3-nitrophenyl methane sulfonate | 19013-29-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-nitrophenyl methane sulfonate
• 英文别名: 3-nitrophenyl methanesulfonate；nitrophenyl-m-mesylate；3-Nitrophenyl-methansulfonat；(3-nitrophenyl) methanesulfonate
• CAS: 19013-29-7
• 化学式: C₇H₇NO₅S
• 分子量: 217.202
• InChiKey: RAAALZBEKVQXSM-UHFFFAOYSA-N

物化性质

• 沸点：
  369.8±34.0 °C(Predicted)
• 密度：
  1.484±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  97.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-nitrophenyl methane sulfonate 在 双氧水 、 sodium hydroxide 作用下， 以 水 为溶剂， 生成 3-硝基苯酚阴离子
  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：

  间硝基苯酚 、 甲基磺酰氯 在 C₁₁H₁₈NO⁽¹⁺⁾*Cl^(1-)*2C₆H₁₅NO₃ 作用下， 以87 %的产率得到3-nitrophenyl methane sulfonate
  参考文献：
  名称：

  基于三乙醇胺的低共熔溶剂作为一种新型、生物相容性、可重复使用且高效的双催化剂/溶剂介质，用于苯酚的选择性甲苯磺酰化和甲磺酰化

  摘要：

  低共熔溶剂（DES）通常由氢键供体和氢键受体组成，由于其可调性、生物可降解性和合成成本低，最近被广泛研究为各种应用的有效且有用的溶剂。在这项工作中，我们通过热重分析（TGA）、傅里叶变换红外光谱（FT-IR）、差示扫描量热法（DSC）制备并鉴定了[苄基（2-羟乙基）二甲基氯化氮][三乙醇胺] 2作为一种新型DES。 )、循环伏安法 (CV)、氢电位 (pH)、折射率、粘度和电导率。该DES是一种可重复使用的催化剂/溶剂系统，用于在温和条件下选择性对苯酚进行甲苯磺酰化。这种 DES 可以轻松回收四次，而不会显着影响反应进度。该方案的优点是不存在任何添加剂、配体和金属，以及使用双溶剂/催化剂系统，包括易于制备、稳定性和可重复使用性、反应时间短和优异的产物产率。

  DOI：

  10.1016/j.tet.2023.133780

文献信息

• Late-Stage Aromatic C–H Oxygenation
  作者：Jonas Börgel、Lalita Tanwar、Florian Berger、Tobias Ritter

  DOI：10.1021/jacs.8b09208

  日期：2018.11.28

  Synthetic methods for oxidative aromatic C-O bond formation are sparse, despite their demand in metabolite synthesis for drug discovery and development. We report a novel methodology for late-stage C-O bond formation of arenes. The reaction proceeds with excellent functional group tolerance even for highly functionalized substrates. The resulting aryl mesylates provide access to potential human metabolites

  尽管在药物发现和开发中需要代谢物合成，但用于形成氧化芳族 CO 键的合成方法很少。我们报告了一种用于芳烃后期 CO 键形成的新方法。即使对于高度官能化的底物，该反应也以优异的官能团耐受性进行。所得的甲磺酸芳基酯提供了获取潜在的人类药物代谢物的途径，并可直接用于安装 CF 键以阻断代谢热点。试剂双（甲磺酰基）过氧化物和底物芳烃之间的电荷转移相互作用可能与芳烃相对于其他官能团的化学选择性官能化有关。
• Methanesulfonic acid/phosphorus oxychloride (MAPO) as a new efficient reagent in the Fries rearrangement
  作者：Babak Kaboudin

  DOI：10.1016/s0040-4020(99)00759-0

  日期：1999.10

  Methanesulfonic acid/phosphorus oxychloride (MAPO) was found to be a new effecient reagent in the Fries rearrangement of phenolic esters. Fries rearrangement of phenolic esters in the presence of MAPO, gave acylaryl methane sulfonates as major products.

  发现甲磺酸/氯氧化磷（MAPO）是酚酯的弗里斯重排中的一种新型高效试剂。在MAPO存在下，将酚酯进行弗里斯重排，得到酰基芳基甲烷磺酸盐作为主要产物。
• CH 3 SO 3 H/P 2 O 5 (4:1) As An Efficient Reagent for the One-Pot Synthesis of Acylaryl Methane Sulfonates of Phenolic
  作者：B. Kaboudin

  DOI：10.1080/10426500307808

  日期：2003.4

  Methansulfonic acid/di-phosphorus pentoxide (4:1) was found to be an efficient reagent for one-pot synthesis of acylaryl methane sulfonates of phenolic esters via Fries rearrangement. This method is easy, rapid, and high-yielding reactions for the synthesis of acylaryl methane sulfonates.

  甲磺酸/五氧化二磷 (4:1) 被发现是一种有效的试剂，用于通过 Fries 重排一锅法合成酚酯的甲磺酸酰基芳基酯。该方法是合成酰芳基甲磺酸酯的简单、快速和高产率的反应。
• [EN] KINASE INHIBITORS<br/>[FR] INHIBITEURS DE KINASE
  申请人：RESPIVERT LTD

  公开号：WO2014076484A1

  公开（公告）日：2014-05-22

  There are provided compounds of formula I, (I) wherein R1 to R5, Ar and X1 to X3 have meanings given in the description, which compounds have antiinflammatory activity (e.g. through inhibition of one or more of members of: the family of p38 mitogen-activated protein kinase enzymes; Syk kinase; and members of the Src family of tyrosine kinases) and have use in therapy, including in pharmaceutical combinations, especially in the treatment of inflammatory diseases, including inflammatory diseases of the lung, eye and intestines.

  提供了化合物I的化合物，化合物I的化合物中R1至R5，Ar以及X1至X3具有描述中给定的含义，这些化合物具有抗炎活性（例如通过抑制p38丝裂原活化蛋白激酶酶家族中的一个或多个成员；Syk激酶；以及酪氨酸激酶Src家族的成员之一）并且在治疗中有用，包括在药物组合中，特别是用于治疗炎症性疾病，包括肺部、眼睛和肠道的炎症性疾病。
• A Simple Preparation of Aryl Methanesulfonates by Thermal Decomposition of Dry Arenediazonium o-Benzenedisulfonimides in Methanesulfonic Acid
  作者：Margherita Barbero、Iacopo Degani、Stefano Dughera、Rita Fochi、Paolo Perracino

  DOI：10.1055/s-1999-3696

  日期：1999.1

  Aryl methanesulfonates 3 (18 examples) were easily prepared by thermal decomposition of dry arenediazonium o-benzene-disulfonimides 1 in methanesulfonic acid (2). The reactions were carried out at temperatures between 60 and 120 °C for times between 0.5 and 8 h. The aryl methanesulfonates were obtained in reproducible yield of 70-90%, with few exceptions. In all cases the o-benzenedisulfonimide (4) could be recovered in good yields which can then be reused to prepare the salts 1. When thermal decomposition of salts 1 was carried out in trifluoromethanesulfonic acid (5) at 90-120 °C for 1-2 h, aryl trifluoromethanesulfonates 6 were obtained in 73-78% yield (3 examples).

  芳基甲磺酸酯3（共18个实例）通过在甲磺酸（2）中热分解干燥的芳烃重氮 o-苯并二磺酰亚胺（1）而容易制备。反应温度在60至120°C之间，时间在0.5至8小时之间。芳基甲磺酸酯的可重复产率为70-90%，偶有例外。在所有情况下，o-苯并二磺酰亚胺（4）均可在良好收率下回收，随后可再用于制备盐1。当在90-120°C下于三氟甲磺酸（5）中对盐1进行热分解1-2小时后，得到芳基三氟甲磺酸酯6，收率为73-78%（共3个实例）。