4-{[(4-methylphenyl)sulfonyl]oxy}benzoic acid hydrazide | 443296-78-4

• 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: 4-{[(4-methylphenyl)sulfonyl]oxy}benzoic acid hydrazide
• 英文别名: 4-(tosyloxy)benzohydrazide；4-(Hydrazinecarbonyl)phenyl 4-methylbenzene-1-sulfonate；[4-(hydrazinecarbonyl)phenyl] 4-methylbenzenesulfonate
• CAS: 443296-78-4
• 化学式: C₁₄H₁₄N₂O₄S
• 分子量: 306.342
• InChiKey: UXOHMFDXMQKSJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-{[(4-methylphenyl)sulfonyl]oxy}benzoic acid hydrazide 在 tris(acetonitrile)(η5-pentamethylcyclopentadienyl)rhodium(III) hexafluoroantimonate 、 silver(I) acetate 、 potassium carbonate 、 三乙胺 、 对甲苯磺酰氯 、 苯氧乙酸 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 、 均三甲苯 为溶剂， 反应 30.0h， 生成 (2s*,3aR*,3a¹r*,5E,9E,10aS*)-ethyl 5,9-dibenzylidene-3a,10a-dimethyl-7-(tosyloxy)-2,3,3a,4,5,9,10,10a-octahydro-1H-2,3a¹-epoxypyrene-2-carboxylate
  参考文献：
  名称：

  通过串联C–H活化/分子内Diels–Alder / 1,3-偶极环加成反应一锅合成十氢py

  摘要：

  已成功开发了一种新颖的十氢involving合成方法，该方法以重氮为直接基，通过串联铑催化的C–H活化/分子间Diels–Alder反应/ 1,3-偶极环加成级联过程。这种一站式策略的优势是非常简单，高效，高度立体选择性和独特的产品结构。

  DOI：

  10.1021/acs.orglett.6b02768
• 作为产物：
  描述：

  methyl 4-(tosyloxy)benzoate 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 28.0h， 以63%的产率得到4-{[(4-methylphenyl)sulfonyl]oxy}benzoic acid 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

文献信息

• Design, Synthesis, and Study of the Insecticidal Activity of Novel Steroidal 1,3,4-Oxadiazoles
  作者：Shichuang Ma、Weiqi Jiang、Qi Li、Tian Li、Wenjun Wu、Hangyu Bai、Baojun Shi

  DOI：10.1021/acs.jafc.1c00088

  日期：2021.10.6

  was designed and synthesized, and the target compounds were evaluated for their insecticidal activity against five aphid species. Most of the tested compounds exhibited potent insecticidal activity against Eriosoma lanigerum (Hausmann), Myzus persicae, and Aphis citricola. Compounds 20g and 24g displayed the highest activity against E. lanigerum, showing LC50 values of 27.6 and 30.4 μg/mL, respectively

  设计并合成了一系列具有取代的1,3,4-恶二唑结构的新型甾体衍生物，并评估了目标化合物对五种蚜虫的杀虫活性。大多数测试的化合物表现出对鼠尾草（Hausmann）、桃蚜和柑橘蚜的有效杀虫活性。化合物20g和24g对E. lanigerum 的活性最高，LC 50值分别为 27.6 和 30.4 μg/mL。E. lanigerum中肠细胞的超微结构变化通过透射电子显微镜检测，表明这些甾体恶唑衍生物可能通过破坏昆虫中肠细胞的线粒体和核膜来发挥其杀虫活性。此外，田间试验表明，化合物20g表现出与阳性对照毒死蜱和噻虫嗪对E. lanigerum的效果相似，在200 μg/mL剂量下21天后达到89.5%的控制率。我们还通过测定三种杀虫剂解毒酶的活性研究了E. lanigerum 中目标化合物的水解和代谢。复合物20g50 μg/mL 对羧酸酯酶的抑制作用类似于已知的抑制剂磷酸三苯酯。上述结果证明了
• .BETA.-N-Cyanoethyl Acyl Hydrazide Derivatives: A New Class of .BETA.-Glucuronidase Inhibitors.
  作者：Khalid Mohammed Khan、Shahida Shujaat、Shagufta Rahat、Safdar Hayat、Atta-ur-Rahman、Muhammad Iqbal Choudhary

  DOI：10.1248/cpb.50.1443

  日期：——

  Eight new β-N-substituted acyl hydrazides along with their corresponding acyl derivatives were synthesized and screened for in vitro β-glucuronidase inhibition and found to be active against the enzyme. All of these compounds were found to be noncompetitive inhibitors except for N′-(2-cyanoethyl)-4-hydroxy benzohydrazide (10), which was found to be an uncompetitive inhibitor. Structure–activity relationship studies indicated that the benzyloxy group present in compounds 12 and 13 is responsible for the β-glucuronidase inhibition activity.

  合成了八种新的β-N-取代酰肼及其相应的酰基衍生物，并对它们进行了体外β-葡萄糖苷酶抑制活性筛选，发现它们对酶具有活性。除了N'-(2-氰乙基)-4-羟基苯甲酼肼（10）被发现是非竞争性抑制剂外，所有这些化合物都被发现是非竞争性抑制剂。结构-活性关系研究表明，化合物12和13中的苄氧基是导致β-葡萄糖苷酶抑制活性的原因。
• Synthesis and Biological Screening of 2-Substituted 5,6-Dihydro-5-oxo- 4H-1,3,4-oxadiazine-4-propanenitriles and of Their Intermediates
  作者：Khalid Mohammed Khan、Shagufta Rahat、Muhammad Iqbal Choudhary、Atta-ur-Rahman、Usman Ghani、Shahnaz Perveen、Shagufta Khatoon、Ahsana Dar、Abdul Malik

  DOI：10.1002/1522-2675(200202)85:2<559::aid-hlca559>3.0.co;2-a

  日期：2002.2

  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.
• One-Pot Synthesis of Decahydropyrene via Tandem C–H Activation/Intramolecular Diels–Alder/1,3-Dipolar Cycloaddition
  作者：Hui Lin、Lin Dong

  DOI：10.1021/acs.orglett.6b02768

  日期：2016.11.4

  A novel decahydropyrene synthesis has been successfully developed involving a tandem rhodium-catalyzed C–H activation/intramolecular Diels–Alder reaction/1,3-dipolar cycloaddition cascade process by using diazole as a traceless directing group. The advantage of this one-pot strategy is a quite simple, efficient, highly stereoselective, and unique product structure.

  已成功开发了一种新颖的十氢involving合成方法，该方法以重氮为直接基，通过串联铑催化的C–H活化/分子间Diels–Alder反应/ 1,3-偶极环加成级联过程。这种一站式策略的优势是非常简单，高效，高度立体选择性和独特的产品结构。