3,5-dichloro-2-hydroxy-benzaldehyde-oxime | 5331-93-1

• 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: 3,5-dichloro-2-hydroxy-benzaldehyde-oxime
• 英文别名: 3,5-Dichlor-2-hydroxy-benzaldehyd-oxim；3,5-Dichlor-2-hydroxy-benzaldoxim；2,4-Dichloro-6-[(hydroxyimino)methyl]phenol；2,4-dichloro-6-(hydroxyiminomethyl)phenol
• CAS: 5331-93-1
• 化学式: C₇H₅Cl₂NO₂
• 分子量: 206.028
• InChiKey: SHGLQTKOGKFLAS-UHFFFAOYSA-N

物化性质

• 熔点：
  195-197 °C(Solv: chloroform (67-66-3))
• 沸点：
  315.2±42.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,5-dichloro-2-hydroxy-benzaldehyde-oxime 在 sodium hydroxide 、 氯 作用下， 以 乙醚 为溶剂， 生成 3,4-Bis-<3,5-dichlor-2-hydroxy-phenyl>-furoxan
  参考文献：
  名称：

  Infrared Spectra of the Nitrile N-Oxides: Some New Furoxans

  摘要：

  DOI：

  10.1021/jo01074a014
• 作为产物：
  描述：

  3,5-二氯水杨醛 在 乙醇 、 盐酸羟胺 、 水 作用下， 生成 3,5-dichloro-2-hydroxy-benzaldehyde-oxime
  参考文献：
  名称：

  Biltz; Stepf, Chemische Berichte, 1904, vol. 37, p. 4027

  摘要：

  DOI：

文献信息

• Oxime ethers and pesticidal preparations containing them
  申请人：Ciba-Geigy AG

  公开号：US03941839A1

  公开（公告）日：1976-03-02

  New oxime ethers and pesticidal and herbicidal preparations containing them are disclosed. The oxime ethers correspond to the formula ##SPC1## Wherein R.sub.1 is a hydrogen atom or a lower alkyl radical; R.sub.2 is an aliphatic, cycloaliphatic, araliphatic, aromatic or heterocyclic radical; or wherein R.sub.1 and R.sub.2 form part of a saturated or unsaturated carbocycle or a 5-, 6- or 7-membered heterocycle; R.sub.3 is a nitro, trifluoromethyl, formyl, lower carbalkoxy, sulfamyl or mono- or di-lower alkyl sulfamyl radical; R.sub.4.sub.- and R.sub.5.sub.- each is a hydrogen or halogen atom, an amino, mono- or di-lower alkyl amino, lower alkoxy, cycloalkoxy, lower alkylthio, nitro, lower carbalkoxy, arylthio, lower aralkylthio or lower alkyl group, or 5-, 6- or 7-membered heterocycle.

  揭示了新的肟醚化合物和含有它们的杀虫剂和除草剂制剂。这些肟醚化合物对应于以下结构式：其中R1为氢原子或较低的烷基基团；R2为脂肪族、环脂肪族、芳基脂肪族、芳香族或杂环基团；或者R1和R2构成饱和或不饱和的碳环或5、6或7元杂环的一部分；R3为硝基、三氟甲基、甲酰基、较低的羰基烷氧基、磺胺基或单或双较低的烷基磺胺基基团；R4和R5分别为氢或卤素原子、氨基、单或双较低的烷基氨基、较低的烷氧基、环烷氧基、较低的烷基硫氧基、硝基、较低的羰基烷氧基、芳基硫氧基、较低的芳基烷基硫氧基或较低的烷基基团，或者为5、6或7元杂环。
• 2-(Aminomethyl)phenols, a new class of saluretic agents. 1. Effects of nuclear substitution
  作者：G. E. Stokker、A. A. Deana、S. J. DeSolms、E. M. Schultz、R. L. Smith、E. J. Cragoe、J. E. Baer、C. T. Ludden、H. F. Russo

  DOI：10.1021/jm00186a024

  日期：1980.12

  A series of 2-(aminomethyl)phenols was synthesized and tested in rats and dogs for saluretic and diuretic activity. A number of these compounds exhibit a high order of activity on iv or po administration. The most active compounds belong to a subseries of 4-alkyl-6-halo derivatives of which 2, 2-(aminomethyl)-4-(1,1-dimethylethyl)-6-iodophenol, is the most active. Compound 2 also possesses significant

  合成了一系列2-（氨基甲基）酚，并在大鼠和狗中测试了其利尿和利尿活性。这些化合物中的许多在静脉内或口服给药时表现出高活性。活性最高的化合物属于4-烷基-6-卤代衍生物的子系列，其中2，2-（氨基甲基）-4-（1,1-二甲基乙基）-6-碘酚是最具活性的。化合物2还具有显着的降压活性，这是一种辅助药理参数，可将2与本系列制备的其他化合物区分开。此外，2显示局部利尿和抗炎活性。
• A stereoselective synthesis of symmetrical and unsymmetrical bibenzo[e][1,3]oxazine-2,2′-dione derivatives induced by low-valent titanium reagent
  作者：Guo-Lan Dou、Fang Sun、Da-Qing Shi

  DOI：10.1016/j.tet.2012.03.122

  日期：2012.6

  unsymmetrical bibenzo[e][1,3]oxazine-2,2′-dione derivatives were synthesized by the reaction of various o-hydroxy Schiff bases and triphosgene induced by low-valent titanium reagent (TiCl4/Sm). A variety of substrates can participate in the process with good yields. The present method provides a useful preparation of 3,3′,4,4′-tetrahydro-4,4′-bibenzo[e][1,3]oxazine-2,2′-dione derivatives, which cannot be

  低价钛试剂（TiCl 4 / Sm）诱导的各种邻羟基席夫碱与三光气反应合成了一系列对称和不对称的联苯并[ e ] [1,3]恶嗪-2,2'-二酮衍生物。）。多种底物可以高收率参与该过程。本方法提供了有用的3,3'，4,4'-四氢-4,4'-联苯并[ e ] [1,3]恶嗪-2,2'-二酮衍生物的制备方法，否则无法制备。反应的机理表明一锅参与还原，偶联和环化。
• Discovery of Natural Rosin Derivatives Containing Oxime Ester Moieties as Potential Antifungal Agents to Control Tomato Gray Mold Caused by <i>Botrytis cinerea</i>
  作者：Yanqing Gao、Renle Xu、Shihao Gu、Kun Chen、Jian Li、Xiaohua He、Shibin Shang、Zhanqian Song、Jie Song

  DOI：10.1021/acs.jafc.2c01532

  日期：2022.5.11

  series of dehydroabietyl oxime ester derivatives were synthesized using rosin as a raw material. Based on the evaluation and screening of in vitro antifungal activities against Botrytis cinerea (B. cinerea), Sclerotinia sclerotiorum, Valsa mali, Rhizoctonia solani, Fusarium oxysporum, and Alternaria alternata, compound 4f exhibited the best antifungal activity against B. cinerea, and its EC50 was 0.798

  受天然产物抗病原真菌应用的启发，以松香为原料合成了两个系列的脱氢枞基肟酯衍生物。通过对灰霉病菌、核盘菌、马里瓦尔萨、立枯病菌、尖孢镰刀菌和链格孢菌体外抗真菌活性的评价和筛选，化合物4f对灰霉病菌的抗真菌活性最好，其欧共体50为0.798 mg/L，低于阳性对照品醚菌酯（1.112 mg/L）。体内抗真菌活性结果表明，4f对番茄具有满意的保护和疗效。生理生化研究表明，化合物4f对灰霉病菌的作用机制是改变菌丝体的形态和超微结构，增加细胞膜的通透性，引起细胞核和线粒体功能障碍，从而导致细胞凋亡。此外，定性和定量构效关系研究表明，化合物4f之间的诱导和共轭相互作用与靶受体形成电子转移过程，从而达到抗真菌作用。这些结果表明，衍生自天然产物松香的化合物4f是一种新的潜在的抗灰霉病菌候选物。
• A Single-Reagent-Driven Multistep One-Pot Preparation of Thiazolines and 1,3-Thiazines from Aldoximes, Nitriles, and Carboxylic­ Acids
  作者：Uma Pathak、Shubhankar Bhattacharyya

  DOI：10.1055/s-0035-1560459

  日期：——

  N-(omega-Bromoalkyl)dichlorothiophosphoramidates have been designed as a new class of reagent for the single-reagent-driven multistep preparation of 2-substituted thiazolines and 1,3-thiazines from aldoximes, nitriles, or carboxylic acids. A wide range of substrates both aromatic as well as aliphatic were investigated and found suitable for the developed protocol.