105a067

  日期：1991.1

  Antiandrogenic activity is observed in anilides containing a tertiary hydroxyl group, and these compounds are used to define a pharmacophore in terms of their physicochemical properties. Infrared spectroscopy shows that these anilides exist in a single conformation, which exerts a powerful influence on the hydrogen-bond donor ability of the hydroxyl group in a model system. Arguments are presented which suggest that hydrogen-bonding ability is an important contributor to biological activity. Compounds were synthesized that reproduced these properties in series not containing an amide bond. Such compounds were found to exhibit good antiandrogen activity. We suggest that quantitative information on hydrogen bonding might also be useful in other systems.