9-Iodo-10-phenanthroic acid | 172878-81-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 9-Iodo-10-phenanthroic acid
• 英文别名: 9-Phenanthrenecarboxylic acid, 10-iodo-；10-iodophenanthrene-9-carboxylic acid
• CAS: 172878-81-8
• 化学式: C₁₅H₉IO₂
• 分子量: 348.14
• InChiKey: UKKAPGQHTOHGKB-UHFFFAOYSA-N

物化性质

• 沸点：
  482.4±28.0 °C(Predicted)
• 密度：
  1.810±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9-Iodo-10-phenanthroic acid 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 24.0h， 以79%的产率得到9-Iodoso-10-phenanthroic acid
  参考文献：
  名称：

  9-Iodoso-10-phenanthroate: Structure and Phosphorolytic Properties of a Nonplanar Iodoxolone

  摘要：

  9-Iodoso-10-phenanthroic acid (IPA-OK) was prepared from 9-cyanophenanthrene in a four-step, 44% overall yield synthesis, featuring cyano-directed ortho lithiation/iodination as the key step. An X-ray crystal structure showed that TPA-OH exists in a phenanthroiodoxol-3(1H)-one valence tautomeric form, 14-OH, characterized by T-shaped geometry at iodine, strong WO steric interactions between the peri-H atoms and the carbonyl and iodoso oxygen atoms, a ''short'' endocyclic I-O bond, well-differentiated carbonyl and endocyclic C-O bond lengths, and nonplanarity in both the iodoxolone and phenanthrene rings (Figures 1 and 2). IPA-OH was an excellent catalyst for the cleavage of p-nitrophenyl diphenyl phosphate (PNPDPP) in aqueous micellar cetyltrimethylammonium chloride (CTACl) solutions at pH 8 and 25 degrees C: 1 x 10(-5) M PNPDPP was cleaved by 1 x 10(-4) M IPA-OH in 3.5 x 10(-4) M CTACl with k(psi) = 0.38 s(-1). Experiments in which [PNPDPP] > [IPA-OH] demonstrated that the catalyst ''turned over''; hydrolysis of the putative phosphorylated IPA-OH intermediate was rapid.

  DOI：

  10.1021/jo00129a012
• 作为产物：
  描述：

  9-腈菲 在 2,2,6,6-四甲基哌啶 、 硫酸 、 甲基锂 、 碘 、 sodium nitrite 作用下， 以 四氢呋喃 、 乙醚 、 溶剂黄146 、 乙腈 为溶剂， 反应 19.0h， 生成 9-Iodo-10-phenanthroic acid
  参考文献：
  名称：

  9-Iodoso-10-phenanthroate: Structure and Phosphorolytic Properties of a Nonplanar Iodoxolone

  摘要：

  9-Iodoso-10-phenanthroic acid (IPA-OK) was prepared from 9-cyanophenanthrene in a four-step, 44% overall yield synthesis, featuring cyano-directed ortho lithiation/iodination as the key step. An X-ray crystal structure showed that TPA-OH exists in a phenanthroiodoxol-3(1H)-one valence tautomeric form, 14-OH, characterized by T-shaped geometry at iodine, strong WO steric interactions between the peri-H atoms and the carbonyl and iodoso oxygen atoms, a ''short'' endocyclic I-O bond, well-differentiated carbonyl and endocyclic C-O bond lengths, and nonplanarity in both the iodoxolone and phenanthrene rings (Figures 1 and 2). IPA-OH was an excellent catalyst for the cleavage of p-nitrophenyl diphenyl phosphate (PNPDPP) in aqueous micellar cetyltrimethylammonium chloride (CTACl) solutions at pH 8 and 25 degrees C: 1 x 10(-5) M PNPDPP was cleaved by 1 x 10(-4) M IPA-OH in 3.5 x 10(-4) M CTACl with k(psi) = 0.38 s(-1). Experiments in which [PNPDPP] > [IPA-OH] demonstrated that the catalyst ''turned over''; hydrolysis of the putative phosphorylated IPA-OH intermediate was rapid.

  DOI：

  10.1021/jo00129a012

文献信息

• 9-Iodoso-10-phenanthroate: Structure and Phosphorolytic Properties of a Nonplanar Iodoxolone
  作者：Robert A. Moss、Kathryn Bracken、T. J. Emge

  DOI：10.1021/jo00129a012

  日期：1995.12

  9-Iodoso-10-phenanthroic acid (IPA-OK) was prepared from 9-cyanophenanthrene in a four-step, 44% overall yield synthesis, featuring cyano-directed ortho lithiation/iodination as the key step. An X-ray crystal structure showed that TPA-OH exists in a phenanthroiodoxol-3(1H)-one valence tautomeric form, 14-OH, characterized by T-shaped geometry at iodine, strong WO steric interactions between the peri-H atoms and the carbonyl and iodoso oxygen atoms, a ''short'' endocyclic I-O bond, well-differentiated carbonyl and endocyclic C-O bond lengths, and nonplanarity in both the iodoxolone and phenanthrene rings (Figures 1 and 2). IPA-OH was an excellent catalyst for the cleavage of p-nitrophenyl diphenyl phosphate (PNPDPP) in aqueous micellar cetyltrimethylammonium chloride (CTACl) solutions at pH 8 and 25 degrees C: 1 x 10(-5) M PNPDPP was cleaved by 1 x 10(-4) M IPA-OH in 3.5 x 10(-4) M CTACl with k(psi) = 0.38 s(-1). Experiments in which [PNPDPP] > [IPA-OH] demonstrated that the catalyst ''turned over''; hydrolysis of the putative phosphorylated IPA-OH intermediate was rapid.