2-iodo-4'-methoxybenzophenone | 138504-32-2

• 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: 2-iodo-4'-methoxybenzophenone
• 英文别名: (2-iodophenyl)(4-methoxyphenyl)methanone；2-iodophenyl 4-methoxyphenyl ketone；(2-iodophenyl)-(4-methoxyphenyl)methanone
• CAS: 138504-32-2
• 化学式: C₁₄H₁₁IO₂
• mdl: MFCD00767189
• 分子量: 338.145
• InChiKey: KUKQWJIQTBQWEN-UHFFFAOYSA-N

物化性质

• 熔点：
  84-84.5 °C(Solv: acetone (67-64-1); hexane (110-54-3))
• 沸点：
  428.3±30.0 °C(Predicted)
• 密度：
  1.582±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-iodo-4'-methoxybenzophenone 在 aluminum (III) chloride 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以97%的产率得到(4-hydroxyphenyl)(2-iodophenyl)methanone
  参考文献：
  名称：

  Synthesis and biological evaluation of negative allosteric modulators of the Kv11.1(hERG) channel

  摘要：

  We synthesized and evaluated a series of compounds for their allosteric modulation at the K(v)11.1 (hERG) channel. Most compounds were negative allosteric modulators of [H-3]dofetilide binding to the channel, in particular 7f, 7h-j and 7p. Compounds 7f and 7p were the most potent negative allosteric modulators amongst all ligands, significantly increasing the dissociation rate of dofetilide in the radioligand kinetic binding assay, while remarkably reducing the affinities of dofetilide and astemizole in a competitive displacement assay. Additionally, both 7f and 7p displayed peculiar displacement characteristics with Hill coefficients significantly distinct from unity as shown by e.g., dofetilide, further indicative of their allosteric effects on dofetilide binding. Our findings in this investigation yielded several promising negative allosteric modulators for future functional and clinical research with respect to their antiarrhythmic propensities, either alone or in combination with known K(v)11.1 blockers. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.10.032
• 作为产物：
  描述：

  (2-Iodophenyl)-(4-methoxyphenyl)methanol 在 pyridinium chlorochromate 作用下， 生成 2-iodo-4'-methoxybenzophenone
  参考文献：
  名称：

  钯催化的酰基化：茚满的一锅法合成

  摘要：

  从简单的邻碘酮和醛开始，完成了高效的一锅法合成取代的茚满。关键步骤是用[Pd]催化邻碘酮与醛的直接酰化。随后的分子内羟醛缩合得到茚三酮。值得注意的是，获得了各种茚满。明显地，天然产物新木脂素是在一锅中完成的。

  DOI：

  10.1021/acs.joc.6b02453

文献信息

• Efficient and Fast Method for the Preparation of Diaryl Ketones at Room Temperature
  作者：Abdol Hajipour、Raheleh Pourkaveh

  DOI：10.1055/s-0033-1341070

  日期：——

  the aryl ring of the acyl chlorides. Palladium-catalyzed cross-coupling reaction of aryl­boronic acids with acid chlorides at room temperature under phosphine-free conditions affords the corresponding aromatic ketones in excellent yields within short times. This synthetic method overcomes common disadvantages of Friedel–Crafts acylation procedures and is compatible with both electron-donating and electron-withdrawing

  摘要 室温下在无膦条件下，钯催化的芳基硼酸与酰氯的交叉偶联反应可在短时间内以优异的收率得到相应的芳族酮。这种合成方法克服了Friedel-Crafts酰化方法的共同缺点，并且与酰氯芳基环上的给电子和吸电子取代基兼容。 室温下在无膦条件下，钯催化的芳基硼酸与酰氯的交叉偶联反应可在短时间内以优异的收率得到相应的芳族酮。这种合成方法克服了Friedel-Crafts酰化方法的共同缺点，并且与酰氯芳基环上的给电子和吸电子取代基兼容。
• Lewis or Brønsted acid-catalysed reaction of propargylic alcohol-tethered alkylidenecyclopropanes with indoles and pyrroles for the preparation of polycyclic compounds tethered with indole or pyrrole motif
  作者：Hao-Zhao Wei、Liu-Zhu Yu、Min Shi

  DOI：10.1039/c9ob02211b

  日期：——

  derivatives via the Lewis or Brønsted acid catalysed cascade nucleophilic addition, electronic cyclization, ring-opening rearrangement of propargylic alcohol-tethered alkylidenecyclopropanes with indole and pyrrole derivatives. The reaction exhibited a broad substrate scope and good functional group tolerance under metal-free conditions, affording the desired products in moderate to good yields.

  我们开发了一种简便的合成方法，该方法可通过路易斯或布朗斯台德酸催化的级联亲核加成，电子环化，带有炔丙基和吡咯衍生物的炔丙醇系链亚烷基环丙烷的开环重排来访问环戊五烯[ b ]萘衍生物。该反应在无金属的条件下表现出宽泛的底物范围和良好的官能团耐受性，以中等至良好的产率提供了所需的产物。
• Palladium-Catalyzed Acylation Reactions: A One-Pot Diversified Synthesis of Phthalazines, Phthalazinones and Benzoxazinones
  作者：Basuli Suchand、Gedu Satyanarayana

  DOI：10.1002/ejoc.201800159

  日期：2018.5.24

  proceeds through [Pd]‐catalyzed acylation and nucleophilic cyclocondensation with dinucleophilic reagents. This process was based on direct coupling with simple bench‐top aldehydes without the assistance of directing group and without activating the carbonyl group. The process is highly advantageous because it employs simple nitrogen‐based nucleophiles, and non‐toxic and readily accessible aldehydes as the

  提出了一种用于酞嗪、酞嗪酮和苯并恶嗪酮多样化合成的连续单锅策略。该策略通过 [Pd] 催化的酰化和与双亲核试剂的亲核环缩合反应进行。该过程基于与简单的台式醛直接偶联，没有导向基团的帮助，也没有活化羰基。该方法非常有利，因为它使用简单的氮基亲核试剂和无毒且易于获得的醛作为羰基来源。最重要的是，该策略被应用于 PDE-4 抑制剂的一锅合成。
• Preparation and Reactions of Polyfunctional Magnesium Arylcuprates Obtained by an Iodine-Copper Exchange
  作者：Paul Knochel、Xiaoyin Yang

  DOI：10.1055/s-2003-43358

  日期：——

  The preparation of polyfunctional magnesium cuprates of type 1 can be achieved via an iodine-copper exchange reaction using the cyclic magnesium cuprate 3. A range of functional groups like an ester, halide (F, Br), nitrile or even a ketone can be tolerated. The new cuprates can be acylated and allylated in good yields leading to a range of polyfunctional products.

  一类多官能团镁络合物的制备可通过碘铜置换反应利用环状镁络合物3实现。多种官能团，如酯、卤素（氟、溴）、氰基乃至酮，均可被耐受。新型络合物可在良好产率下酰化和烯丙基化，生成一系列多官能团产品。
• Nickel-Catalyzed Cyclization of ortho-Iodoketoximes and ortho-Iodoketimines with Alkynes: Synthesis of Highly Substituted Isoquinolines and Isoquinolinium Salts
  作者：Wei-Chun Shih、Chu-Chun Teng、Kanniyappan Parthasarathy、Chien-Hong Cheng

  DOI：10.1002/asia.201100834

  日期：2012.2.6

  A convenient method for the synthesis of highly substituted isoquinolines and isoquinolinium salts by the nickel‐catalyzed cyclization of ortho‐haloketoximes and ‐ketimines, respectively, with alkynes is described. The reaction of ortho‐haloketoximes and various alkynes in the presence of [Ni(PPh3)2Br2] and zinc powder in a mixture of acetonitrile and tetrahydrofuran at 80 °C for 15 hours gave 1,3

  描述了一种方便的方法，该方法通过炔烃分别通过邻位卤代酮肟和酮缩酮的镍催化环化反应来合成高度取代的异喹啉和异喹啉鎓盐。在[Ni（PPh 3）2 Br 2 ]和锌粉在乙腈和四氢呋喃的混合物中，邻卤代酮肟和各种炔烃在80°C下反应15小时，得到1,3,4-三取代异喹啉产物具有中等至优异的产量和较高的区域选择性。发现相应的异喹啉N-氧化物是环化反应途径中的中间体。相反，邻位反应卤代亚胺和炔烃在相似的催化条件下，在四氢呋喃中于70°C加热2小时，可得到1,2,3,4-四取代的异喹啉鎓盐，收率很好。