3-hydroxy-1-(4-methylphenyl)-2-phenylpropan-1-one | 130906-76-2

• 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: 3-hydroxy-1-(4-methylphenyl)-2-phenylpropan-1-one
• 英文别名: 3-hydroxy-2-phenyl-1-(p-tolyl)propan-1-one；3-Hydroxy-2-phenyl-1-p-tolyl-propanon-(1)；1-p-Tolyl-2-phenyl-3-hydroxy-1-propanon
• CAS: 130906-76-2
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: XFCUOSVSXIORCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 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：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 potassium fluoride 、 双氧水 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以74%的产率得到3-hydroxy-1-(4-methylphenyl)-2-phenylpropan-1-one
  参考文献：
  名称：

  有机光氧化还原催化甲硅烷基硼酸盐的生成

  摘要：

  已经开发了一种由甲硅烷基硼酸盐产生可见光驱动的甲硅烷基自由基的方法。用催化量的温和碱活化甲硅烷基硼酸酯促进了单电子氧化过程形成甲硅烷基自由基。在各种光氧化还原催化剂的存在下，硼酸盐形式的简单单电子转移很容易发生，而氢硅烷没有氢原子转移。将该协议与自由基介导的 N-杂环卡宾催化相结合，通过自由基中继过程与甲硅烷基自由基产生，使烯烃的酰基化成为可能。此外，最近用于合成甲硅烷基硼酸盐的先进方法显着提高了这种甲硅烷基自由基生成过程的效用。

  DOI：

  10.1021/acscatal.2c01964

文献信息

• Organoiodine-induced hydroxylation as well as enantioselective alkoxylation/hydroxylation of allylic alcohols via 1,2- aryl migration
  作者：Liangzhen Hu、Tianyong Gao、Qingfu Deng、Yan Xiong

  DOI：10.1016/j.tet.2021.132334

  日期：2021.8

  A new method for the hydroxylation of allylic alcohols using [hydroxyl(tosyloxy)iodo]benzene (HTIB) as both oxidant and reagent has been developed. Meanwhile, the enantioselective alkyoxylation as well as hydroxylation catalyzed by simple chiral iodine benzene have been developed through the in situ hypervalent iodine synthesis strategy.

  开发了一种使用 [羟基（甲苯磺酰氧基）碘] 苯 (HTIB) 作为氧化剂和试剂对烯丙醇进行羟基化的新方法。同时，通过原位高价碘合成策略开发了对映选择性烷氧基化以及由简单手性碘苯催化的羟基化。
• Metal-Free, One-Pot, Sequential Protocol for Transforming α,β-Epoxy Ketones to β-Hydroxy Ketones and α-Methylene Ketones
  作者：Eietsu Hasegawa、Saki Arai、Eiji Tayama、Hajime Iwamoto

  DOI：10.1021/jo5025249

  日期：2015.2.6

  A new sequential, one-pot protocol for transforming 1,3-disubstituted 2,3-epoxy ketones to beta-hydroxy ketones and alpha-methylene ketones has been developed. Reaction of epoxy ketones with boron trifluoride etherate ((BF3OEt2)-O-.) generates the cationic intermediates by regioselective epoxide ring opening and an acyl shift. Then, a treatment of these cations with 2-aryl-1,3-dimethylbenzimidazolines (DMBIH) results in formation of 1,2-disubstituted 3-hydroxy ketones. DMBIH serves as a hydride donor in the second step of this process. Finally, the beta-hydroxy ketones can be converted to 1,2-disubstituted 2-methylene ketones by treatment with methanesulfonic acid or a combination of methanesulfonyl chloride and triethylamine. Importantly, the sequential steps involved in formation of the alpha-methylene ketone products can be carried out in one pot.