ethyl 3-{[(4-methylphenyl)sulfonyl]oxy}benzoate | 443296-77-3

• 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: ethyl 3-{[(4-methylphenyl)sulfonyl]oxy}benzoate
• 英文别名: ethyl 3-(tosyloxy)benzoate；ethyl 3-(p-toluenesulfonyloxy)benzoate；Ethyl 3-[(4-methylbenzenesulfonyl)oxy]benzoate；ethyl 3-(4-methylphenyl)sulfonyloxybenzoate
• CAS: 443296-77-3
• 化学式: C₁₆H₁₆O₅S
• 分子量: 320.366
• InChiKey: ACDIDKZFZPBKSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3-{[(4-methylphenyl)sulfonyl]oxy}benzoate 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 76.0h， 生成 3-{[(4-methylphenyl)sulfonyl]oxy}benzoic acid 2-(2-cyanoethyl)hydrazide
  参考文献：
  名称：

  Synthesis and Biological Screening of 2-Substituted 5,6-Dihydro-5-oxo- 4H-1,3,4-oxadiazine-4-propanenitriles and of Their Intermediates

  摘要：

  To evaluate the effect of substituents on biological activities of electron-rich N-containing heterocycles, the variably 2-substituted 5,6-dihydro-5-oxo-4H-1,3,4-oxadiazine-4-propanenitriles 26-33 were synthesized and evaluated for antibacterial, antifungal, and enzyme-inhibition activities. The target compounds were obtained from alkyl 4- or 3-hydroxy benzoates 1 and 2, respectively, and from methyl indoleacetate 3. The phenolic OH group of benzoates I and 2 were substituted with p-toluenesulfonyl ( --> 4 and 5), benzoyl ( 6 and 7), and benzyl groups ( 8 and 9) and then converted to 5,6-dihydro-5-oxo-4H-1,3,4-oxadiazine-4-propanenitriles. To establish structure-activity relationships (SAR), a pharmacological screening of the intervening intermediates was also conducted, which revealed that the intermediate hydrazide 11 possesses significant antimicrobial and MAO-A inhibiting properties and intermediates 12,24,28, and 29 appreciable antifungal activities. Compound 7 inhibits a-chymotrypsin.

  DOI：

  10.1002/1522-2675(200202)85:2<559::aid-hlca559>3.0.co;2-a
• 作为产物：
  描述：

  3-羟基苯甲酸乙酯 、 对甲苯磺酰氯 在 三乙烯二胺 作用下， 以 二氯甲烷 为溶剂， 以81%的产率得到ethyl 3-{[(4-methylphenyl)sulfonyl]oxy}benzoate
  参考文献：
  名称：

  芳基甲苯磺酸盐与芳族羧酸盐的脱羧交叉偶联

  摘要：

  公开了双金属铜/钯催化剂体系，其能够在脱羧偶联反应中使用甲苯磺酸盐作为碳亲电体。各种芳香族羧酸盐，无论其取代方式如何，均已与这些廉价且易于获得的亲电试剂偶联，以高收率得到相应的联芳基化合物（参见方案）。

  DOI：

  10.1002/anie.200905953

文献信息

• Unified Protocol for Fe-Based Catalyzed Biaryl Cross-Couplings between Various Aryl Electrophiles and Aryl Grignard Reagents
  作者：Lei Wang、Yi-Ming Wei、Yan Zhao、Xin-Fang Duan

  DOI：10.1021/acs.joc.9b00151

  日期：2019.5.3

  Ti(OEt)4/PhOM enabled a highly general iron-based catalyst system, which could efficiently catalyze the biaryl coupling reaction between various electrophiles (I, Br, Cl, OTs, OCONMe2, OSO2NMe2) and common or functionalized aryl Grignard reagents with high functional group tolerance. Selective couplings of aryl iodides and bromides over the corresponding oxygen-based electrophiles have been achieved, and

  常用的FeCl 3 / SIPr与Ti（OEt）4 / PhOM的组合可实现高度通用的铁基催化剂体系，该体系可有效催化各种亲电试剂（I，Br，Cl，OTs，OCONMe 2， OSO 2 NMe 2）和具有高官能团耐受性的常用或官能化芳基格氏试剂。已经实现了芳基碘化物和溴化物在相应的基于氧的亲电试剂上的选择性偶联，因此，通过正交偶联策略方便地合成了阿尼芬净的三联苯甲酸中间体。
• Exploiting Aryl Mesylates and Tosylates in Catalytic Mono-α-arylation of Aryl- and Heteroarylketones
  作者：Wai Chung Fu、Chau Ming So、On Ying Yuen、Irene Toi Chuk Lee、Fuk Yee Kwong

  DOI：10.1021/acs.orglett.6b00643

  日期：2016.4.15

  The first general palladium catalyst for the catalytic mono-α-arylation of aryl- and heteroarylketones with aryl mesylates and tosylates is described. The newly developed indolyl-derived phosphine ligand L7 has been identified to promote this reaction efficiently. The key to success is attributed to the enhanced steric congestion of the catalyst and effective oxidative addition of the C(Ar)–OMs bond

  描述了用于芳基-和杂芳基酮与甲磺酸甲磺酸酯和甲苯磺酸酯的催化单-α-芳基化的第一种通用钯催化剂。已经确定了新开发的吲哚基衍生的膦配体L7可以有效地促进该反应。成功的关键归因于催化剂空间拥堵的增强和C （Ar） –OMs键的有效氧化加成。在Pd（OAc）2（0.25-2.5 mol％）和L7的存在下，选择性单芳基化反应可在足够的反应范围内实现，并且产物收率高达95％。重要的是，我们证明了该协议对生物酚类化合物的修饰的适用性，使其可用于酚类（前）药物的功能化。
• Regioselective Direct C-3 Arylation of Imidazo[1,2-<i>a</i>]pyridines with Aryl Tosylates and Mesylates Promoted by Palladium–Phosphine Complexes
  作者：Pui Ying Choy、Kwan Chak Luk、Yinuo Wu、Chau Ming So、Lai-lai Wang、Fuk Yee Kwong

  DOI：10.1021/jo502386w

  日期：2015.2.6

  Direct C-3 arylation of imidazo[1,2-a]pyridines with aryl tosylates and mesylates has been accomplished by employing palladium(II) acetate associated with SPhos (2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl) or L1 (2-(2-(diisopropylphosphino)phenyl)-1-methyl-1H-indole). This catalyst system can be applied to a wide range of aryl sulfonates and shows excellent C-3 regioselectivity of imidazo[1,2-a]pyridine

  咪唑并直接C-3的芳基化[1,2一]吡啶与芳基甲苯磺酸酯和甲磺酸酯已通过采用钯完成（II）与SPhos（2-二环己基膦基-2'，6'-二甲氧基联苯）或相关联的醋酸L1（2 -（2-（二异丙基膦基）苯基）-1-甲基-1 H-吲哚）。该催化剂体系可用于各种芳基磺酸盐，并显示出优异的咪唑并[1,2- a ]吡啶的C-3区域选择性。这些结果代表了使用甲苯磺酸酯和甲磺酸酯官能化的芳烃作为该区域选择性直接芳基化的亲电子伙伴的第一个例子。
• Palladium-Catalyzed Monoarylation of Arylhydrazines with Aryl Tosylates
  作者：Yange Huang、Pui Ying Choy、Junya Wang、Man-Kin Tse、Raymond Wai-Yin Sun、Albert Sun-Chi Chan、Fuk Yee Kwong

  DOI：10.1021/acs.joc.0c01599

  日期：2020.11.20

  A palladium-catalyzed C–N bond coupling reaction between arylhydrazines and aryl tosylates for facile synthesis of unsymmetrical N,N-diarylhydrazines has been developed. Employing the catalyst system of Pd(TFA)2 associated with newly developed phosphine ligand L1, the monoarylation of arylhydrazine proceeds smoothly to afford desired products in good-to-excellent yields (up to 95%) with good functional

  已开发了钯催化的芳基肼与芳基甲苯磺酸酯之间的C–N键偶联反应，可轻松合成不对称的N，N-二芳基肼。利用与新开发的膦配体L1关联的Pd（TFA）2催化剂体系，芳基肼的单芳基化反应顺利进行，以良好的产率（高达95％）提供了具有良好官能团相容性的所需产品。该方法提供了从简单且容易获得的偶联组分中获得结构多样的N，N-二芳基肼的替代合成途径。
• Nickel-Catalyzed Decarboxylative Coupling of Alkynyl Carboxylates with Aryl Tosylates and Mesylates
  作者：Dipannita Kalyani、Anna Howard、Samantha Klemann、Sarah Kolling、Katrina Little、Erin Plasek

  DOI：10.1055/s-0037-1609636

  日期：2019.4

  § These authors contributed equally Abstract A method for the nickel-catalyzed coupling of alkynyl carboxylates or acids with aryl tosylates and mesylates is described. Electronically varied carboxylates and aryl electrophiles participate in these transformations to afford the desired diarylalkyne products. In general, electrophiles bearing an extended π-system lead to products in higher yields than

  §这些作者做出了同等贡献 抽象的 描述了一种用于炔基羧酸盐或酸与芳基甲苯磺酸盐和甲磺酸盐的镍催化偶联的方法。电子变化的羧酸盐和芳基亲电试剂参与这些转化，以提供所需的二芳基炔烃产物。通常，与仅具有一个芳环的磺酸盐相比，带有扩展π系统的亲电试剂可产生更高的收率。 描述了一种用于炔基羧酸盐或酸与芳基甲苯磺酸盐和甲磺酸盐的镍催化偶联的方法。电子变化的羧酸盐和芳基亲电试剂参与这些转化，以提供所需的二芳基炔烃产物。通常，与仅具有一个芳环的磺酸盐相比，带有扩展π系统的亲电试剂可产生更高的收率。