4-氯-3-乙基-1-甲基吡唑-5-甲酸乙酯 | 124800-34-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-氯-3-乙基-1-甲基吡唑-5-甲酸乙酯
• 英文名称: ethyl 4-chloro-3-ethyl-1-methyl-1H-pyrazole-5-carboxylate
• 英文别名: Ethyl 1-methyl-3-ethyl-4-chloro-5-pyrazolecarboxylate；ethyl 4-chloro-5-ethyl-2-methylpyrazole-3-carboxylate
• CAS: 124800-34-6
• 化学式: C₉H₁₃ClN₂O₂
• 分子量: 216.667
• InChiKey: CUKJHWLTDJWPHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-氯-3-乙基-1-甲基吡唑-5-甲酸乙酯 在 氯化亚砜 、 三乙胺 、 sodium hydroxide 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 4.0h， 生成 4-chloro-N-[2-chloro-1-(4-pentoxyphenyl)ethyl]-5-ethyl-2-methylpyrazole-3-carboxamide
  参考文献：
  名称：

  Design, Synthesis, and Insecticidal Activity of Novel Pyrazole Derivatives Containing α-Hydroxymethyl-N-benzyl Carboxamide, α-Chloromethyl-N-benzyl Carboxamide, and 4,5-Dihydrooxazole Moieties

  摘要：

  On the basis of commercial insecticides tebufenpyrad and tolfenpyrad, two series of novel pyrazole-5-carboxamides containing alpha-hydroxymethyl-N-benzyl or alpha-chloromethyl-N-benzyl and pyrazoles containing 4,5-dihydrooxazole moieties were designed and synthesized via the key intermediate 2-amino-1-(4-substituted) phenyl ethanol. The structures of target compounds were confirmed by H-1 NMR and elemental analysis or high-resolution mass spectrum (HRMS), and their activities against cotton bollworm (Helicoverpa armigera), diamondback moth (Plutella xylostella), bean aphid (Aphis craccivora), mosquito (Culex pipiens pallens), and spider mite (Tetranychus cinnabarinus) were tested. The results of bioassays indicated that compounds containing alpha-diloromethyloN-benzyl and compounds containing 4,5-dihydrooxazole showed high insecticidal activity against cotton bollworm. Especially, stomach activities of compounds Ij, Il, and IIe were 60% at 5 mg kg(-1). Moreover, the target compounds exhibited high selectivity between cotton bollworm and diamondback moth, although both of them belong to the order Lepidoptera. Although the activities against diamondback moth were at a low level, some of the target compounds exhibited antifeedant activity. The compounds also had good activities against bean aphid, mosquito, and spider mite. The foliar contact activity of compounds Ic, Id, le, and IIf against bean aphid were 95, 95, 100, and 95%, respectively, at 200 mg kg(-1). The miticidal and ovicidal activities of compound IIi against spider mite were both 95% at 200 mg kg(-1). Furthermore, a trivial change at 4-position of pyrazole ring would lead to great changes in properties and activities, which can easily be deduced by comparing the activities of compounds in series I (4-chloro-pyrazole compounds) with corresponding compounds in series II (4-hydro-pyrazole compounds), especially from the miticidal and ovicidal activities of Ii and IIi against spider mite.

  DOI：

  10.1021/jf204778v
• 作为产物：
  描述：

  2,4-二氧代己酸乙酯 在 磺酰氯 、 一水合肼 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 9.0h， 生成 4-氯-3-乙基-1-甲基吡唑-5-甲酸乙酯
  参考文献：
  名称：

  含有吡唑环的 1,2,4-恶二唑取代苯甲酰胺类似物的基于结构的生物等排性设计、合成、生物活性和毒性

  摘要：

  为了发现具有高活性和低毒性的农药先导化合物，通过生物等排性设计了一系列被吡唑连接的1,2,4-恶二唑取代的新型苯甲酰胺。目标化合物的化学结构通过1 H NMR、13 C NMR 和 HRMS 分析确定。初步生物测定表明，大多数化合物在 500 mg/L 时对Mythimna separate、Helicoverpa armigera、Ostrinia nubilalis和Spodoptera frugiperda表现出良好的致死活性。特别是在Mythimna separate的情况下，化合物14q (70%) 表现出明显的杀虫活性。此外，化合物14h对稻瘟病菌表现出良好的杀菌活性，抑制率为77.8%，化合物14e、14k、14n和14r也显示出一定的抗真菌活性（55.6-66.7%）。斑马鱼毒性试验表明化合物14h的LC 50为14.01 mg/L，表明其可作为进一步结构优化的潜在先导化合物。

  DOI：

  10.3390/molecules27154692

文献信息

• Development of novel bis-pyrazole derivatives as antitumor agents with potent apoptosis induction effects and DNA damage
  作者：Hong Dai、Shushan Ge、Jing Guo、Shi Chen、Meiling Huang、Jiaying Yang、Siyu Sun、Yong Ling、Yujun Shi

  DOI：10.1016/j.ejmech.2017.11.098

  日期：2018.1

  A series of bis-pyrazole derivatives were designed and synthesized, and their antitumor effects in vitro and in vivo were investigated. Several compounds displayed good antiproliferative activity with IC50 values in low-micromolar range against three human cancer cell lines in vitro, superior to 5-FU. The most potent compound 10M selectively inhibited human hepatocellular carcinoma cells but not non-tumor

  一系列双-吡唑衍生物的设计和合成，并且它们的抗肿瘤作用在体外和体内进行了研究。几种化合物在体外对三种人类癌细胞系均表现出良好的抗增殖活性，其IC 50值在低微摩尔范围内，优于5-FU。最有效的化合物10M在体外选择性抑制人肝癌细胞，但不抑制非肿瘤肝细胞增殖，并通过以浓度依赖性方式裂解PARP和caspase-3来显着触发SMMC-7721细胞凋亡。进一步的研究表明，强效活性对细胞生长具有抑制和凋亡诱导作用。10M与DNA损伤和p53信号通路的激活有关。此外，10M表现出对小鼠的低急性毒性，并且在体内对肝癌肿瘤具有显着的生长抑制作用。
• 吡唑酰胺类化合物及其制备方法与应用
  申请人：湖南化工研究院有限公司

  公开号：CN106608873B

  公开（公告）日：2019-05-24

  本发明公开了式(I)所示的吡唑酰胺类化合物及其制备方法与应用。式中R、R1、R2、W具有说明书中所给定义。本发明式(I)化合物具有杀菌、杀虫或杀螨生物活性，尤其是对病原菌如白粉病菌、灰霉病菌和锈病等具有很高的活性。
• 一种二氟苯基噁二唑类杀虫杀螨剂
  申请人：青岛科技大学

  公开号：CN109320506B

  公开（公告）日：2021-09-21

  本发明提供了一种二氟苯基噁二唑类化合物，结构如通式I所示：式中：R1选自甲基或乙基；R2选自甲基、乙基或叔丁基；R3选自H或Cl。通式Ⅰ化合物对害虫、害螨有抑杀作用，可作为杀虫剂、杀螨剂用于农业虫害、螨害的防治。
• Design, Synthesis, and Acaricidal Activities of Novel Pyrazole Acrylonitrile Compounds
  作者：Danling Huang、Mingzhi Huang、Aiping Liu、Xingping Liu、Weidong Liu、Xiaoyang Chen、Hansong Xue、Jiong Sun、Dulin Yin、Xiaoguang Wang

  DOI：10.1002/jhet.2682

  日期：2017.3

  Using cyenopyrafen as the lead compound, a series of novel pyrazole acrylonitrile compounds were designed and synthesized via the reaction of butylphenylacetonitrile with the corresponding (substituted pyrazol‐5‐yl) methanone of pyrethroid alcohols in the presence of potassium tert‐butoxide. These compounds showed prominent acaricidal activity against Tetranchus urticae. In particular, IIf, IIh, IIo

  在叔丁醇钾存在下，通过丁基苯基乙腈与拟除虫菊酯醇的相应（取代的吡唑-5-基）甲酮反应，以氰基吡喃苯甲醛为主要化合物，设计和合成了一系列新型的吡唑丙烯腈化合物。这些化合物表现出明显的对毛螨的杀螨活性。特别地，I如果，IIH，IIO，和IIP显示极好的活性，其中所述中值致死浓度均低于0.4毫克/升。此外，还讨论了目标化合物的构效关系。
• Design, synthesis, DFT study and antifungal activity of the derivatives of pyrazolecarboxamide containing thiazole or oxazole ring
  作者：Zhongzhong Yan、Aiping Liu、Mingzhi Huang、Minhua Liu、Hui Pei、Lu Huang、Haibo Yi、Weidong Liu、Aixi Hu

  DOI：10.1016/j.ejmech.2018.02.036

  日期：2018.4

  Pyrazolecarboxamide fungicides are one of the most important classes of agricultural fungicides, which belong to succinodehydrogenase inhibitors (SDHIS). To discover new pyrazolecarboxamide analogues with broad spectrum and high activity, a class of new compounds of pyrazole carboxamide derivatives containing thiazole or oxazole ring were designed by scaffold hopping and bioisosterism, and 36 pyrazole

  吡唑甲酰胺类杀菌剂是最重要的农业杀菌剂之一，属于琥珀酸脱氢酶抑制剂（SDHIS）。为发现具有广谱和高活性的新型吡唑羧酰胺类似物，通过支架跳跃和生物立体异构化设计了一类新型的含噻唑或恶唑环的吡唑羧酰胺衍生物，合成了36种具有抗真菌活性的吡唑羧酰胺衍生物。对这些化合物针对五种植物病原真菌，玉米赤霉菌，辣椒疫霉菌，菌核盘菌，小粒小麦和高粱锈菌进行了评估。结果表明，大多数化合物表现出良好的杀真菌活性，特别是对E. graminis。理论计算是在B3LYP / 6-31G上进行的（d，