2-Chlor-5-nitro-benzhydroxamoylchlorid | 129144-22-5

• 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: 2-Chlor-5-nitro-benzhydroxamoylchlorid
• CAS: 129144-22-5
• 化学式: C₇H₄Cl₂N₂O₃
• 分子量: 235.026
• InChiKey: JRMPJFJMJDZURY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.73
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-Chlor-5-nitro-benzhydroxamoylchlorid 在 铁粉 、 氯化铵 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 3-(5-amino-2-chloro-phenyl)-5-methyl-4H-isooxazole-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  Discovery of Novel N-Isoxazolinylphenyltriazinones as Promising Protoporphyrinogen IX Oxidase Inhibitors

  摘要：

  Protoporphyrinogen oxidase (PPO, EC 1.3.3.4) is a promising target for herbicide discovery. Search for new compounds with novel chemotypes is a key objective for agrochemists. Here, we describe the discovery and systematic SAR-based structure optimization of novel N-isoxazolinylphenyltriazinones 5-9 as PPO inhibitors. The in vivo herbicidal activity and in vitro Nicotiana tabacum PPO (NtPPO) inhibitory activity were explored in detail. A number of the new synthetic compounds displayed strong PPO inhibitory activity with K-i values in the nanomolar range. Some compounds exhibited excellent and broad-spectrum weed control at the rate of 9.375-37.5 g ai/ha by postemergence application and showed improved monocotyledonous weed control compared to saflufenacil. Most promisingly, ethyl 3-(2-chloro-5-(3,5-dimethyl--2,6-dioxo-4-thioxo-1,3,5-triazinan-1-yl)-4-fluorophenyl)-5-methyl-4,5-dihydroisoxazole-5-carboxylate, 5a, with a K-i value of 4.9 nM, displayed over 2- and 6-fold higher potency than saflufenacil (K-i = 10 nM) and trifludimoxazin (K-i = 31 nM), respectively. Moreover, 5a showed excellent and broad-spectrum weed control against 32 kinds of weeds at 37.5-75 g ai/ha. Rice exhibited relative tolerance to 5a at 150 g ai/ha by postemergence application, indicating that Sa could be a potential herbicide candidate for weed control in paddy fields.

  DOI：

  10.1021/acs.jafc.9b04844
• 作为产物：
  描述：

  2-氯-5-硝基苯甲醛 在 N-氯代丁二酰亚胺 、 盐酸羟胺 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-Chlor-5-nitro-benzhydroxamoylchlorid
  参考文献：
  名称：

  Discovery of Novel N-Isoxazolinylphenyltriazinones as Promising Protoporphyrinogen IX Oxidase Inhibitors

  摘要：

  Protoporphyrinogen oxidase (PPO, EC 1.3.3.4) is a promising target for herbicide discovery. Search for new compounds with novel chemotypes is a key objective for agrochemists. Here, we describe the discovery and systematic SAR-based structure optimization of novel N-isoxazolinylphenyltriazinones 5-9 as PPO inhibitors. The in vivo herbicidal activity and in vitro Nicotiana tabacum PPO (NtPPO) inhibitory activity were explored in detail. A number of the new synthetic compounds displayed strong PPO inhibitory activity with K-i values in the nanomolar range. Some compounds exhibited excellent and broad-spectrum weed control at the rate of 9.375-37.5 g ai/ha by postemergence application and showed improved monocotyledonous weed control compared to saflufenacil. Most promisingly, ethyl 3-(2-chloro-5-(3,5-dimethyl--2,6-dioxo-4-thioxo-1,3,5-triazinan-1-yl)-4-fluorophenyl)-5-methyl-4,5-dihydroisoxazole-5-carboxylate, 5a, with a K-i value of 4.9 nM, displayed over 2- and 6-fold higher potency than saflufenacil (K-i = 10 nM) and trifludimoxazin (K-i = 31 nM), respectively. Moreover, 5a showed excellent and broad-spectrum weed control against 32 kinds of weeds at 37.5-75 g ai/ha. Rice exhibited relative tolerance to 5a at 150 g ai/ha by postemergence application, indicating that Sa could be a potential herbicide candidate for weed control in paddy fields.

  DOI：

  10.1021/acs.jafc.9b04844

文献信息

• The rapid generation of isothiocyanates in flow
  作者：Marcus Baumann、Ian R Baxendale

  DOI：10.3762/bjoc.9.184

  日期：——

  Isothiocyanates are versatile starting materials for a wide range of chemical reactions. However, their high nucleophilic susceptibility means they are best prepared and used immediately. We report here on a flow platform for the fast and efficient formation of isothiocyanates by the direct conversion of easily prepared chloroximes. To expedite this chemistry a flow insert cartridge containing two immobilised reagents is used to affect the chemical transformation which typically eliminates the requirements for any conventional work-up or purification of the reaction stream.

  异硫氰酸酯是用于各种化学反应的多功能起始物。然而，它们具有高亲核敏感性，意味着最好立即制备和使用。我们在这里报告了一种用于通过直接将易于制备的氯氧胺转化而快速高效形成异硫氰酸酯的流动平台。为了加快这种化学反应，使用了一个含有两种固定试剂的流动插入式卡匣，用于影响化学转化，通常消除了对反应流体的任何传统处理或纯化的要求。
• A Novel Route to 2-Arylquinolines: Reductive Cleavage of 2′-Nitroaryl-∆2-isoxazolines
  作者：Mukul Lal、Prashantha Kamath、Russell Viner、Stephen Smith

  DOI：10.1055/s-0036-1588751

  日期：2017.7

  A novel synthetic route for the synthesis of quinolines starting from Δ2-isoxazolines under reductive conditions is reported. The ­reductive cyclization to quinolines is achieved under both metal and metal-free conditions. The reaction proceeds via an intramolecular N–H···O hydrogen bond intermediate, accelerating the reductive cleavage 1000-fold (DFT calculations) in comparison with non-hydrogen bonded

  报道了一种在还原条件下以 Δ2-异恶唑啉为原料合成喹啉的新合成路线。在金属和无金属条件下均可实现还原环化为喹啉。该反应通过分子内 N-H···O 氢键中间体进行，与非氢键系统相比，还原裂解加速了 1000 倍（DFT 计算）。
• 1120. Derivatives of 6-aminopenicillanic acid. Part VIII. Further analogues of 3-O-chorophenyl-5-methyl-4-isoxazolylpenicillin
  作者：J. C. Hanson、A. A. W. Long、J. H. C. Nayler、E. R. Stove

  DOI：10.1039/jr9650005976

  日期：——
• Kim, Jae Nyoung; Ryu, Eung K., Heterocycles, 1990, vol. 31, # 4, p. 663 - 670
  作者：Kim, Jae Nyoung、Ryu, Eung K.

  DOI：——

  日期：——