(5-bromo-2-methoxyphenyl)(phenyl)methanone

• 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: (5-bromo-2-methoxyphenyl)(phenyl)methanone
• 英文别名: (5-bromo-2-methoxyphenyl)-phenylmethanone
• 化学式: C₁₄H₁₁BrO₂
• mdl: MFCD11105727
• 分子量: 291.144
• InChiKey: ADGOJIXMUSHYQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 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：

  (5-bromo-2-methoxyphenyl)(phenyl)methanone 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 5-溴-2-羟基二苯甲酮
  参考文献：
  名称：

  Discovery and SAR studies of novel GlyT1 inhibitors

  摘要：

  Inhibition of the glycine transporter GlyTl is a potential strategy for the treatment of schizophrenia A novel series of GlyTl inhibitors and their structure-activity relationships (SAR) are described. Members of this series are highly potent and selective transport inhibitors which are shown to elevate glycine levels in cerebrospinal fluid. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.06.074
• 作为产物：
  描述：

  sodium benzoate 在 bis(η3-allyl-μ-chloropalladium(II)) 、 一氧化碳 、 碘 、 三苯基膦 作用下， 以 1,2-二氯乙烷 为溶剂， 20.0~60.0 ℃ 、405.33 kPa 条件下， 反应 40.0h， 生成 (5-bromo-2-methoxyphenyl)(phenyl)methanone
  参考文献：
  名称：

  一氧化碳脱羧：将羧酸直接转化为强效三氟甲磺酸亲电子试剂

  摘要：

  我们报告了一种将羧酸转化为强效三氟甲磺酸亲电子试剂的新策略。该反应涉及在AgOTf存在下用I 2氧化羧酸的羰基化反应，并假定该反应是通过与CO反应形成三氟甲磺酸酯的酰基次碘酸盐进行的。将这种化学反应与随后的芳烃捕集相结合，可提供一种温和的室温方法，无需使用腐蚀性和反应性的路易斯或布朗斯台德酸添加剂即可直接从广泛存在的羧酸中生成酮，而从易于获得，稳定且功能强大的化合物中生成酮组兼容。

  DOI：

  10.1002/anie.201814660

文献信息

• Focused <i>ortho</i> ‐Lithiation and Functionalization of <i>p</i> ‐Bromo‐ and <i>p</i> ‐Iodoanisole
  作者：D. W. Slocum、John A. Jennings、Thomas K. Reinscheld、Paul E. Whitley

  DOI：10.1002/ejoc.201800616

  日期：2018.8.31

  By use of the strategy of ortho‐lithiation, p‐bromoanisole and p‐iodoanisole were ortho‐metalated using ortho‐lithiodimethylbenzylamine as the metalating agent. No halogen exchange was noted during these same conditions. These studies add to the emerging evidence of a hitherto unidentified acidifying effect on the proton(s) ortho‐ to a directing metalation group by both a p‐iodo and a p‐bromo substituent

  通过邻位锂化的策略，使用邻硫代二甲基二甲基苄胺作为金属化剂对对溴茴香醚和对碘苯甲醚进行邻位金属化。在这些相同条件下未观察到卤素交换。这些研究增加对质子（S）迄今不明酸化作用的新证据邻-由既是一个导演金属化组p碘和p溴取代。
• Cobalt-Catalyzed Enantioselective Hydrogenation of Diaryl Ketones with Ferrocene-Based Secondary Phosphine Oxide Ligands
  作者：Liyao Zeng、Menglong Zhao、Bijin Lin、Jingyuan Song、James H. R. Tucker、Jialin Wen、Xumu Zhang

  DOI：10.1021/acs.orglett.3c02530

  日期：2023.8.25

  A new class of cobalt catalytic system for asymmetric hydrogenation of ketones was herein reported, involving the development of novel ferrocene-based secondary phosphine oxide ligands. An unusual P–O bidentate coordination pattern with cobalt was confirmed by an X-ray diffraction study. The bichelating tetrahedral cobalt(II) complexes afforded high reactivities (up to 99% yield) and good to excellent

  本文报道了一种用于酮不对称氢化的新型钴催化系统，涉及新型二茂铁基二氧化膦配体的开发。X 射线衍射研究证实了与钴的不寻常的 P-O 二齿配位模式。双螯合四面体钴(II)配合物在各种邻位取代的二芳基酮的AH中具有高反应活性（产率高达99%）和良好至优异的对映选择性（高达92% ee）。此外，二茂铁基钴配合物具有有趣的紫外-可见吸收和电化学性质。
• Catalytic Friedel–Crafts acylation: magnetic nanopowder CuFe2O4 as an efficient and magnetically separable catalyst
  作者：Ramarao Parella、Naveen、Amit Kumar、Srinivasarao Arulananda Babu

  DOI：10.1016/j.tetlet.2013.01.081

  日期：2013.3

  Catalytic regioselective Friedel-Crafts acylation of an array of anisoles/arenes with various acid chlorides using 5-20 mol % of magnetic nanopowder CuFe2O4 is reported. Unlike the conventional Friedel-Crafts reactions, which are catalyzed by moisture sensitive homogeneous catalysts/promoters, the nanopowder CuFe2O4 catalyst is moisture insensitive and the product/ketone-catalyst isolation is easily achieved using the magnetic properties of CuFe2O4. (C) 2013 Elsevier Ltd. All rights reserved.
• Discovery and SAR studies of novel GlyT1 inhibitors
  作者：Magnus W. Walter、Beth J. Hoffman、Kimberly Gordon、Kirk Johnson、Patrick Love、Matthew Jones、Teresa Man、Lee Phebus、Jon K. Reel、Helene C. Rudyk、Harlan Shannon、Kjell Svensson、Hong Yu、Matthew J. Valli、Warren J. Porter

  DOI：10.1016/j.bmcl.2007.06.074

  日期：2007.9

  Inhibition of the glycine transporter GlyTl is a potential strategy for the treatment of schizophrenia A novel series of GlyTl inhibitors and their structure-activity relationships (SAR) are described. Members of this series are highly potent and selective transport inhibitors which are shown to elevate glycine levels in cerebrospinal fluid. (c) 2007 Elsevier Ltd. All rights reserved.
• Decarboxylation with Carbon Monoxide: The Direct Conversion of Carboxylic Acids into Potent Acid Triflate Electrophiles
  作者：R. Garrison Kinney、Bruce A. Arndtsen

  DOI：10.1002/anie.201814660

  日期：2019.4

  carboxylic acids into potent acid triflate electrophiles. The reaction involves oxidative carbonylation of carboxylic acids with I2 in the presence of AgOTf, and is postulated to proceed via acyl hypoiodites that react with CO to form acid triflates. Coupling this chemistry with subsequent trapping with arenes offers a mild, room temperature approach to generate ketones directly from broadly available carboxylic

  我们报告了一种将羧酸转化为强效三氟甲磺酸亲电子试剂的新策略。该反应涉及在AgOTf存在下用I 2氧化羧酸的羰基化反应，并假定该反应是通过与CO反应形成三氟甲磺酸酯的酰基次碘酸盐进行的。将这种化学反应与随后的芳烃捕集相结合，可提供一种温和的室温方法，无需使用腐蚀性和反应性的路易斯或布朗斯台德酸添加剂即可直接从广泛存在的羧酸中生成酮，而从易于获得，稳定且功能强大的化合物中生成酮组兼容。