(R)-α-hydroxy-α-(4-iodophenyl)benzeneacetate | 137820-95-2

• 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)-α-hydroxy-α-(4-iodophenyl)benzeneacetate
• 英文别名: (R)-α-hydroxy-α-(4-iodophenyl)-α-phenylacetic acid；(R)-4-iodobenzilic acid；(2R)-2-hydroxy-2-(4-iodophenyl)-2-phenylacetic acid
• CAS: 137820-95-2
• 化学式: C₁₄H₁₁IO₃
• 分子量: 354.144
• InChiKey: SKCUPWGUSRLOIX-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 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：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-α-hydroxy-α-(4-iodophenyl)benzeneacetate 、 (S)-(+)-3-喹宁醇 在 N,N'-羰基二咪唑 作用下， 生成 (S)-1-azabicyclo<2.2.2>-oct-3-yl-(R)-α-hydroxy-α-(4-iodophenyl)-α-phenylacetate
  参考文献：
  名称：

  Synthesis of the four stereoisomers of 1-azabicyclo[2.2.2]oct-3-yl-α-hydroxy-α-(4-phenylboronic acid)-α-phenylacetate (QNB-boronic acid), including a preparative HPLC method to separate diastereoisomeric mixtures with high optical purity

  摘要：

  The four stereoisomers of 1-azabicyclo[2.2.2]oct-3-yl-alpha-hydroxy-alpha-(4-phenylboronic acid)-alpha-phenylacetate (QNB boronic acids, 1a-1d) were synthesized initially via 1-azabicyclo[2.2.2]oct-3-yl-alpha hydroxy-alpha-(4-iodophenyl)-alpha-phenylacetate (iodo-QNBs, 6a-6d) using an adaptation of a published procedure. The number of steps involved were reduced substantially using a distinctly different approach. This involved the synthesis of diastereoisomers of QNB-boronic acid, followed by separation and isolation of enantiomers by preparative reversed-phase HPLC. An improved method of synthesis of alpha-hydroxy-alpha-(4-aminophenyl)-alpha-phenyl-acetic acid (3a and 3b) from alpha-hydroxy-alpha-(4-nitrophenyl)-alpha-phenylacetic acid (2a and 2b) is also described.

  DOI：

  10.1016/s0957-4166(00)82085-6
• 作为产物：
  描述：

  2-(4-iodophenyl)-2-oxoacetic acid 在 氢氧化钾 、 1,1-二氯甲醚 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 1,2-二氯乙烷 为溶剂， 反应 7.0h， 生成 (R)-α-hydroxy-α-(4-iodophenyl)benzeneacetate
  参考文献：
  名称：

  使用8-苯基薄荷醇作为手性助剂的苯甲酸类似物的不对称合成

  摘要：

  我们合成18 F-标记的毒蕈碱受体配体的程序需要制备手性氟烷基苯甲酸。使用8-苯基薄荷醇作为手性助剂，实现了对取代苯甲酸的对映选择性合成。在8-苯基薄荷基苯甲酰基甲酸酯7的si表面上进行格氏试剂以高选择性进行。手性诱导的结果支持先前通过结晶拆分的苯甲酸的手性分配。该方法用于合成（R）-奎宁环烷基-（R）-（4-碘）苯甲酸酯，事实证明与真实样品相同。另外，该方法允许以立体选择性的方式制备（R）-和（S）-氟乙基苯甲酸。

  DOI：

  10.1016/s0957-4166(00)80069-5

文献信息

• Boronic acid adducts of rhenium dioxime and technetium-99m dioxime
  申请人：Bracco International B.V.

  公开号：US05387409A1

  公开（公告）日：1995-02-07

  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.

  硼酸添加物和放射性重铼二氧化物络合物的锝-99m，每种均包含生化活性基团，分别用作诊断和治疗剂。
• 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。
• US5387409A
  申请人：——

  公开号：US5387409A

  公开（公告）日：1995-02-07
• Asymmetric synthesis of benzilic acid analogues using 8-phenylmenthol as a chiral auxiliary
  作者：Dale O. Kiesewetter

  DOI：10.1016/s0957-4166(00)80069-5

  日期：1993.10

  ligands required the preparation of chiral fluoroalkyl benzilic acids. An enantioselective synthesis of substituted benzilic acids was achieved using 8-phenylmenthol as the chiral auxiliary. Grignard addition to the si face of 8-phenylmenthyl benzoylformate 7 proceeded with high selectivity. The results of the chiral induction support assignments of the chirality of benzilic acids previously resolved

  我们合成18 F-标记的毒蕈碱受体配体的程序需要制备手性氟烷基苯甲酸。使用8-苯基薄荷醇作为手性助剂，实现了对取代苯甲酸的对映选择性合成。在8-苯基薄荷基苯甲酰基甲酸酯7的si表面上进行格氏试剂以高选择性进行。手性诱导的结果支持先前通过结晶拆分的苯甲酸的手性分配。该方法用于合成（R）-奎宁环烷基-（R）-（4-碘）苯甲酸酯，事实证明与真实样品相同。另外，该方法允许以立体选择性的方式制备（R）-和（S）-氟乙基苯甲酸。
• Synthesis of the four stereoisomers of 1-azabicyclo[2.2.2]oct-3-yl-α-hydroxy-α-(4-phenylboronic acid)-α-phenylacetate (QNB-boronic acid), including a preparative HPLC method to separate diastereoisomeric mixtures with high optical purity
  作者：P. Nanjappan、K. Ramalingam、D.J. Nowotnik

  DOI：10.1016/s0957-4166(00)82085-6

  日期：1992.10

  The four stereoisomers of 1-azabicyclo[2.2.2]oct-3-yl-alpha-hydroxy-alpha-(4-phenylboronic acid)-alpha-phenylacetate (QNB boronic acids, 1a-1d) were synthesized initially via 1-azabicyclo[2.2.2]oct-3-yl-alpha hydroxy-alpha-(4-iodophenyl)-alpha-phenylacetate (iodo-QNBs, 6a-6d) using an adaptation of a published procedure. The number of steps involved were reduced substantially using a distinctly different approach. This involved the synthesis of diastereoisomers of QNB-boronic acid, followed by separation and isolation of enantiomers by preparative reversed-phase HPLC. An improved method of synthesis of alpha-hydroxy-alpha-(4-aminophenyl)-alpha-phenyl-acetic acid (3a and 3b) from alpha-hydroxy-alpha-(4-nitrophenyl)-alpha-phenylacetic acid (2a and 2b) is also described.