3-奎宁环基 4-碘二苯羟乙酸酯 | 81381-93-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-奎宁环基 4-碘二苯羟乙酸酯
• 中文别名: 3-奎宁环基4-碘二苯羟乙酸酯；1-氮杂二环[2.2.2]辛-3-基羟基(4-碘苯基)苯基乙酸酯
• 英文名称: IQNB
• 英文别名: 3-Quinuclidinyl-4-iodobenzilate；1-azabicyclo[2.2.2]octan-3-yl 2-hydroxy-2-(4-iodophenyl)-2-phenylacetate
• CAS: 81381-93-3
• 化学式: C₂₁H₂₂INO₃
• 分子量: 463.315
• InChiKey: MHBGDNWDRYOZPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  二苯乙醇酸-3-奎宁环酯	quinuclidinyl benzilate	6581-06-2	C21H23NO3	337.419
  ——	(RS)-1-azabicyclo<2.2.2>oct-3-yl (RS)-α-hydroxy-α-(4-aminophenyl)-α-phenylacetate	81039-90-9	C21H24N2O3	352.433
  ——	(RS)-1-azabicyclo<2.2.2>oct-3-yl (RS)-α-hydroxy-α-<4-<2-(3-methylpiperidin-1-yl)-1,2-diazaethylen-1-yl>phenyl>-α-phenylacetate	81381-92-2	C27H34N4O3	462.592
  ——	ethyl α-hydroxy-α-(4-aminophenyl)-α-phenylacetate	81039-78-3	C16H17NO3	271.316

反应信息

• 作为产物：
  描述：

  二苯乙醇酸-3-奎宁环酯 在 碘 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 以57%的产率得到3-奎宁环基 4-碘二苯羟乙酸酯
  参考文献：
  名称：

  A DIRECT IODINATION METHOD WITH IODINE AND SILVER TRIFLATE FOR THE SYNTHESIS OF SPECT AND PET IMAGING AGENT PRECURSORS

  摘要：

  A direct iodination method with iodine and silver triflate for the synthesis of SPECT and PET imaging agent precursors has been developed.

  DOI：

  10.1081/scc-100105877

文献信息

• Analogs of 3-quinuclidinyl benzilate
  作者：W. J. Rzeszotarski、R. E. Gibson、W. C. Eckelman、D. A. Simms、E. M. Jagoda、N. L. Ferreira、R. C. Reba

  DOI：10.1021/jm00351a020

  日期：1982.9

  dog ventricular muscle measured. We have determined that the muscarinic receptor can to a different degree accommodate either a halogen in the ortho, meta, or para position of one phenyl ring or the replacement of one phenyl ring with an alkyl group. Our in vitro competition studies show that the affinities lie within a 270-fold range, from the highest affinity compound, 3-quinuclidinyl alpha-hydro

  已经合成了许多3-奎宁环烷基苯磺酸盐（QNB）的类似物，并测量了它们与来自大鼠或狗心室肌的毒蕈碱受体的亲和力。我们已经确定毒蕈碱受体可以在不同程度上容纳一个苯环的邻位，间位或对位中的卤素或一个烷基取代一个苯环。我们的体外竞争研究表明，亲和力处于270倍范围内，从亲和力最高的化合物3-奎宁环烯基α-羟基-α-环戊基苯基乙酸酯（2）到亲和力最低的化合物3-奎宁环烷基α-羟基- α-2-炔丙基苯基乙酸酯（11）。
• 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
  作者：W. J. Rzeszotarski、W. C. Eckelman、B. E. Francis、D. A. Simms、R. E. Gibson、E. M. Jagoda、M. P. Grissom、R. R. Eng、J. J. Conklin、R. C. Reba

  DOI：10.1021/jm00368a009

  日期：1984.2

  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.
• 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：——
• EP0648130A4
  申请人：——

  公开号：EP0648130A4

  公开（公告）日：1994-01-26
• RADIOIODINATED BENZOVESAMICOL ANALOGS FOR CHOLINERGIC NERVE MAPPING
  申请人：THE UNIVERSITY OF MICHIGAN

  公开号：EP0648130B1

  公开（公告）日：1998-12-30