3-[(tert-butoxycarbonyl)amino]-5-iodobenzoic acid | 337973-06-5

• 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: 3-[(tert-butoxycarbonyl)amino]-5-iodobenzoic acid
• 英文别名: 3-iodo-5-[(2-methylpropan-2-yl)oxycarbonylamino]benzoic acid
• CAS: 337973-06-5
• 化学式: C₁₂H₁₄INO₄
• 分子量: 363.152
• InChiKey: QOEAINLHQUJKAU-UHFFFAOYSA-N

物化性质

• 沸点：
  401.3±40.0 °C(Predicted)
• 密度：
  1.704±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[(tert-butoxycarbonyl)amino]-5-iodobenzoic acid 在 4-二甲氨基吡啶 、 palladium diacetate 、 sodium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 2-trimethylsilylethyl 3-[(2-methylpropan-2-yl)oxycarbonylamino]-5-(3-nitrophenyl)benzoate
  参考文献：
  名称：

  Rigid Macrocyclic Triamides as Anion Receptors:  Anion-Dependent Binding Stoichiometries and ¹H Chemical Shift Changes

  摘要：

  The cyclic triamide of 3'-amino-3-biphenylcarboxlic acid is readily synthesized in a stepwise manner and represents a novel class of anion receptors with a large central cavity. This macrocycle binds more strongly to tetrahedral anions than spherical or planar anions in organic solvents. The binding stoichiometries for anions with symmetrical charge distribution depend on the solvent polarity, while tetrahedral p-tosylate binds to the macrocycle with 1:1 stoichiometry in all solvents studied. The H-1 NMR chemical shift changes of the protons lining the interior of the macrocycle's central cavity also depend on the geometry of the bound anion. The importance of the convergent array of hydrogen bond donors for anion binding by the macrocycle was confirmed by control studies with an acyclic triamide and a macrocycle with intramolecular hydrogen bonds.

  DOI：

  10.1021/ja034563x
• 作为产物：
  描述：

  3-碘-5-硝基苯甲酸 在 ferrous ammonium sulphate 、 ammonium hydroxide 作用下， 以 1,4-二氧六环 、 氢氧化钾 为溶剂， 反应 0.17h， 生成 3-[(tert-butoxycarbonyl)amino]-5-iodobenzoic acid
  参考文献：
  名称：

  Rigid Macrocyclic Triamides as Anion Receptors:  Anion-Dependent Binding Stoichiometries and ¹H Chemical Shift Changes

  摘要：

  The cyclic triamide of 3'-amino-3-biphenylcarboxlic acid is readily synthesized in a stepwise manner and represents a novel class of anion receptors with a large central cavity. This macrocycle binds more strongly to tetrahedral anions than spherical or planar anions in organic solvents. The binding stoichiometries for anions with symmetrical charge distribution depend on the solvent polarity, while tetrahedral p-tosylate binds to the macrocycle with 1:1 stoichiometry in all solvents studied. The H-1 NMR chemical shift changes of the protons lining the interior of the macrocycle's central cavity also depend on the geometry of the bound anion. The importance of the convergent array of hydrogen bond donors for anion binding by the macrocycle was confirmed by control studies with an acyclic triamide and a macrocycle with intramolecular hydrogen bonds.

  DOI：

  10.1021/ja034563x

文献信息

• Design, chemical synthesis, and in vitro biological evaluation of simplified estradiol–adenosine hybrids as inhibitors of 17β-hydroxysteroid dehydrogenase type 1
  作者：Marie Bérubé、Donald Poirier

  DOI：10.1139/v09-083

  日期：2009.8

  and the cofactor-binding sites of 17β-hydroxysteroid dehydrogenase type 1 (17β-HSD1). These analogues of potent E2–adenosine hybrid inhibitor EM-1745, where the adenosine moiety was replaced by a more stable benzene derivative, were synthesized from estrone using alkene cross-metathesis and Sonogashira coupling reactions as key steps. In vitro biological evaluation of these steroid derivatives revealed

  一系列雌二醇 (E2) 衍生物被设计为与 17β-羟基类固醇脱氢酶 1 (17β-HSD1) 的底物和辅因子结合位点相互作用。这些有效的 E2-腺苷杂化抑制剂 EM-1745 的类似物，其中腺苷部分被更稳定的苯衍生物取代，是使用烯烃交叉复分解和 Sonogashira 偶联反应作为关键步骤从雌酮合成的。这些类固醇衍生物的体外生物学评估表明，在 E2 的 16β 位和带有羧酸基团的腺苷模拟物之间的 13 个亚甲基间隔物对 17β-HSD1 的抑制作用最好。
• Selective Anion Binding by a Macrocycle with Convergent Hydrogen Bonding Functionality
  作者：Kihang Choi、Andrew D. Hamilton

  DOI：10.1021/ja005772+

  日期：2001.3.1