N-(benzyl-5-tert-butyl-2-hydroxy)phenylglycine | 197004-98-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(benzyl-5-tert-butyl-2-hydroxy)phenylglycine
• 英文别名: 2-(Benzylamino)-2-(5-tert-butyl-2-hydroxyphenyl)acetic acid
• CAS: 197004-98-1
• 化学式: C₁₉H₂₃NO₃
• 分子量: 313.397
• InChiKey: UQWWYSKPKBBGSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(benzyl-5-tert-butyl-2-hydroxy)phenylglycine 在 盐酸 、 过氧乙酸 、 sodium iodide 作用下， 反应 0.05h， 以53%的产率得到[123I]-N-benzyl-(5-tert-butyl-2-hydroxy-3-iodo)phenylglycine
  参考文献：
  名称：

  Synthesis, attempted kinetic resolution and evaluation of [123I]-MK-447 analogues as inflammation radiopharmaceuticals

  摘要：

  The non-steroidal anti-inflammatory agent 2-amino-methyl-4-tert-butyl-6-iodophenol hydrochloride (MK-447) and some of its analogues were labelled with I-123 and tested in an inflamed rat-paw model. Even though MK-447 has a significant anti-inflammatory activity, and a 2.3 ratio for inflamed site over muscle, its usefullness for scintigraphic detection of inflammation is hindered by its high uptake in the skin. The kinetic resolution of diastereomeric products with chiral dienyl iron complexes was unsuccessful as the signals from the respective H-1 and C-13 NMR spectra were coincident.

  DOI：

  10.1002/(sici)1099-1344(199709)39:9<711::aid-jlcr22>3.0.co;2-a
• 作为产物：
  描述：

  4-叔丁基苯酚 、 乙醛酸 、 苄胺 在 sodium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 6.0h， 以57%的产率得到N-(benzyl-5-tert-butyl-2-hydroxy)phenylglycine
  参考文献：
  名称：

  摘要：

  A series of tridentate ligands, N-benzyl-2-(2-hydroxyphenyl)glycines (bhpg) (4), were prepared by the Mannich reaction of phenol and a number of para-substituted phenols with glyoxylic acid and benzylamine. When the two ortho positions of the phenol were blocked, as in the case of 2,6-dimethyl and 2,6-dichloro phenols, the isomeric compounds N-benzyl-2-(4-hydroxyphenyl)glycines (isobhpg) (5) were formed. When the phenol had one ortho substituent, as in the case of o-cresol and o-chlorophenol, both isomers were isolated. Two examples of the use of the chiral alpha -phenylethylamine in place of benzylamine are described.

  DOI：

  10.1071/ch00054