ethyl α-hydroxy-α-(4-aminophenyl)-α-phenylacetate | 81039-78-3

• 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: ethyl α-hydroxy-α-(4-aminophenyl)-α-phenylacetate
• 英文别名: 4-Aminobenzilic Acid Ethyl Ester；ethyl 2-(4-aminophenyl)-2-hydroxy-2-phenylacetate
• CAS: 81039-78-3
• 化学式: C₁₆H₁₇NO₃
• 分子量: 271.316
• InChiKey: VTTPGJVNTMHGLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl α-hydroxy-α-(4-aminophenyl)-α-phenylacetate 在 甲烷磺酸 、 2,2,2-三氟乙醇 、 硫酸 、 sodium 、 sodium iodide 、 sodium nitrite 作用下， 以 水 、 丙酮 为溶剂， 反应 25.83h， 生成 3-奎宁环基 4-碘二苯羟乙酸酯
  参考文献：
  名称：

  Synthesis and evaluation of radioiodinated derivatives of 1-azabicyclo[2.2.2]oct-3-yl .alpha.-hydroxy-.alpha.-(4-iodophenyl)-.alpha.-phenylacetate as potential radiopharmaceuticals

  摘要：

  Two derivatives of (RS)-1-azabicyclo[2.2.2]oct-3-yl (RS)-alpha-hydroxy-alpha-(4-iodophenyl)-alpha-phenylacetate (1a) and three partially resolved (R)- or (S)-1-azabicyclo[2.2.2]oct-3-yl (RS)-alpha-hydroxy-alpha-(4-iodophenyl)-alpha-phenylacetates labeled with no carrier added iodine-125 (1b, 18, and 19) and iodine-123 (1c and 18a) were synthesized by the Wallach triazene approach. We have found that this approach is necessary to obtain no carrier added labeling and gives far better results than the direct electrophilic iodination. The obtained yields were 7 to 18% when using iodine-123 (yield dependent on the source of iodide) and up to 17% for iodine-123 (yield dependent on the source of iodide) and up to 17% for iodine-125 labeled compounds. Our preliminary distribution studies indicate that 1b localizes in the organs known to have a large concentration of muscarinic receptors and that this localization is due to binding to those receptors.

  DOI：

  10.1021/jm00368a009
• 作为产物：
  描述：

  1-(4-氨基苯基)-2-苯基乙烷-1,2-二酮 在 盐酸 、 sodium hydroxide 作用下， 反应 29.0h， 生成 ethyl α-hydroxy-α-(4-aminophenyl)-α-phenylacetate
  参考文献：
  名称：

  Synthesis and evaluation of radioiodinated derivatives of 1-azabicyclo[2.2.2]oct-3-yl .alpha.-hydroxy-.alpha.-(4-iodophenyl)-.alpha.-phenylacetate as potential radiopharmaceuticals

  摘要：

  Two derivatives of (RS)-1-azabicyclo[2.2.2]oct-3-yl (RS)-alpha-hydroxy-alpha-(4-iodophenyl)-alpha-phenylacetate (1a) and three partially resolved (R)- or (S)-1-azabicyclo[2.2.2]oct-3-yl (RS)-alpha-hydroxy-alpha-(4-iodophenyl)-alpha-phenylacetates labeled with no carrier added iodine-125 (1b, 18, and 19) and iodine-123 (1c and 18a) were synthesized by the Wallach triazene approach. We have found that this approach is necessary to obtain no carrier added labeling and gives far better results than the direct electrophilic iodination. The obtained yields were 7 to 18% when using iodine-123 (yield dependent on the source of iodide) and up to 17% for iodine-123 (yield dependent on the source of iodide) and up to 17% for iodine-125 labeled compounds. Our preliminary distribution studies indicate that 1b localizes in the organs known to have a large concentration of muscarinic receptors and that this localization is due to binding to those receptors.

  DOI：

  10.1021/jm00368a009

文献信息

• Gamma-emitting receptor-binding 3-quinuclidinyl glycolates; methods of
  申请人：Research Corporation

  公开号：US04431627A1

  公开（公告）日：1984-02-14

  Compounds of the formula: ##STR1## wherein R is aryl, alkyl, cycloalkyl, phenyl, cyclopentyl, cyclohexyl, a ligand containing Tc-99m in chelated form or a ligand capable of chelating Tc-99m; R.sub.1 is H or lower alkyl; X is in the ortho-, meta or para- position, and is selected from the group consisting of .sup.125 I, .sup.123 I, .sup.127 I, I, .sup.18 F, .sup.75 Br, .sup.77 Br, NH.sub.2, and ##STR2## wherein R.sub.2 is in the 2,3, or 4 position and is selected from the group consisting of H and lower alkyl, provided that when R is a ligand capable of chelating Tc-99m or containing Tc-99m in chelated form, X is not a radioisotope and may also be H or lower alkyl; Z.sup..crclbar. is an anion; or the free amine thereof; and denotes an asymmetric carbon atom.

  化合物的公式：##STR1## 其中R是芳基，烷基，环烷基，苯基，环戊基，环己基，含有Tc-99m螯合形式的配体或能够螯合Tc-99m的配体; R.sub.1为H或较低烷基; X在邻位、间位或对位，选择自群组，其中包括.sup.125 I、.sup.123 I、.sup.127 I、I、.sup.18 F、.sup.75 Br、.sup.77 Br、NH.sub.2和##STR2## 其中R.sub.2在2、3或4位，选择自群组，其中包括H和较低烷基，前提是当R是能够螯合Tc-99m或者含有Tc-99m螯合形式的配体时，X不是放射性同位素，也可以是H或较低烷基；Z.sup..crclbar.是一个阴离子；或者其自由胺；并表示一个不对称的碳原子。
• ECKELMAN, W. C.;REBA, R. C.;RZESZOTARSKI, W. J.;GIBSON, R. E.
  作者：ECKELMAN, W. C.、REBA, R. C.、RZESZOTARSKI, W. J.、GIBSON, R. E.

  DOI：——

  日期：——
• GAMMA-EMITTING RECEPTOR-BINDING QUINUCLIDINYL BENZILATES METHODS OF PREPARATION THEREOF AND IMAGING AND ASSAY METHODS UTILIZING SAME
  申请人：Research Corporation

  公开号：EP0052645B1

  公开（公告）日：1987-05-13
• EP0052645A4
  申请人：——

  公开号：EP0052645A4

  公开（公告）日：1983-03-29
• GAMMA-EMITTING RECEPTOR-BINDING 3-QUINUCLIDINYL GLYCOLATES: METHODS OF PREPARATION THEREOF AND IMAGING AND ASSAY METHODS UTILIZING SAME
  申请人：Research Corporation

  公开号：EP0097647A1

  公开（公告）日：1984-01-11