1-phenyl-2-(m-tolyl)-1-propanone | 1315258-38-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1-phenyl-2-(m-tolyl)-1-propanone
• 英文别名: 1-phenyl-2-(m-tolyl)propan-1-one；2-(3-methylphenyl)-1-phenylpropan-1-one
• CAS: 1315258-38-8
• 化学式: C₁₆H₁₆O
• 分子量: 224.302
• InChiKey: FONVDCDJUVECGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-phenyl-2-(m-tolyl)-1-propanone 在 C₄₆H₅₂N₄O₂⁽²⁺⁾*2Br^(1-) 、 氧气 、 1,2-双(二苯基膦)乙烷 、 sodium hydroxide 作用下， 以 水 、 苯 为溶剂， 反应 24.0h， 以72%的产率得到
  参考文献：
  名称：

  Phase-Transfer-Catalyzed Enantioselective α-Hydroxylation of Acyclic and Cyclic Ketones with Oxygen

  摘要：

  An efficient and enantioselective alpha-hydroxylation of acyclic as well as cyclic ketones using molecular oxygen has been developed. This simple catalytic procedure uses a readily available phase transfer catalyst and produces a wide range of valuable tertiary a-hydroxy ketones in good to excellent enantiopurity.

  DOI：

  10.1021/acscatal.5b00583
• 作为产物：
  描述：

  3-氯甲苯 、 苯丙酮 在 C₄₀H₄₄ClN₃Pd 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以89%的产率得到1-phenyl-2-(m-tolyl)-1-propanone
  参考文献：
  名称：

  N-杂环卡宾-四环配合物：合成，表征及其在芳基氯化物的酮的CN偶联和α-芳基化中的应用

  摘要：

  在温和条件下，通过一锅法成功地获得了N-杂环卡宾-四环复合物3。通过X射线单晶衍射明确证实了3a的结构，即使在极低的催化剂负载量（0.01摩尔％）下，它仍是Buchwald-Hartwig胺化和酮的α-芳基化反应中的活性催化剂。

  DOI：

  10.1016/j.tet.2018.07.052

文献信息

• N-Heterocyclic carbene-palladacyclic complexes: synthesis, characterization and their applications in the C-N coupling and α-arylation of ketones using aryl chlorides
  作者：Feng Liu、Yuan-Yuan Hu、Di Li、Quan Zhou、Jian-Mei Lu

  DOI：10.1016/j.tet.2018.07.052

  日期：2018.9

  a one-pot procedure under mild conditions. The structure of 3a was unambiguously confirmed by X-ray single crystal diffraction and it was an active catalyst in the Buchwald-Hartwig amination and α-arylation of ketones even at very low catalyst loadings (0.01 mol%).

  在温和条件下，通过一锅法成功地获得了N-杂环卡宾-四环复合物3。通过X射线单晶衍射明确证实了3a的结构，即使在极低的催化剂负载量（0.01摩尔％）下，它仍是Buchwald-Hartwig胺化和酮的α-芳基化反应中的活性催化剂。
• Allyl complexes for use in coupling reactions
  申请人：Colacot Thomas John

  公开号：US10167305B2

  公开（公告）日：2019-01-01

  A complex of formula (1), wherein, M is palladium or nickel, R1 and R2 are independently organic groups having 1-20 carbon atoms, or R1 and R2 are linked to form a ring structure with the phosphorus atom, R3 is selected from the group consisting of substituted and unsubstituted aryl, substituted and unsubstituted heteroaryl, and substituted and unsubstituted metallocenyl, R4 is an organic group having 1-20 carbon atoms, n is 0, 1, 2, 3, 4 or 5, X is an anionic ligand. A process for the preparation of the complex, and its use in carbon-carbon or carbon-nitrogen coupling reactions is also provided.

  一个公式复合物（1），其中，M为钯或镍，R1和R2分别是具有1-20个碳原子的有机基团，或者R1和R2连接形成与磷原子的环结构，R3从取代和未取代芳基、取代和未取代杂环基和取代和未取代金属茂基组成的群体中选择，R4是具有1-20个碳原子的有机基团，n为0、1、2、3、4或5，X为阴离子配体。还提供了一种制备该复合物的方法，以及其在碳-碳或碳-氮偶联反应中的用途。
• N-Heterocyclic Carbene-Palladium(II)-1-Methylimidazole Complex Catalyzed α-Arylation of Ketones with Aryl Chlorides
  作者：Li-Xiong Shao、Zheng-Kang Xiao

  DOI：10.1055/s-0031-1289698

  日期：2012.3

  An easily available NHC-Pd(II)-Im (NHC = N-heterocyclic carbene, Im = 1-methylimidazole) complex was found to be an efficient catalyst for the α-arylation reaction between ketones and aryl chlorides. Under the optimal conditions, all reactions proceeded smoothly to give the desired products in good to high yields within hours.

  一种易得的 NHC-Pd(II)-Im 复合物（NHC = N-杂环碳氢化物，Im = 甲基咪唑）被发现是一种高效的催化剂，适用于酮和芳香氯之间的 α-芳基化反应。在最佳条件下，所有反应均顺利进行，所需的产物在数小时内以良好到高的产率得到。
• DIALKYL(2-ALKOXY-6-AMINOPHENYL)PHOSPHINE, THE PREPARATION METHOD AND USE THEREOF
  申请人：Ma Shengming

  公开号：US20140309422A1

  公开（公告）日：2014-10-16

  The present invention relates to the compound of dialkyl(2-alkoxy-6-aminophenyl)phosphine and the preparation method thereof and the application in the palladium catalyzed coupling reactions of aryl chloride and ketone. The dialkyl(2-alkoxy-6-aminophenyl)phosphine of the present invention could coordinate with the palladium catalyst to highly selectively activate the inert carbon-chlorine bond, and to catalyze direct arylation reaction in the α-position of ketones to produce corresponding coupling compounds. The preparation method of the present invention is a simple one-step method which produces the air-stable dialkyl(2-alkoxy-6-aminophenyl)phosphine. Compared with the synthetic routes of ligands to be used in the activation of carbon-chlorine bonds in the prior arts, the preparation method of the present invention has the advantages of short route and easy operation.

  本发明涉及二烷基（2-烷氧基-6-氨基苯基）膦化合物及其制备方法，以及在钯催化芳基氯化物和酮的偶联反应中的应用。本发明的二烷基（2-烷氧基-6-氨基苯基）膦化合物能够与钯催化剂配位，高度选择性地活化惰性碳-氯键，并催化酮的α位直接芳基化反应，生成相应的偶联化合物。本发明的制备方法是一种简单的一步法，可制备出稳定于空气中的二烷基（2-烷氧基-6-氨基苯基）膦化合物。与先前用于活化碳-氯键的配体的合成路线相比，本发明的制备方法具有路线短、操作简便的优点。
• A highly active and selective palladium pincer catalyst for the formation of α-aryl ketones via cross-coupling
  作者：Alejandro Bugarin、Brian T. Connell

  DOI：10.1039/c1cc12071a

  日期：——

  Several air and moisture stable Pd(II) pincer complexes were synthesized via oxidative addition of Pd(0) to novel PheBox pincer ligand precursors. Low loadings (1 mol%) of the Pd complex [t-BuPhebox-Me2]PdBr are capable of efficiently promoting the selective α-monoarylation of a variety of ketones with numerous aryl bromides in only 1 h at 70 °C with 82–99% yields.

  几种空气和湿气稳定的Pd(II)夹心配合物是通过Pd(0)与新型PheBox夹心配体前体的氧化加成合成的。低含量（1 mol%）的Pd配合物[t-BuPhebox-Me2]PdBr能够在70°C下仅用1小时高效促进多种酮与众多芳基溴的选择性α-单芳基化，产率为82%–99%。