3-(4-bromophenyl)-1-phenylbutan-1-one | 1611492-49-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-(4-bromophenyl)-1-phenylbutan-1-one
• CAS: 1611492-49-9
• 化学式: C₁₆H₁₅BrO
• 分子量: 303.198
• InChiKey: XZUCCKSIGNXQKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  在 4-hydroxy-2,6-di(naphthalen-2-yl)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine 4-oxide 、 频那醇硼烷 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 生成 3-(4-bromophenyl)-1-phenylbutan-1-one
  参考文献：
  名称：

  使用BINOL衍生的硼磷酸盐催化反查尔酮衍生物的不对称转移氢化反应。

  摘要：

  在这项工作中，已经研究了手性磷酸催化反式查耳酮的不对称还原。利用硼烷作为氢化物来源，实现了反式查尔酮衍生物的碳-碳双键的BINOL衍生的硼磷酸盐催化的不对称转移氢化。该方法提供了在温和条件下以高收率和高对映选择性获得手性二氢氢醌衍生物的简便方法。

  DOI：

  10.1021/acs.orglett.0c02042

文献信息

• Catalytic Carbocation Generation Enabled by the Mesolytic Cleavage of Alkoxyamine Radical Cations
  作者：Qilei Zhu、Emily C. Gentry、Robert R. Knowles

  DOI：10.1002/anie.201604619

  日期：2016.8.16

  weak C−O bond. Spontaneous scission results in the formation of the stable nitroxyl radical TEMPO. as well as a reactive carbocation intermediate that can be intercepted by a wide range of nucleophiles. Notably, this process occurs under neutral conditions and at comparatively mild potentials, enabling catalytic cation generation in the presence of both acid sensitive and easily oxidized nucleophilic

  描述了一种新的催化方法，该方法通过烷氧基胺自由基阳离子的介观裂解来获得碳正离子中间体。在此过程中，激发态氧化剂与TEMPO衍生的烷氧基胺底物之间的电子转移会产生带有非常弱的C-O键的自由基阳离子。自发断裂导致形成稳定的硝基自由基TEMPO 。以及可被多种亲核试剂截获的反应性碳正离子中间体。值得注意的是，该过程在中性条件下和相对温和的电势下发生，从而在酸敏感和易氧化的亲核分子同时存在的情况下能够产生催化阳离子。
• Alcohols as electrophiles: iron-catalyzed Ritter reaction and alcohol addition to alkynes
  作者：Latisha R. Jefferies、Silas P. Cook

  DOI：10.1016/j.tet.2014.03.072

  日期：2014.7

  iron-based catalytic system allows for a straightforward method for the synthesis of primary, secondary, and tertiary amides. The system also allows the addition of benzyl alcohols across phenylacetylene to produce substituted phenyl ketones. This transformation improves and expands the substrate scope beyond that previously reported and proceeds under mild reaction conditions, tolerating air and moisture

  一个简单的铁基催化体系为合成伯，仲和叔酰胺提供了一种简单的方法。该系统还允许在苯乙炔上添加苄醇以产生取代的苯酮。这种转变改善并扩大了底物的范围，使其超出了先前报道的范围，并在温和的反应条件下进行，可耐受空气和水分。
• Synthesis of Chiral β,β-Disubstituted Ketones via CuH-Catalyzed Coupling of Aryl Alkenes and 3-Aryl-2<i>H</i>-azirines
  作者：Fang Xie、Shijie Dong、Yajun Sun、Wenxing Liu、Xiaodan Liu、Lu Liu、Qin Zhao、Jiangli Wang

  DOI：10.1021/acs.orglett.2c03311

  日期：2022.11.11

  A CuH-catalyzed coupling of aryl alkenes with 3-aryl-2H-azirines has been developed to synthesize optically active β,β-disubstituted ketones. We propose that this protocol occurs through a sequence in which a chiral alkylcopper complex regioselectively attacks the N–C2 bonds of azirines to generate chiral β-aryl imines, which additionally afford ketones upon hydrolysis. This method provides a novel

  已经开发了芳基烯烃与 3-aryl-2 H-氮杂环丙烷的 CuH 催化偶联，以合成具有光学活性的 β,β-二取代酮。我们建议该方案通过一个序列发生，在该序列中，手性烷基铜络合物区域选择性地攻击氮杂环丙烷的 N-C2 键以生成手性 β-芳基亚胺，后者在水解时另外提供酮。该方法为在温和条件下以高对映选择性合成手性 β,β-二取代酮提供了一种新的互补方法。
• Synthesis of Substituted Aryl Ketones by Addition of Alcohols to Alkynes Using Amberlyst-15/Ionic Liquid as a Recyclable Catalytic System
  作者：Bhalchandra Bhanage、Kishor Wagh

  DOI：10.1055/s-0034-1380142

  日期：——

  A highly efficient protocol for the synthesis of substituted aryl ketones by using Amberlyst-15 immobilized in [Bmim][PF6] ionic liquid has been firstly developed. The present protocol works under metal-free, solvent-free, mild reaction conditions with 100% atom efficiency. The various aryl ketones were obtained in good to excellent yields. The developed catalytic system was recycled efficiently up to five cycles without significant loss in catalytic activity.
• Cyclopentanone as a Cation-Stabilizing Electron-Pair Donor in the Calcium-Catalyzed Intermolecular Carbohydroxylation of Alkynes
  作者：Tobias Stopka、Meike Niggemann

  DOI：10.1021/acs.orglett.5b00312

  日期：2015.3.20

  Although they have been used as reactivity-controlling additives in cationic polymerizations for decades, Lewis basic electron pair donor (ED) compounds were never used for the stabilization of cationic intermediates in transformations of small molecules. As such an ED, cyclopentanone proved highly efficient for the stabilization of allyl and vinyl cations in combination with our calcium-based catalyst system. Therefore, the first general transition-metal-free intermolecular carbohydroxylation of alkynes with allyl and propargyl alcohols was realized.