(R,S)-α-hydroxy-α-(4-nitrophenyl)-α-phenylacetic acid | 88000-54-8

• 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: (R,S)-α-hydroxy-α-(4-nitrophenyl)-α-phenylacetic acid
• 英文别名: α-hydroxy-α-(4-nitrophenyl)-α-phenylacetic acid；Hydroxy(4-nitrophenyl)phenylacetic acid；2-hydroxy-2-(4-nitrophenyl)-2-phenylacetic acid
• CAS: 88000-54-8
• 化学式: C₁₄H₁₁NO₅
• 分子量: 273.245
• InChiKey: VYXVBJKVHSLTKO-UHFFFAOYSA-N

物化性质

• 沸点：
  496.5±45.0 °C(Predicted)
• 密度：
  1.436±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R,S)-α-hydroxy-α-(4-nitrophenyl)-α-phenylacetic acid 在 Pd-polyethylamine 二环己烷并-18-冠醚-6 、 甲烷磺酸 、 2,2,2-三氟乙醇 、 硫酸 、 氢气 、 sodium 、 potassium carbonate 、 sodium iodide 、 sodium nitrite 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 25.0 ℃ 、303.98 kPa 条件下， 反应 146.33h， 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：

  4-硝基二苯甲酮 在 盐酸 、 zinc(II) iodide 作用下， 以 二氯甲烷 为溶剂， 反应 96.0h， 生成 (R,S)-α-hydroxy-α-(4-nitrophenyl)-α-phenylacetic acid
  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

• Preparation and Properties of (R)-(−)-1-Azabicyclo[2.2.2]Oct-3-yl-(R)-(+)-α-Hydroxy-α-(4-[125l]Iodophenyl)-α-Phenyl Acetate and (R)-(−)-1-Azabicyclo[2.2.2]Oct-3-Yl-(S)-(−)-α-hydroxy-α-(4-[125l]iodophenyl)-α-phenyl acetate as potential radiopharmaceuticals
  作者：Victor I. Cohien、Waclaw J. Rzeszotarski、Raymond E. Gibson、Linda H. Fan、Richard C. Reba

  DOI：10.1002/jps.2600781011

  日期：1989.10

  alpha-phenyl acetate. After hydrogenation, the (R,R)- and (R,S)-amines were converted to the respective triazene derivatives. The triazene derivatives reacted with sodium [125I]iodide to give (R)-(-)-1-azabicyclo[2.2.2]oct-3-yl-(R)-(+)- alpha-hydroxy-alpha-(4-[125I]iodophenyl)-alpha-phenyl acetate and (R)-(-)-1-azabicyclo[2.2.2]oct-3-yl-(S)-(-)-alpha-hydroxy- alpha-(4-[125I]iodophenyl)-alpha-phenyl

  合成了rac-4-硝基苯甲酸，并用奎尼丁和奎宁拆分，得到相应的（R）-和（S）-盐。将拆分的非对映异构体盐转化为（R）-和（S）-4-硝基苯甲酸，随后酯化得到其相应的乙酯。与（R）-（-）-3-奎宁环醇酯交换反应得到（R）-（-）-1-氮杂双环[2.2.2] oct-3-yl-（R）-（+）-α-羟基-α- （4-硝基苯基）-α-苯基乙酸酯和（R）-（-）-1-氮杂双环[2.2.2] oct-3-yl-（S）-（-）-α-羟基-α-（4-硝基苯基）-α-苯基乙酸酯 氢化后，将（R，R）-和（R，S）-胺转化为相应的三氮烯衍生物。三嗪衍生物与[125I]碘化钠反应，得到（R）-（-）-1-氮杂双环[2.2.2] oct-3-yl-（R）-（+）-α-羟基-α-（4 -[125I]碘苯基）-α-乙酸苯酯和（R）-（-）-1-氮杂双环[2.2。2]辛-3-基-（S）-（-）-α-羟基-α-（4-
• Boronic acid adducts of rhenium dioxime and technetium-99M dioxime complexes containing a biochemically active group
  申请人：BRACCO INTERNATIONAL B.V.

  公开号：EP0441491A1

  公开（公告）日：1991-08-14

  Boronic acid adducts of technetium-99m and radioactive rhenium dioxime complexes, each of which include biochemically active groups, are useful as diagnostic and therapeutic agents, respectively.

  锝-99m 的硼酸加合物和放射性二氧化铼络合物都含有生化活性基团，可分别用作诊断和治疗药物。
• Toda, Fumio; Tanaka, Koichi; Kagawa, Yukiko, Chemistry Letters, 1990, # 3, p. 373 - 376
  作者：Toda, Fumio、Tanaka, Koichi、Kagawa, Yukiko、Sakaino, Yoshiko

  DOI：——

  日期：——
• TODA, FUMIO;TANAKA, KOICHI;KAGAWA, YUKIKO;SAKAINO, YOSHIKO, CHEM. LETT.,(1990) N, C. 373-376
  作者：TODA, FUMIO、TANAKA, KOICHI、KAGAWA, YUKIKO、SAKAINO, YOSHIKO

  DOI：——

  日期：——
• IKEDA, YOSHIKAZU;MANDA, EIICHIRO, BULL. CHEM. SOC. JAP., 1985, 58, N 6, 1723-1726
  作者：IKEDA, YOSHIKAZU、MANDA, EIICHIRO

  DOI：——

  日期：——