2-acetylphenyl methanesulfonate | 99179-74-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetylphenyl methanesulfonate
• 英文别名: 2-acetylphenyl mesylate；1-(2-methanesulfonyloxy-phenyl)-ethanone；1-(2-Methansulfonyloxy-phenyl)-aethanon；(2-acetylphenyl) methanesulfonate
• CAS: 99179-74-5
• 化学式: C₉H₁₀O₄S
• 分子量: 214.242
• InChiKey: CJLQSVBVHZXFDG-UHFFFAOYSA-N

物化性质

• 沸点：
  364.8±34.0 °C(Predicted)
• 密度：
  1.290±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-acetylphenyl methanesulfonate 在 吡啶 、 氢氧化钾 作用下， 生成 4-methyl-1,2-benzoxathiine 2,2-dioxide
  参考文献：
  名称：

  Philbin et al., Journal of the Chemical Society, 1956, p. 4414,4416

  摘要：

  DOI：
• 作为产物：
  描述：

  2'-羟基苯乙酮 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以97%的产率得到2-acetylphenyl methanesulfonate
  参考文献：
  名称：

  薄片蛋白生物碱的有效合成：薄片蛋白G三甲醚的合成

  摘要：

  描述了薄片蛋白生物碱的一般和有效的合成。合成涉及形成吡咯并[2，1- a ]异喹啉核心，然后形成内酯环。

  DOI：

  10.1016/s0040-4039(00)02222-x

文献信息

• Direct Transformation of Ethylarenes into Primary Aromatic Amides with <i>N</i>-Bromosuccinimide and I₂–Aqueous NH₃
  作者：Shohei Shimokawa、Yuhsuke Kawagoe、Katsuhiko Moriyama、Hideo Togo

  DOI：10.1021/acs.orglett.6b00048

  日期：2016.2.19

  α-bromomethyl ketones and/or aryl methyl ketones were formed at the first reaction step and their iodoform-type reaction occurred at the second reaction step to provide primary aromatic amides. The present reaction is a useful and practical transition-metal-free method for the preparation of primary aromatic amides from ethylarenes.

  通过在乙酸乙酯和水，乙腈和水的混合物中催化量的2,2'-偶氮二（异丁腈）存在下用N-溴琥珀酰亚胺处理，将各种乙基芳烃高收率转化为相应的伯芳族酰胺。，或氯仿和水，然后在一个锅中与分子碘和NH 3水溶液反应。发现在第一反应步骤中形成芳基α-溴甲基酮和/或芳基甲基酮，并且在第二反应步骤中发生它们的碘仿型反应以提供伯芳族酰胺。本反应是用于从乙基芳烃制备伯芳族酰胺的有用且实用的无过渡金属的方法。
• Antifungal Triazole Derivatives
  申请人：Park Joon Seok

  公开号：US20080194661A1

  公开（公告）日：2008-08-14

  Disclosed herein are antifungal triazole derivatives or pharmaceutically acceptable salts thereof, a preparation method thereof, and a pharmaceutical composition comprising the same.

  本文揭示了抗真菌三唑衍生物或其药用盐，其制备方法，以及包含它们的药物组合物。
• Chromatography-Free and Eco-Friendly Synthesis of Aryl Tosylates and Mesylates
  作者：Xiangyang Lei、Anusha Jalla、Mhd Abou Shama、Jamie Stafford、Billy Cao

  DOI：10.1055/s-0034-1378867

  日期：——

  Two chromatography-free and eco-friendly protocols have been developed to synthesize aryl tosylates and mesylates by the tosylation and mesylation of the corresponding hydroxyarenes, respectively. These protocols are superior to other known ones regarding the simplicity, reaction time and conditions, the range of substrates, yields, and environmental friendliness.
• Method for preparation of 4-methyl-1,2-benzoxathiine 2,2-dioxide derivatives
  作者：A. Grandāne、A. F. Mishnev、I. V. Vozny、R. Žalubovskis

  DOI：10.1007/s10593-012-1087-y

  日期：2012.9
• Mapping Dual‐Base‐Enabled Nickel‐Catalyzed Aryl Amidations: Application in the Synthesis of 4‐Quinolones
  作者：Ryan T. McGuire、Travis Lundrigan、Joshua W. M. MacMillan、Katherine N. Robertson、Arun A. Yadav、Mark Stradiotto

  DOI：10.1002/anie.202200352

  日期：2022.3.21

  AbstractThe C−N cross‐coupling of (hetero)aryl (pseudo)halides with NH substrates employing nickel catalysts and organic amine bases represents an emergent strategy for the sustainable synthesis of (hetero)anilines. However, unlike protocols that rely on photoredox/electrochemical/reductant methods within NiI/III cycles, the reaction steps that comprise a putative Ni0/II C−N cross‐coupling cycle for a thermally promoted catalyst system using organic amine base have not been elucidated. Here we disclose an efficient new nickel‐catalyzed protocol for the C−N cross‐coupling of amides and 2′‐(pseudo)halide‐substituted acetophenones, for the first time where the (pseudo)halide is chloride or sulfonate, which makes use of the commercial bisphosphine ligand PAd2‐DalPhos (L4) in combination with an organic amine base/halide scavenger, leading to 4‐quinolones. Room‐temperature stoichiometric experiments involving isolated Ni0, I, and II species support a Ni0/II pathway, where the combined action of DBU/NaTFA allows for room‐temperature amide cross‐couplings.