4-methylphenoxyethyl 4-toluenesulfonate | 60225-66-3

• 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: 4-methylphenoxyethyl 4-toluenesulfonate
• 英文别名: 1-(toluene-4-sulfonyloxy)-2-p-tolyloxy-ethane；1-(Toluol-4-sulfonyloxy)-2-p-tolyloxy-aethan；2-(4-Methylphenoxy)ethyl 4-methylbenzenesulfonate
• CAS: 60225-66-3
• 化学式: C₁₆H₁₈O₄S
• 分子量: 306.383
• InChiKey: AXKRRLPNWOFMPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methylphenoxyethyl 4-toluenesulfonate 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 以0.44 g的产率得到4-tolyl vinyl ether
  参考文献：
  名称：

  芳基乙烯基醚的光化学自由基阳离子环加成

  摘要：

  在此，我们报道了使用芳基乙烯基醚作为自由基阳离子前体的 TiO 2光化学 [2+2] 和 [4+2] 环加成反应。通过这些自由基阳离子环加成，可以构建各种四元环和六元环。发现二烯比烯烃更亲自由基并且有效地捕获芳基乙烯基醚的自由基阳离子。

  DOI：

  10.1002/ejoc.202201207
• 作为产物：
  描述：

  2-[2-(4-Methylphenoxy)ethoxy]oxane 在 吡啶 、 甲醇 、 4-甲基苯磺酸吡啶 作用下， 反应 20.0h， 生成 4-methylphenoxyethyl 4-toluenesulfonate
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Aryloxyethyl Thiocyanate Derivatives against Trypanosoma cruzi

  摘要：

  As a continuation of our project aimed at the search for new and safe chemotherapeutic and chemoprophylactic agents against American trypanosomiasis (Chagas' disease), several drugs structurally related to 4-phenoxyphenoxyethyl thiocyanate (4) were designed, synthesized, and evaluated as antiproliferative agents against the parasite responsible for this disease, the hemoflagellated protozoan Trypanosoma cruzi. This thiocyanate derivative was previously shown to be an effective and potent agent against T. cruzi proliferation. Several drugs possessing thiocyanate groups proved to be effective growth inhibitors of T. cruzi growth. Among the designed compounds, it is important to point out the extremely potent activity shown by 11, 23, 38, 53, 90, 99, and 117 against the epimastigote forms of the parasite. All of them exhibited IC50 values in the low micromolar range, and these values were comparable with those presented by our lead drug 4 and ketokonazole, a well-known antiparasitic agent. The activity displayed by the nitrogen-containing derivative 90 was very promising with IC50 values of 3.3 muM. Several other thiocyanate derivatives also proved to be very potent inhibitors of the multiplication of T. cruzi epimastigotes, such as compounds 28, 33, 43, 48, 56, 61, 66, 71, 76, and 124. Compound 43 resulted in being a promising drug because it was also very effective against amastigotes, the clinically more relevant form of the parasite. This compound was Mold more potent than 4, while 11 showed nearly the same activity as our lead drug against intracellular T. cruzi. It was very surprising that the experimental juvenoid 124, although fairly devoid of activity against epimastigotes, was very effective against intracellular amastigotes growing in myoblasts. The rest of the designed compounds showed a broad degree of inhibitory action, from moderately active drugs to drugs almost devoid of antiparasitic activity. Compound 43 is an interesting example of an effective antichagasic agent that presents excellent prospectives not only as a lead drug but also to be used for further in vivo studies.

  DOI：

  10.1021/jm0201518

文献信息

• Recording materials
  申请人：FUJI PHOTO FILM CO., LTD.

  公开号：EP0219302A2

  公开（公告）日：1987-04-22

  A recording material contains an electron donating leuco dye and, as an electron accepting compound, a salicylic acid derivative having an alkyl group, an alkoxy group or an aryloxy group as a substituent or a metal salt thereof. The recording material has good color developability, working preservability and stability.

  一种记录材料含有一种电子供体白兰地染料，以及作为电子受体化合物的水杨酸衍生物（其取代基为烷基、烷氧基或芳氧基）或其金属盐。这种记录材料具有良好的显色性、工作保存性和稳定性。
• US4771034A
  申请人：——

  公开号：US4771034A

  公开（公告）日：1988-09-13
• Design, Synthesis, and Biological Evaluation of Aryloxyethyl Thiocyanate Derivatives against <i>Trypanosoma cruzi</i>
  作者：Eleonora Elhalem、Brian N. Bailey、Roberto Docampo、István Ujváry、Sergio H. Szajnman、Juan B. Rodriguez

  DOI：10.1021/jm0201518

  日期：2002.8.1

  As a continuation of our project aimed at the search for new and safe chemotherapeutic and chemoprophylactic agents against American trypanosomiasis (Chagas' disease), several drugs structurally related to 4-phenoxyphenoxyethyl thiocyanate (4) were designed, synthesized, and evaluated as antiproliferative agents against the parasite responsible for this disease, the hemoflagellated protozoan Trypanosoma cruzi. This thiocyanate derivative was previously shown to be an effective and potent agent against T. cruzi proliferation. Several drugs possessing thiocyanate groups proved to be effective growth inhibitors of T. cruzi growth. Among the designed compounds, it is important to point out the extremely potent activity shown by 11, 23, 38, 53, 90, 99, and 117 against the epimastigote forms of the parasite. All of them exhibited IC50 values in the low micromolar range, and these values were comparable with those presented by our lead drug 4 and ketokonazole, a well-known antiparasitic agent. The activity displayed by the nitrogen-containing derivative 90 was very promising with IC50 values of 3.3 muM. Several other thiocyanate derivatives also proved to be very potent inhibitors of the multiplication of T. cruzi epimastigotes, such as compounds 28, 33, 43, 48, 56, 61, 66, 71, 76, and 124. Compound 43 resulted in being a promising drug because it was also very effective against amastigotes, the clinically more relevant form of the parasite. This compound was Mold more potent than 4, while 11 showed nearly the same activity as our lead drug against intracellular T. cruzi. It was very surprising that the experimental juvenoid 124, although fairly devoid of activity against epimastigotes, was very effective against intracellular amastigotes growing in myoblasts. The rest of the designed compounds showed a broad degree of inhibitory action, from moderately active drugs to drugs almost devoid of antiparasitic activity. Compound 43 is an interesting example of an effective antichagasic agent that presents excellent prospectives not only as a lead drug but also to be used for further in vivo studies.
• Photochemical Radical Cation Cycloadditions of Aryl Vinyl Ethers
  作者：Sota Adachi、Genki Horiguchi、Hidehiro Kamiya、Yohei Okada

  DOI：10.1002/ejoc.202201207

  日期：2022.11.25

  TiO2 photochemical [2+2] and [4+2] cycloadditions using aryl vinyl ethers as radical cation precursors. The construction of various four- and six-membered rings is made possible by these radical cation cycloadditions. The diene is found to be more radicalophilic than the alkene and effectively traps the radical cation of the aryl vinyl ethers.

  在此，我们报道了使用芳基乙烯基醚作为自由基阳离子前体的 TiO 2光化学 [2+2] 和 [4+2] 环加成反应。通过这些自由基阳离子环加成，可以构建各种四元环和六元环。发现二烯比烯烃更亲自由基并且有效地捕获芳基乙烯基醚的自由基阳离子。