18O-Phenacyl bromide

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 18O-Phenacyl bromide
• 英文别名: 2-bromo-1-phenylethan(18O)one
• 化学式: C₈H₇BrO
• 分子量: 201.048
• InChiKey: LIGACIXOYTUXAW-HRVHXUPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  苯乙炔 在 亚乙基硫脲 、 1,3-dibromo-5,5-dimethylhydantoin 、 重氧水 作用下， 以 丙酮 为溶剂， 生成 18O-Phenacyl bromide
  参考文献：
  名称：

  通过未活化炔烃与1,3-二卤代-5,5-二甲基乙内酰脲的催化级联反应，水控选择性制备[小α]-单或[小α] [小[伯或分钟]-二卤代酮

  摘要：

  已经开发了通过水控制的化学发散和区域​​特异性级联反应选择性合成[小α]-单或[小α]，[小α] [伯或分钟]-二卤代酮的有效方案。

  DOI：

  10.1039/c7gc00283a

文献信息

• Photocatalytic direct oxygen-isotopic labelings of carbonyls in ketones and aldehydes with oxygen-isotopic waters
  作者：Xianjin Zhu、Yong Liu、Lunyu Ou、Haijun Yang、Hua Fu

  DOI：10.1016/j.cclet.2023.108454

  日期：2023.11

  alkanesulfinates catalyzed this process. This strategy was extended to the in-situ formed ketones from the photocatalytic aerobic oxidation of alkyl arenes and secondary alcohols. Furthermore, reduction of the oxygen-isotopically labeled aldehydes with NaBH4 provided the corresponding oxygen-isotopically labeled primary alcohols. We believe that the oxygen-isotopically labeling method will be widely used in

  氧同位素标记在识别和理解化学和生物过程中发挥着重要作用。在一步中直接将 C=O 转化为 C= 18 O 或 C= 17 O 即可生成标记化合物，可以减轻合成负担，而无需重新合成。在这里，我们描述了一种光催化氧同位素标记方案，该方案可以通过与氧同位素水（H 2 18 O或H 2 17O）作为氧同位素的来源，其中光和氧赋能的烷亚磺酸钠催化了这一过程。该策略扩展到通过烷基芳烃和仲醇的光催化有氧氧化而原位形成的酮。此外，用NaBH 4还原氧同位素标记的醛提供相应的氧同位素标记的伯醇。我们相信氧同位素标记方法将在化学、生物学和医学领域得到广泛的应用。
• An 18O-Labeling Study of the .beta.-Nitroxyalkyl and .beta.-(Trifluoroacetoxy)alkyl Radical Migrations: Further Examples of a 1,2-Shift Mechanism
  作者：David Crich、G. Fredrick Filzen

  DOI：10.1021/jo00120a028

  日期：1995.7

  The results of an O-18 labeling study of the beta-(nitroxy)alkyl and beta-(trifluoroacetoxy)alkyl radical migrations are presented. Phenacyl bromide dimethyl acetal was hydrolyzed with (H2O)-O-18 water to give labeled phenacyl bromide and, following borohydride reduction, O-18 labeled styrene bromohydrin. Nitration and trifluoroacetylation gave the radical precursors which were allowed to react with tributyltin hydride and AIBN in benzene at reflux. After cleavage to 2-phenylethanol, the rearrangement products were examined by GC-MS. The beta-(nitroxy)alkyl migration is found to occur, in benzene to the extent of 64% through a 1,2-, as opposed to a 2,3-shift, mechanism. The beta-(trifluoroacetoxy)alkyl migration occurs 7% by the 1,2-pathway. It is suggested that, in general, faster ester migrations occur to a greater extent through the 1,2-shift pathway.
• Water-controlled selective preparation of α-mono or α,α′-dihalo ketones via catalytic cascade reaction of unactivated alkynes with 1,3-dihalo-5,5-dimethylhydantoin
  作者：Chao Wu、Xiu Xin、Zhi-Min Fu、Long-Yong Xie、Kai-Jian Liu、Zheng Wang、Wenyi Li、Zhi-Hui Yuan、Wei-Min He

  DOI：10.1039/c7gc00283a

  日期：——

  An efficient protocol for the selective synthesis of [small alpha]-mono or [small alpha],[small alpha][prime or minute]-dihalo ketones via a water-controlled chemodivergent and regiospecific cascade reaction has been developed.

  已经开发了通过水控制的化学发散和区域​​特异性级联反应选择性合成[小α]-单或[小α]，[小α] [伯或分钟]-二卤代酮的有效方案。