[4-(4-chloro-phenyl)-5-oxo-4,5-dihydro-tetrazol-1-yl]-acetic acid ethyl ester | 928342-80-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [4-(4-chloro-phenyl)-5-oxo-4,5-dihydro-tetrazol-1-yl]-acetic acid ethyl ester
• 英文别名: ethyl 2-[4-(4-chlorophenyl)-5-oxo-1,4-dihydro-5H-tetrazol-1-yl]acetate；Ethyl 2-[4-(4-chlorophenyl)-5-oxotetrazol-1-yl]acetate
• CAS: 928342-80-7
• 化学式: C₁₁H₁₁ClN₄O₃
• 分子量: 282.686
• InChiKey: HWUJMAKGRBIRBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  74.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [4-(4-chloro-phenyl)-5-oxo-4,5-dihydro-tetrazol-1-yl]-acetic acid ethyl ester 在 氢氧化钾 、 potassium carbonate 、 一水合肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 52.0h， 生成 1-(4-Chlorophenyl)-4-[(5-hexylsulfanyl-1,3,4-thiadiazol-2-yl)methyl]tetrazol-5-one
  参考文献：
  名称：

  Discovery of a new insecticide lead by optimizing a target-diverse scaffold: Tetrazolinone derivatives

  摘要：

  In order to discover lead compounds with novel action mechanism, a series of tetrazolinone derivatives bearing structurally diverse substituents, 1-aryl-4-substituted-1,4-di-hydro-5H-tetrazol-5-ones 2, 1-((5-(alkylthio)-1,3,4-oxadiazol-2-yl)methyl)-4-(substituted)- phenyl-1H-tetrazol-5(4H)-ones 5, and 1-((5-(alkylthio)-1,3,4-thiadiazol-2-yl)methyl)-4-(substituted)phenyl-1H-tetrazol5(4H)-ones 7, were designed and synthesized in good yields by a multiple-step synthetic procedure. The results of greenhouse in vivo test indicated that all the target compounds did not displayed herbicidal activity, however, some of them exhibited excellent in vivo insecticidal activity against Tetranychus cinnabarinus at the concentration of 250 mg L-1. To our knowledge, this is the first report about the insecticidal activity of tetrazolinone derivatives, which indicated that the tetrazolinone scaffold could be identified as a novel insecticidal lead structure. The present work demonstrated that optimizing a target-diverse scaffold is an effective way to discover new lead compounds with new action mechanism or biological activity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.12.002
• 作为产物：
  描述：

  1-(4-氯苯基)-2H-四唑-5-酮 、 溴乙酸乙酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以90%的产率得到[4-(4-chloro-phenyl)-5-oxo-4,5-dihydro-tetrazol-1-yl]-acetic acid ethyl ester
  参考文献：
  名称：

  含四唑啉酮和1,2,4-三唑的二杂环化合物的设计与合成

  摘要：

  1-（4-氯苯基）-4-{[5-（烷硫基）-4-苯基-4 H -1,2,4-三唑-3-基]甲基} -1,4-二氢-的新系列合成了5 H-四唑-5-酮6a-y，收率良好至优异，并通过1 H nmr，13 C nmr，ms和元素分析鉴定了它们的结构。测定化合物6j的X射线晶体学表明，在堆积相互作用中存在强的分子间氢键。生物测定结果表明，化合物6k在250 mg.L -1的剂量下具有良好的对朱砂T的杀虫活性。。据我们所知，这是关于四唑啉酮衍生物的杀虫活性的首次报道。

  DOI：

  10.1002/jhet.5570440433

文献信息

• [EN] NOVEL TETRAZOLONE DERIVATIVES<br/>[FR] NOUVEAUX DÉRIVÉS TÉTRAZOLONE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2014198592A1

  公开（公告）日：2014-12-18

  The invention relates to a compound of formula (I), wherein R1 and R2 are defined as in the description and in the claims. The compound of formula (I) can be used as a medicament.

  该发明涉及一种化合物，其化学式为（I），其中R1和R2如描述和索赔中所定义。化合物的化学式（I）可用作药物。
• NOVEL TETRAZOLONE DERIVATIVES
  申请人：Hoffmann-La Roche Inc.

  公开号：US20160083357A1

  公开（公告）日：2016-03-24

  The invention relates to a compound of formula (I) wherein R 1 and R 2 are defined as in the description and in the claims. The compound of formula (I) can be used as a medicament.

  本发明涉及一种化合物，其化学式为（I），其中R1和R2如说明书和权利要求书中所定义。该化合物可以用作药物。
• TETRAZOLONE DERIVATIVES
  申请人：F. Hoffmann-La Roche AG

  公开号：EP3008055B1

  公开（公告）日：2017-07-19
• Discovery of a new insecticide lead by optimizing a target-diverse scaffold: Tetrazolinone derivatives
  作者：Yan-Ping Luo、Guang-Fu Yang

  DOI：10.1016/j.bmc.2006.12.002

  日期：2007.2

  In order to discover lead compounds with novel action mechanism, a series of tetrazolinone derivatives bearing structurally diverse substituents, 1-aryl-4-substituted-1,4-di-hydro-5H-tetrazol-5-ones 2, 1-((5-(alkylthio)-1,3,4-oxadiazol-2-yl)methyl)-4-(substituted)- phenyl-1H-tetrazol-5(4H)-ones 5, and 1-((5-(alkylthio)-1,3,4-thiadiazol-2-yl)methyl)-4-(substituted)phenyl-1H-tetrazol5(4H)-ones 7, were designed and synthesized in good yields by a multiple-step synthetic procedure. The results of greenhouse in vivo test indicated that all the target compounds did not displayed herbicidal activity, however, some of them exhibited excellent in vivo insecticidal activity against Tetranychus cinnabarinus at the concentration of 250 mg L-1. To our knowledge, this is the first report about the insecticidal activity of tetrazolinone derivatives, which indicated that the tetrazolinone scaffold could be identified as a novel insecticidal lead structure. The present work demonstrated that optimizing a target-diverse scaffold is an effective way to discover new lead compounds with new action mechanism or biological activity. (c) 2006 Elsevier Ltd. All rights reserved.
• Design and synthesis of diheterocyclic compounds containing tetrazolinone and 1,2,4-triazole
  作者：Yan-Ping Luo、Long Lin、Guang-Fu Yang

  DOI：10.1002/jhet.5570440433

  日期：2007.7

  Determining the X-ray crystallography of compound 6j indicated that there were strong intermolecular hydrogen bonds in the stacking interactions. The bioassay results showed that compound 6k exhibited good insecticidal activities against T cinnabarinus at the dosage of 250 mg.L−1. To our knowledge, this is the first report about the insecticidal activity of tetrazolinone derivatives.

  1-（4-氯苯基）-4-[5-（烷硫基）-4-苯基-4 H -1,2,4-三唑-3-基]甲基} -1,4-二氢-的新系列合成了5 H-四唑-5-酮6a-y，收率良好至优异，并通过1 H nmr，13 C nmr，ms和元素分析鉴定了它们的结构。测定化合物6j的X射线晶体学表明，在堆积相互作用中存在强的分子间氢键。生物测定结果表明，化合物6k在250 mg.L -1的剂量下具有良好的对朱砂T的杀虫活性。。据我们所知，这是关于四唑啉酮衍生物的杀虫活性的首次报道。