4-氟-3-碘苯甲酸甲酯 | 1121586-29-5

• 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: 4-氟-3-碘苯甲酸甲酯
• 中文别名: 3-碘-4-氟苯甲酸甲酯
• 英文名称: methyl 4-fluoro-3-iodobenzoate
• CAS: 1121586-29-5
• 化学式: C₈H₆FIO₂
• 分子量: 280.037
• InChiKey: VVVNAJAWYUURAO-UHFFFAOYSA-N

物化性质

• 熔点：
  42-43℃
• 沸点：
  288℃
• 密度：
  1.823
• 闪点：
  128℃

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  4-氟-3-碘苯甲酸甲酯 在 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 sodium hydride 、 potassium carbonate 、 caesium carbonate 、 1-丙基磷酸酐 、 三苯基膦 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 20.0~120.0 ℃ 、500.01 kPa 条件下， 反应 31.75h， 生成 methyl 2-(9-ethyl-8-methyl-9H-carbazol-3-yl)-1-(2-methoxyethyl)-4-methyl-1H-benzimidazole-5-carboxylate
  参考文献：
  名称：

  Identification of a Benzimidazolecarboxylic Acid Derivative (BAY 1316957) as a Potent and Selective Human Prostaglandin E2 Receptor Subtype 4 (hEP4-R) Antagonist for the Treatment of Endometriosis

  摘要：

  The presence and growth of endometrial tissue outside the uterine cavity in endometriosis patients are primarily driven by hormone-dependent and inflammatory processes-the latter being frequently associated with severe, acute, and chronic pelvic pain. The EP4 subtype of prostaglandin E2 (PGE2) receptors (EP4-R) is a particularly promising antiinflammatory and antinociceptive target as both this receptor subtype and the pathways forming PGE2 are highly expressed in endometriotic lesions. High-throughput screening resulted in the identification of benzimidazole derivatives as novel hEP4-R antagonists. Careful structure-activity relationship investigation guided by rational design identified a methyl substitution adjacent to the carboxylic acid as an appropriate means to accomplish favorable pharmacokinetic properties by reduction of glucuronidation. Further optimization led to the identification of benzimidazolecarboxylic acid BAY 1316957, a highly potent, specific, and selective hEP4-R antagonist with excellent drug metabolism and pharmacokinetics properties. Notably, treatment with BAY 1316957 can be expected to lead to prominent and rapid pain relief and significant improvement of the patient's quality of life.

  DOI：

  10.1021/acs.jmedchem.8b01862
• 作为产物：
  描述：

  3-氨基-4-氟苯甲酸 在 盐酸 、 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 、 sodium nitrite 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 25.0h， 生成 4-氟-3-碘苯甲酸甲酯
  参考文献：
  名称：

  Development and Preliminary Evaluation of TFIB, a New Bimodal Prosthetic Group for Bioactive Molecule Labeling

  摘要：

  The new readily available prosthetic group, tetrafluorophenyl 4-fluoro-3-iodobenzoate (TFIB), designed for both molecular imaging and targeted radionuclide therapy purposes was radiolabeled either with fluorine or iodine radionuclides with excellent radiochemical yields and purities. These radiolabeled tags were conjugated to N,N-diethylethylenediamine to give melanin-targeting radiotracers [ (125) I]9 and [ (18) F]9, which were successfully evaluated by PET and gamma scintigraphic imaging in B16F0 pigmented melanoma-bearing C57BL/6J mice. Then, radiolabeled [ (125) I]/[ (18) F]TFIB was used to tag tumor-targeting peptides (i.e., PEG3[c(RGDyK)]2 and NDP-MSH targeting αvβ3 integrin and MC1R receptors, respectively) in mild conditions and with good radiochemical yields (47-83% d.c.) and purities (>99%). The resulting radiolabeled peptides were assessed both in vitro and by PET imaging in animal models.

  DOI：

  10.1021/ml500423v

文献信息

• [EN] HETEROCYCLIC MODULATORS OF LIPID SYNTHESIS AND COMBINATIONS THEREOF<br/>[FR] MODULATEURS HÉTÉROCYCLIQUES DE LA SYNTHÈSE DES LIPIDES ET COMBINAISONS EN CONTENANT
  申请人：3 V BIOSCIENCES INC

  公开号：WO2015095767A1

  公开（公告）日：2015-06-25

  Heterocyclic modulators of lipid synthesis are provided as well as pharmaceutically acceptable salts thereof; pharmaceutical compositions comprising such compounds; and methods of treating conditions characterized by disregulation of a fatty acid synthase pathway by the administration of such compounds and combinations of such compounds and other therapeutic agents.

  提供了杂环调节剂脂质合成以及其药用盐；包括这些化合物的药物组合物；以及通过给予这些化合物和其他治疗剂的组合来治疗脂肪酸合酶途径失调症状的方法。
• [EN] HETEROCYCLIC MODULATORS OF LIPID SYNTHESIS<br/>[FR] MODULATEURS HÉTÉROCYCLIQUES DE LA SYNTHÈSE DES LIPIDES
  申请人：3 V BIOSCIENCES INC

  公开号：WO2014008197A1

  公开（公告）日：2014-01-09

  Heterocyclic modulators of lipid synthesis are provided as well as pharmaceutically acceptable salts thereof; pharmaceutical compositions comprising such compounds; and methods of treating conditions characterized by disregulation of a fatty acid synthase pathway by the administration of such compounds.

  提供了异环调节脂质合成的调节剂及其药用盐；包括这些化合物的药物组合物；以及通过给予这些化合物来治疗由于脂肪酸合酶途径失调而表现出的疾病的方法。
• Ligand‐Enabled β‐Methylene C(sp ³ )−H Arylation of Masked Aliphatic Alcohols
  作者：Guoqin Xia、Zhe Zhuang、Luo‐Yan Liu、Stuart L. Schreiber、Bruno Melillo、Jin‐Quan Yu

  DOI：10.1002/anie.202000632

  日期：2020.5.11

  salicylic-aldehyde-derived L,X-type directing group with an electron-deficient 2-pyridone ligand to enable the β-methylene C(sp3 )-H arylation of aliphatic alcohols, which has not been possible previously. Notably, this protocol is compatible with heterocycles embedded in both alcohol substrates and aryl coupling partners. A site- and stereo-specific annulation of dihydrocholesterol and the synthesis of a key

  尽管有最新进展，但是反应性和位点选择性仍然是C（sp3）-H键官能化方法实际应用的重大障碍。在这里，我们描述了一个系统，该系统将水杨醛衍生的L，X型导向基团与缺电子的2-吡啶酮配体结合在一起，以使脂肪族醇的β-亚甲基C（sp3）-H芳基化以前有可能。值得注意的是，该方案与嵌入在醇底物和芳基偶联伙伴中的杂环兼容。二氢胆固醇的位点和立体特异性环合以及恩格列酮的关键中间体的合成说明了该方法的实用性。
• [EN] DIHYDROPYRIMIDINE COMPOUNDS AND USES THEREOF IN MEDICINE<br/>[FR] COMPOSÉS DIHYDROPYRIMIDINE ET UTILISATIONS DE CEUX-CI EN MÉDECINE
  申请人：SUNSHINE LAKE PHARMA CO LTD

  公开号：WO2019001396A1

  公开（公告）日：2019-01-03

  Provided herein are a dihydropyrimidine compound and a pharmaceutical application thereof, especially the application used for treating and preventing HBV diseases. Specifically, provided herein is a compound having Formula (I) or (Ia), or an enantiomer, a diastereoisomer, a tautomer, a hydrate, a solvate, or a pharmaceutically acceptable salt thereof, wherein the variables of the formulas are as defined in the specification. Also provided herein is use of the compound having Formula (I) or (Ia), or an enantiomer, a diastereoisomer, a tautomer, a hydrate, a solvate, or a pharmaceutically acceptable salt thereof as a medicine, especially for treating and preventing HBV diseases.

  本文提供了一种二氢嘧啶化合物及其药物应用，特别是用于治疗和预防HBV疾病的应用。具体来说，本文提供了具有化学式（I）或（Ia）的化合物，或其对映体、异构体、互变异构体、水合物、溶剂合物或其药用可接受的盐，其中化学式的变量如规范中定义。本文还提供了将具有化学式（I）或（Ia）的化合物，或其对映体、异构体、互变异构体、水合物、溶剂合物或其药用可接受的盐用作药物的用途，特别是用于治疗和预防HBV疾病。
• High-Triplet-Energy Dendrons: Enhancing the Luminescence of Deep Blue Phosphorescent Iridium(III) Complexes
  作者：Shih-Chun Lo、Ruth E. Harding、Christopher P. Shipley、Stuart G. Stevenson、Paul L. Burn、Ifor D. W. Samuel

  DOI：10.1021/ja903157e

  日期：2009.11.25

  coordinates of (0.16, 0.16). The results demonstrate that dendronization of simple chromophores can enhance their properties. Single layer neat dendrimer organic light-emitting diodes (OLEDs) had an external quantum efficiency (EQE) of 0.4% at 100 cd/m(2). Bilayer devices with an electron transport layer gave improved EQEs of up to 3.9%. Time-resolved luminescence measurements suggest that quenching of triplets

  具有高发光效率的可溶液加工的蓝色磷光发光体非常适合大面积显示器和照明应用。该报告表明，当 fac-tris[1-methyl-5-(4-fluorophenyl)-3-n-propyl-1H-[1,2,4]triazolyl]iridium(III) 复合核被刚性高-三重态能量树突，物理和光物理特性都可以优化。高三重态和刚性树枝由扭曲的联苯树枝组成，扭曲是由于使用四取代的支化苯环而引起的。蓝色磷光树枝状聚合物是使用会聚方法合成的，并且被发现是可溶液加工的，并且具有 148 摄氏度的高玻璃化转变温度。 该树枝状聚合物具有 94% 的超高溶液光致发光量子产率 (PLQY)，是简单母核复合体 (27%) 的三倍多。还发现刚性和高三线态能量树突控制导致固态发光猝灭的分子间相互作用，并且发现薄膜 PLQY 为 60%，其发射具有 Commission Internationale de l'Eclairage