3-acetylphenyl mesylate | 1092513-16-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-acetylphenyl mesylate
• 英文别名: 3-acetylphenyl methanesulfonate；(3-Acetylphenyl) methanesulfonate
• CAS: 1092513-16-0
• 化学式: C₉H₁₀O₄S
• 分子量: 214.242
• InChiKey: ACMXSYFIKCQGDC-UHFFFAOYSA-N

物化性质

• 熔点：
  50.1-52.4 °C
• 沸点：
  374.7±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：

  3-acetylphenyl mesylate 在 双氧水 、 sodium hydroxide 作用下， 以 水 为溶剂， 生成 3-acetylphenoxide
  参考文献：
  名称：

  Pitfalls in Assessing the α-Effect: Reactions of Substituted Phenyl Methanesulfonates with HOO⁻, OH⁻, and Substituted Phenoxides in H₂O

  摘要：

  Toward resolving the current controversy regarding the validity of the a-effect, we have examined the reactions of Y-substituted phenyl methanesulfonates 1a-11 with HOO-, OH,- and Z-substituted phenoxides in the gas phase versus solution (H2O). Criteria examined in this work are the following: (1) Bronsted-type and Hammett plots for reactions with HOO- and OH-, (2) comparison of beta(lg) values reported previously for the reactions of Y-substituted phenyl benzenesulfonates 2a-2k with HOO- (beta(lg) = -0.73) and OH- (beta(lg) = -0.55), and for those of 1a-11 with HOO- (beta(lg) = -0.69) and OH- (beta(lg) = -1.35), and (3) Bronsted-type plot showing extreme deviation of OH- for reactions of 2,4-dintrophenyl methanesulfonate la with aryloxides, HOO-, and OH-, signifying extreme solvation vs different mechanisms. The results reveal significant pitfalls in assessing the validity of current interpretations of the alpha-effect. The extreme negative deviation by OH- must be due, in part, to the difference in their reaction mechanisms. Thus, the apparent dependence of the alpha-effect on leaving-group basicity found in this study has no significant meaning due to the difference in operating mechanisms. The current results argue in favor of a further criterion, i.e., a consistency in mechanism for the alpha-nucleophiles and normal nucleophiles.

  DOI：

  10.1021/jo101978x
• 作为产物：
  描述：

  3-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， 生成 3-acetylphenyl mesylate
  参考文献：
  名称：

  钯催化的甲磺酸烷基酯和甲苯磺酸酯的硼化反应及其在一锅顺序铃木-宫浦联芳的合成中的应用

  摘要：

  一锅之巅！描述了芳基甲苯磺酸盐和甲磺酸盐的第一个钯催化的硼化反应。反应条件温和，并具有出色的官能团相容性（例如，R = CN，CHO，COOMe，C（O）R，NH 2或NH-吲哚；请参见方案）。Pd / MeO-CM-phos可在不对称联芳烃的制备中进行一锅法依次反应。

  DOI：

  10.1002/chem.201100361

文献信息

• Palladium-Catalyzed <i>N</i>-Arylation of Sulfoximines with Aryl Sulfonates
  作者：Qingjing Yang、Pui Ying Choy、Qingyang Zhao、Man Pan Leung、Hoi Shan Chan、Chau Ming So、Wing-Tak Wong、Fuk Yee Kwong

  DOI：10.1021/acs.joc.8b01599

  日期：2018.9.21

  Palladium-catalyzed C–N bond coupling reaction between NH-sulfoximines and aryl halides (e.g., −Br, −I, and −Cl and pseudohalides −OTf and −ONf) was successfully achieved. Nevertheless, aryl tosylates/mesylates left much to be achieved. In this report, a general N-arylation of sulfoximines with aryl sulfonates is described. Using Pd(OAc)2/MeO-CM-phos complex, the N-aryl sulfoximine products can be

  钯催化的C-N键偶联反应之间NH -sulfoximines和芳基卤化物（例如，-Br，-I，-Cl和拟和-OTf和-ONf）被成功地实现。然而，芳基甲苯磺酸酯/甲磺酸酯仍然有很多待实现。在该报告中，描述了亚砜基亚砜与芳基磺酸酯的一般N-芳基化。使用Pd（OAc）2 / MeO-CM-phos络合物，可以以良好至优异的产率（高达99％）获得具有良好的常见官能团相容性的N-芳基亚磺酰亚胺产品。除芳烃部分外，链烯基甲苯磺酸盐被证明是成功的偶联伴侣。
• 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.
• Cross-Coupling of Mesylated Phenol Derivatives with Potassium Alkoxymethyltrifluoroborates
  作者：Gary A. Molander、Floriane Beaumard

  DOI：10.1021/ol201469r

  日期：2011.8.5

  Cross-coupling of mesylated phenol derivatives with various potassium alkoxymethyltrifluoroborates has been achieved. The corresponding aryl and heteroaryl alkoxymethyl compounds have been obtained with equal facility with both electron-rich and electron-poor substituents on the activated alcohol.
• A General Palladium-Catalyzed Suzuki-Miyaura Coupling of Aryl Mesylates
  作者：Chau Ming So、Chak Po Lau、Fuk Yee Kwong

  DOI：10.1002/anie.200803193

  日期：2008.10.6
• Suzuki–Miyaura Cross-Coupling Reactions of Potassium Boc-Protected Aminomethyltrifluoroborate with Aryl and Hetaryl Mesylates
  作者：Gary A. Molander、Inji Shin

  DOI：10.1021/ol301221p

  日期：2012.6.15

  Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions were studied with potassium Boc-protected aminomethyltrifluoroborate through C-O activation of various mesylate derivatives to afford the corresponding products in moderate to good yields.