5-Chloro-2-methoxy-benzoyl isocyanate | 82250-54-2

• 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: 5-Chloro-2-methoxy-benzoyl isocyanate
• 英文别名: 5-Chloro-2-methoxybenzoyl isocyanate；5-chloro-2-methoxybenzoyl isocyanate
• CAS: 82250-54-2
• 化学式: C₉H₆ClNO₃
• 分子量: 211.605
• InChiKey: KDSOROKFRJVERH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  55.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-Chloro-2-methoxy-benzoyl isocyanate 、 (1S,5R)-8-Methyl-8-azabicyclo[3.2.1]octan-3-amine 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 生成 1-(5-Chloro-2-methoxy-benzoyl)-3-((1R,3R,5S)-8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-urea
  参考文献：
  名称：

  Novel antagonists of the 5-HT3 receptor. Synthesis and structure-activity relationships of (2-alkoxybenzoyl)ureas

  摘要：

  A series of benzoylureas derived from bicycle amines were prepared and evaluated for 5-HT3 antagonist activity on the rat isolated vagus nerve. From among these compounds, those analogues which were ortho substituted by an alkoxy group on the benzoyl function were shown to be potent 5-HT3 antagonists with similar or greater potency than the standard agent ondansetron. NMR and X-ray crystallography studies showed these o-alkoxy compounds to exist as a planar, hydrogen-bonded, tricyclic ring system. In molecular modeling studies on endo-N-[[(8-methyl-8-azabicyclo [3.2.1]octan-3-yl)amino]carbonyl]-2-(cyclopropylmethoxy)benzamide (30) the central hydrogen-bonded ring was able to mimic an aromatic ring present in previously reported 5-HT3 antagonists.

  DOI：

  10.1021/jm00087a003
• 作为产物：
  描述：

  草酰氯 、 5-chloro-2-methoxybenzamide 以 1,2-二氯乙烷 为溶剂， 反应 5.0h， 生成 5-Chloro-2-methoxy-benzoyl isocyanate
  参考文献：
  名称：

  具有杀虫和抗真菌活性的新型农药的研究：苯甲酰基嘧啶基脲衍生物的设计、合成和 SAR 研究

  摘要：

  为了寻找具有杀虫和抗真菌活性的农药，设计并合成了一系列新型苯甲酰嘧啶基脲衍生物。所有目标化合物均通过 1 H-NMR 光谱和 HRMS 进行鉴定。评估了这些化合物的杀虫和抗真菌活性，并清楚而全面地说明了构效关系 (SAR)。化合物 7 对斑马鱼的毒性较低（LC50 = 378.387 µg mL − 1），浓度为 0.25 µg mL − 1 时对蚊子（淡色库蚊）有 100% 的抑制作用。化合物19和25均表现出广谱杀菌活性（对13种植物病原真菌的抑制活性> 50%），优于商业农药嘧霉胺（对8种植物病原真菌的抑制活性> 50%）。此外，

  DOI：

  10.3390/molecules23092203

文献信息

• Sulfonylharnstoffe, Verfahren zu ihrer Herstellung, pharmazeutische Präparate auf Basis dieser Verbindungen und ihre Verwendung
  申请人：HOECHST AKTIENGESELLSCHAFT

  公开号：EP0047496A1

  公开（公告）日：1982-03-17

  Sulfonylharnstoffe der Formel worin R1, R2, R3, X und Y die angegebenen Bedeutungen haben, sowie deren physiologisch verträglichen Salze, ihre Verwendung bei der Behandlung des Diabetes und pharmazeutische Präparate auf Basis dieser Verbindungen.

  式中 R1、R2、R3、X 和 Y 具有上述含义的磺脲类化合物及其生理耐受盐、它们在治疗糖尿病中的用途以及基于这些化合物的药物制剂。
• Investigation of Novel Pesticides with Insecticidal and Antifungal Activities: Design, Synthesis and SAR Studies of Benzoylpyrimidinylurea Derivatives
  作者：Peiqi Chen、Xiangmin Song、Yongmei Fan、Weihao Kong、Hao Zhang、Ranfeng Sun

  DOI：10.3390/molecules23092203

  日期：——

  mL−1. Both compounds 19 and 25 exhibited broad-spectrum fungicidal activity (>50% inhibitory activities against 13 phytopathogenic fungi), which were better than those of the commercial pesticide pyrimethanil (>50% inhibitory activities against eight phytopathogenic fungi). Furthermore, compounds 19 and 25 exhibited protective activity against Sclerotinia sclerotiorum on leaves of Brassica oleracea L

  为了寻找具有杀虫和抗真菌活性的农药，设计并合成了一系列新型苯甲酰嘧啶基脲衍生物。所有目标化合物均通过 1 H-NMR 光谱和 HRMS 进行鉴定。评估了这些化合物的杀虫和抗真菌活性，并清楚而全面地说明了构效关系 (SAR)。化合物 7 对斑马鱼的毒性较低（LC50 = 378.387 µg mL − 1），浓度为 0.25 µg mL − 1 时对蚊子（淡色库蚊）有 100% 的抑制作用。化合物19和25均表现出广谱杀菌活性（对13种植物病原真菌的抑制活性> 50%），优于商业农药嘧霉胺（对8种植物病原真菌的抑制活性> 50%）。此外，
• Novel antagonists of the 5-HT3 receptor. Synthesis and structure-activity relationships of (2-alkoxybenzoyl)ureas
  作者：Gerald Bradley、Terence J. Ward、Janet C. White、James Coleman、Ann Taylor、Keith F. Rhodes

  DOI：10.1021/jm00087a003

  日期：1992.5

  A series of benzoylureas derived from bicycle amines were prepared and evaluated for 5-HT3 antagonist activity on the rat isolated vagus nerve. From among these compounds, those analogues which were ortho substituted by an alkoxy group on the benzoyl function were shown to be potent 5-HT3 antagonists with similar or greater potency than the standard agent ondansetron. NMR and X-ray crystallography studies showed these o-alkoxy compounds to exist as a planar, hydrogen-bonded, tricyclic ring system. In molecular modeling studies on endo-N-[[(8-methyl-8-azabicyclo [3.2.1]octan-3-yl)amino]carbonyl]-2-(cyclopropylmethoxy)benzamide (30) the central hydrogen-bonded ring was able to mimic an aromatic ring present in previously reported 5-HT3 antagonists.