1-(3-iodo-4-hydroxy-phenyl)-1-phenyl-methanone | 170744-87-3

• 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: 1-(3-iodo-4-hydroxy-phenyl)-1-phenyl-methanone
• 英文别名: 4-hydroxy-3-iodo-benzophenone；4-Hydroxy-3-jod-benzophenon；[125I]-3-iodo-4-hydroxybenzophenone；(4-Hydroxy-3-iodophenyl)(phenyl)methanone；(4-hydroxy-3-iodophenyl)-phenylmethanone
• CAS: 170744-87-3
• 化学式: C₁₃H₉IO₂
• 分子量: 324.118
• InChiKey: YKAHHNPIXNXHLX-UHFFFAOYSA-N

物化性质

• 熔点：
  184°C
• 沸点：
  388.5±32.0 °C(Predicted)
• 密度：
  1.723±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• 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：

  1-(3-iodo-4-hydroxy-phenyl)-1-phenyl-methanone 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium fluoride 、 copper(l) iodide 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 6.0h， 生成 p-benzoyl-o-ethynylphenol
  参考文献：
  名称：

  Palladium-Catalyzed Reaction of o-Ethynylphenols, o-((Trimethylsilyl)ethynyl)phenyl Acetates, and o-Alkynylphenols with Unsaturated Triflates or Halides:  A Route to 2-Substituted-, 2,3-Disubstituted-, and 2-Substituted-3-acylbenzo[b]furans

  摘要：

  The reaction of o-ethynylphenols 3 with a wide variety of unsaturated halides or triflates 6 in the presence of Pd(OAc)(2)(PPh(3))(2), CuI, and Et(3)N (procedure A) gives 2-vinyl- and 2-arylbenzo[b]furans 7, in good to high yield, through a palladium-catalyzed coupling followed by an in situ cyclization step. Small amounts of 2,3-disubstituted-benzo[b]furans 8 are usually isolated as side products. In some cases, however, compounds 8 are generated in significant yield or even as the main products. The formation of 8 can be prevented by employing alternative procedures (B and C) that use o-((trimethylsilyl)ethynyl)phenyl acetates 5 as starting building blocks. Procedure B is based on the palladium-catalyzed reaction of 5 with 6 in the presence of Pd(PPh(3))(4), Et(3)N, and n-Bu(4)NF, followed by the hydrolysis of the resultant coupling derivative 12 under basic conditions. Procedure C affords 7 through an in situ coupling/cyclization of 5 with 6 in the presence of Pd(PPh(3))(4) and KOBu(t). The utilization of o-alkynylphenols 9 as the starting alkynes in the palladium-catalyzed reaction with 6 leads to the formation of 2,3-disubstituted-benzo[b]furans 13 through an annulation process promoted by sigma-vinyl- and sigma-arylpalladium complexes generated in situ. The best results in this case are obtained by using KOAc and Pd(PPh(3))(4). In the presence of KOAc and Pd(PPh(3))(4), and under an atmosphere of carbon monoxide, the reaction of o-alkynylphenols with 6 provides 2-vinyl- and 2-aryl-3-acylbenzo[b]furans 14.

  DOI：

  10.1021/jo961051a
• 作为产物：
  描述：

  4-羟基-二苯甲酮 在 碘 、 potassium iodide 作用下， 以 ammonium hydroxide 、 水 为溶剂， 以37%的产率得到1-(3-iodo-4-hydroxy-phenyl)-1-phenyl-methanone
  参考文献：
  名称：

  碘代芳烃的高度化学选择性氢解。

  摘要：

  分子氢和Pd / C的催化加氢脱卤反应已被重新考虑。结果表明，随着电负性I

  DOI：

  10.1021/jo0109669

文献信息

• Efficient and sustainable laccase-catalyzed iodination of<i>p</i>-substituted phenols using KI as iodine source and aerial O₂as oxidant
  作者：Mark Sdahl、Jürgen Conrad、Christina Braunberger、Uwe Beifuss

  DOI：10.1039/c9ra02541c

  日期：——

  The laccase-catalyzed iodination of p-hydroxyarylcarbonyl- and p-hydroxyarylcarboxylic acid derivatives using KI as iodine source and aerial oxygen as the oxidant delivers the corresponding iodophenols in a highly efficient and sustainable manner with yields up to 93% on a preparative scale under mild reaction conditions.

  使用 KI 作为碘源和空气中的氧气作为氧化剂，漆酶催化对羟基芳基羰基和对羟基芳基羧酸衍生物的碘化反应，以高效且可持续的方式生成相应的碘酚，在温和条件下制备规模的收率高达 93%反应条件。
• Carboxylic acid derivatives as IP antagonists
  申请人：——

  公开号：US20010056100A1

  公开（公告）日：2001-12-27

  This invention relates to compounds which are generally IP receptor antagonists and which are represented by Formula I: 1 wherein: R 1 , R 2 , and R 3 are each independently in each occurrence aryl or heteroaryl; R 4 is —COOH or tetrazolyl; A, B, m, n, and r are as defined in the specification; or individual isomers, racemic or non-racemic mixtures of isomers, or pharmaceutically acceptable salts or solvates thereof. The invention further relates to pharmaceutical compositions containing such compounds, methods for their use as therapeutic agents, and processes for their preparation.

  这项发明涉及一类通常为IP受体拮抗剂的化合物，其由以下式I表示： 其中： R1、R2和R3在每次出现时各自独立地为芳基或杂环芳基； R4为—COOH或四唑基； A、B、m、n和r如规范中定义； 或其各个异构体、外消旋或非外消旋异构体混合物，或其药用可接受盐或溶剂合物。该发明还涉及含有这种化合物的药物组合物，以及将其用作治疗剂的方法和其制备方法。
• Palladium-Catalyzed Selective Carbonylation of Vinyl Triflates in the Presence of 2-Iodophenols: A New Route to 3-Spiro-Fused Benzofuran-2(3H)-ones
  作者：Roberto Anacardio、Antonio Arcadi、Gaetano D’Anniballe、Fabio Marinelli

  DOI：10.1055/s-1995-3991

  日期：1995.7

  A convenient synthesis of 3-spiro-fused benzofuran-2(3H)-ones via palladium-catalyzed chemoselective carbonylation of vinyl triflates in the presence of o-iodophenols, followed by regioselective intramolecular Heck reaction, is described.

  介绍了在邻碘苯酚存在下，通过钯催化乙烯基三甲酸酯的化学选择性羰基化，然后进行区域选择性分子内 Heck 反应，方便地合成 3-螺融合苯并呋喃-2(3H)-酮的方法。
• [EN] CARBOXYLIC ACID DERIVATIVES AS IP ANTAGONISTS<br/>[FR] DERIVES D'ACIDE CARBOXYLIQUE UTILISES COMME DES ANTAGONISTES D'IP
  申请人：HOFFMANN LA ROCHE

  公开号：WO2001068591A1

  公开（公告）日：2001-09-20

  This invention relates to compounds which are generally IP receptor antagonists and which are represented by Formula (I) wherein R?1, R2, and R3¿ are each independently in each occurrence aryl or heteroaryl, R4 is -COOH or tetrazolyl, A, B, m, n, and r are as defined in the specification; or individual isomers, racemic or non-racemic mixtures of isomers, or pharmaceutically acceptable salts or solvates thereof. The invention further relates to pharmaceutical compositions containing such compounds, processes for their preparation and their use as therapeutic agents.

  本发明涉及一类化合物，通常为IP受体拮抗剂，其由式（I）表示，其中R1、R2和R3在每次出现时均独立地为芳基或杂环芳基，R4为-COOH或四唑基，A、B、m、n和r如规范中所定义；或其各个异构体，混合物，或其药学上可接受的盐或溶剂。本发明还涉及含有这种化合物的药物组合物，其制备方法以及作为治疗剂的用途。
• S1P receptor modulating compounds and use thereof
  申请人：Burli Roland

  公开号：US20080027036A1

  公开（公告）日：2008-01-31

  The present invention relates to compounds of the general formula (I) that have activity as S1P receptor modulating agents and the use of such compounds to treat diseases associated with inappropriate S1P receptor activity. The compounds may be used as immunomodulators, e.g., for treating or preventing diseases such as autoimmune and related immune disorders including systemic lupus erythematosus, inflammatory bowel diseases such as Crohn's disease and ulcerative colitis, type I diabetes, uveitis, psoriasis, myasthenia gravis, rheumatoid arthritis, non-glomerular nephrosis, hepatitis, Behçet's disease, glomerulonephritis, chronic thrombocytopenic purpura, hemolytic anemia, hepatitis and Wegner's granuloma; and for treating other conditions.

  本发明涉及一般式（I）的化合物，其具有作为S1P受体调节剂的活性，以及使用这种化合物来治疗与不适当的S1P受体活性相关的疾病。这些化合物可以用作免疫调节剂，例如，用于治疗或预防自身免疫和相关免疫紊乱疾病，包括系统性红斑狼疮、炎症性肠病，如克隆病和溃疡性结肠炎、1型糖尿病、葡萄膜炎、牛皮癣、重症肌无力、类风湿性关节炎、非肾小球性肾病、肝炎、Behçet病、肾小球肾炎、慢性血小板减少性紫癜、溶血性贫血、肝炎和Wegner肉芽肿；以及用于治疗其他疾病。