3-aminophenyl tosylate | 3865-15-4

• 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-aminophenyl tosylate
• 英文别名: 3-aminophenyl 4-methylbenzenesulfonate；3-aminophenyl p-toluenesulfonate；3-(p-toluene)sulfonyloxyaniline；m-(p-tolylsulphonyloxy)aniline；m-aminophenyl tosylate；3-(p-toluenesulfonyloxy)aniline；p-Toluenesulfonic acid 3-aminophenyl ester；(3-aminophenyl) 4-methylbenzenesulfonate
• CAS: 3865-15-4
• 化学式: C₁₃H₁₃NO₃S
• mdl: MFCD22014725
• 分子量: 263.317
• InChiKey: RUZVAAMFWWVKGG-UHFFFAOYSA-N

物化性质

• 熔点：
  92 - 95°C
• 溶解度：
  可溶于氯仿（轻微，加热），甲醇（轻微）

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  77.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2922199090

反应信息

• 作为反应物：
  描述：

  3-aminophenyl tosylate 在 camphor-10-sulfonic acid 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 苯 为溶剂， 反应 3.0h， 生成 3-(N-methyl-3'-p-toluenesulfonyloxyanilino)cyclohex-2-en-1-one
  参考文献：
  名称：

  Gardette, Daniel; Gramain, Jean-Claude; Lepage, Marie-Eve, Canadian Journal of Chemistry, 1989, vol. 67, p. 213 - 219

  摘要：

  DOI：
• 作为产物：
  描述：

  对甲苯磺酸-3-硝基苯酯 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 3-aminophenyl tosylate
  参考文献：
  名称：

  General-base catalysis by hydroxocopper(II) ion and existence of an addition intermediate in the hydrolysis of m-(2-imidazolylazo)phenyl p-toluenesulfonate

  摘要：

  Rates of the hydrolysis of m-(2-imidazolylazo)phenyl p-toluenesulfonate (1) were measured in the presence of Cu(II) ion. Saturation behavior was observed for the dependence on [Cu(II)] of the absorbance (Abs) of 1 or that of the pseudo-first-order rate constant (k0). The formation costant measured from the dependence on [Cu(II)] of k0 was much smaller than that of Abs. The binding constant reflected in the Abs data indicates the formation of a 1:1-type complex. The binding constant estimated with the k0 values may be related to the formation of a 2:1-type complex. This possibility, however, is excluded on the basis of the dependence of the binding constants on pH and the dependence of Abs on [Cu(II)]. Instead, the saturation kinetic behavior agrees with the shift of the rate-determining step between the formation and the breakdown processes of an intermediate upon increase in [Cu(II)]. On the basis of the kinetic data, it is shown that the 1:1-type complex is hydrated to form an addition intermediate, which is subsequently converted into the hydrolysis products, and that hydroxocopper(II) ion participates as a general-base catalyst in the rate-controlling proton-transfer process.

  DOI：

  10.1021/jo00014a009

文献信息

• A Mild and Efficient Palladium-Catalyzed Cyanation of Aryl Mesylates in Water or tBuOH/Water
  作者：Pui Yee Yeung、Chau Ming So、Chak Po Lau、Fuk Yee Kwong

  DOI：10.1002/anie.201005121

  日期：2010.11.15

  Cool and compatible: Aryl mesylates and tosylates underwent palladium‐catalyzed cyanation under mild, aqueous conditions at 65–80 °C (see scheme). In many cases, water could be used as the reaction medium without a cosolvent, and a variety of substituents R, such as keto, aldehyde, ester, free amine, and nitrile groups, remained intact during the transformation. Cy=cyclohexyl, Ms=methanesulfonyl,

  凉爽且相容：芳基甲磺酸酯和甲苯磺酸酯在65-80°C的温和水溶液条件下经历了钯催化的氰化反应（请参见方案）。在许多情况下，可以将水用作没有助溶剂的反应介质，并且在转化过程中，各种取代基R（例如酮，醛，酯，游离胺和腈基）保持完整。Cy =环己基，Ms =甲磺酰基，Ts =对甲苯磺酰基。
• Palladium-Catalyzed Phosphorylation of Aryl Mesylates and Tosylates
  作者：Wai Chung Fu、Chau Ming So、Fuk Yee Kwong

  DOI：10.1021/acs.orglett.5b03104

  日期：2015.12.4

  The first general palladium catalyst for the phosphorylation of aryl mesylates and tosylates is reported. The newly developed system exhibits excellent functional group compatibility. For instance, free amino, keto, ester, and amido groups, as well as heterocycles, remain intact during the course of reaction. The mesylated derivatives of biologically active compounds such as 17β-estradiol and 6-hydroxyflavone

  据报道，第一种用于芳基甲磺酸酯和甲苯磺酸酯磷酸化的通用钯催化剂。新开发的系统具有出色的功能组兼容性。例如，游离氨基，酮，酯和酰胺基以及杂环在反应过程中保持完整。还显示了生物活性化合物（如17β-雌二醇和6-羟基黄酮）的甲磺酸化衍生物是适用的底物。描述了一种一锅磷酸化-氨基化序列，可轻松合成潜在的药效基团。
• Palladium-Catalyzed Borylation of Aryl Mesylates and Tosylates and Their Applications in One-Pot Sequential Suzuki-Miyaura Biaryl Synthesis
  作者：Wing Kin Chow、Chau Ming So、Chak Po Lau、Fuk Yee Kwong

  DOI：10.1002/chem.201100361

  日期：2011.6.14

  Top of the one‐pots! The first palladium‐catalyzed borylation of aryl tosylates and mesylates is described. The reaction conditions are mild and provide excellent functional‐group compatibility (e.g., R=CN, CHO, COOMe, C(O)R, NH2, or NH‐indole; see scheme). Pd/MeO‐CM‐phos allows one‐pot sequential reactions in the preparation of unsymmetrical biaryls.

  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。
• Triple Mode of Alkylation with Ethyl Bromodifluoroacetate: <i>N</i> , or <i>O</i> ‐Difluoromethylation, <i>N</i> ‐Ethylation and <i>S</i> ‐(ethoxycarbonyl)difluoromethylation
  作者：Arghya Polley、Gurupada Bairy、Pritha Das、Ranjan Jana

  DOI：10.1002/adsc.201800824

  日期：2018.11.5

  chemical reactivity of ethyl bromodifluoroacetate. Typically, bromodifluoroacetic acid has been used as a difluorocarbene precursor for difluoromethylation of soft nucleophiles. Here we have disclosed nucleophilicity and base dependent divergent chemical reactivity of ethyl bromodifluoroacetate. It furnishes lithium hydroxide and cesium carbonate promoted difluoromethylation of tosyl‐protected aniline

  在这份报告中，我们探索了溴二氟乙酸乙酯的化学反应的三重模式。通常，溴二氟乙酸已被用作软亲核试剂的二氟甲基化的二氟卡宾前体。在这里，我们已经公开了溴二氟乙酸乙酯的亲核性和碱依赖性发散化学反应性。它提供了氢氧化锂和碳酸铯，分别促进了甲苯磺酰基保护的苯胺和缺电子的酚的二氟甲基化作用。有趣的是，将碱从氢氧化锂转变为4- N，N-二甲基氨基吡啶（DMAP）甲苯磺酰基保护的苯胺，得到了相应的N-乙基化产物。而高度亲核的苯硫酚提供了相应的S羰基乙氧基二氟甲基化产物在酯水解之前通过快速的S N 2攻击溴原子而形成。这种机制差异是通过几个控制实验确定的。结果表明，二氟甲基化反应是通过串联原位酯水解/脱羧-脱溴化二氟卡宾的形成并随后被软亲核试剂-NHTs或电子缺陷型酚-OH基团捕获而进行的。在DMAP的存在下，酯的水解受到干扰，相反，在乙基部分的亲核攻击提供了N-乙基化产物。因此，除了开发实用的碱促氮素胺和电
• N,N'-DIARYLUREA DERIVATIVE, MANUFACTURING METHOD THEREOF, AND THERMOSENSITIVE RECORDING MATERIAL USING SAME
  申请人：SANKO CO., LTD.

  公开号：US20210340099A1

  公开（公告）日：2021-11-04

  The present invention relates to an N,N′-diurea derivative represented by the following general formula (1) and a method for producing the same. In addition, the present invention relates to a thermosensitive recording material in which a thermosensitive recording layer including a basic dye which is colorless or lightly colored at room temperature and a developer capable of developing color upon contact with the basic dye by heating is provided on a base sheet, wherein the developer is the N,N′-diurea derivative represented by the following general formula (1): (wherein R2 is an alkyl group, an aralkyl group, or an aryl group; and A 1 is a hydrogen atom or an alkyl group).

  本发明涉及一种由以下一般式（1）表示的N,N′-二脲衍生物以及其制备方法。此外，本发明涉及一种热敏记录材料，其中在基底纸上提供了一个热敏记录层，该热敏记录层包括在室温下无色或轻染色的碱性染料和一种与碱性染料接触加热后能够显色的显色剂，其中显色剂为以下一般式（1）表示的N,N′-二脲衍生物：（其中R2为烷基、芳基烷基或芳基；A1为氢原子或烷基）。