6-chloro-9-(3,4,5-trimethoxy-phenyl)-3H-furo[3,4-b]quinolin-1-one | 867070-50-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6-chloro-9-(3,4,5-trimethoxy-phenyl)-3H-furo[3,4-b]quinolin-1-one
• 英文别名: 6-chloro-9-(3,4,5-trimethoxyphenyl)-3H-furo[3,4-b]quinolin-1-one
• CAS: 867070-50-6
• 化学式: C₂₀H₁₆ClNO₅
• 分子量: 385.804
• InChiKey: LAUYBTZDGZLOER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-chloro-9-(3,4,5-trimethoxy-phenyl)-3H-furo[3,4-b]quinolin-1-one 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 反应 3.0h， 以25 mg的产率得到6-chloro-9-(3,4,5-trimethoxyphenyl)-4,9-dihydrofuro[3,4-b]quinolin-1(3H)-one
  参考文献：
  名称：

  Insecticidal heterolignans—Tubuline polymerization inhibitors with activity against chewing pests

  摘要：

  Starting from natural product podophyllotoxin 1 substituted heterolignans were identified with promising insecticidal in vivo activity. The impact of substitution in each segment of the core structure was investigated in a detailed SAR study, and variation of substituents in both aromatic moieties afforded derivatives 5 and 43 with broad insecticidal activity against lepidopteran and coleopteran species. In vitro measurements supported by modeling studies indicate that heterolignans 3-134 act as tubuline polymerization inhibitors interacting with the colchicine-binding site. Insect specific structure-activity effects were observed showing that the insecticidal SAR described herein differs from reported cytotoxicity studies. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.01.042
• 作为产物：
  描述：

  4-羟基-2(5H)-呋喃酮 、 (2-amino-4-chloro-phenyl)-(3,4,5-trimethoxy-phenyl)-methanone 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以91%的产率得到6-chloro-9-(3,4,5-trimethoxy-phenyl)-3H-furo[3,4-b]quinolin-1-one
  参考文献：
  名称：

  [DE] ANNELLIERTE CHINOLINDERIVATE ALS PESTIZIDE
  [EN] ANNELATED QUINOLINE DERIVATIVES AS PESTICIDE
  [FR] DERIVES DE QUINOLEINE ANNELES COMME PESTICIDES

  摘要：

  本发明申请涉及使用式（I）的喹啉衍生物，其中虚线结合代表单键或双键，并且取代基具有描述中所指定的含义，作为植物处理剂，特别用于对抗动物害虫；基于已知和新的螺环喹啉衍生物的植物处理剂和新的喹啉衍生物。

  公开号：

  WO2005097802A1

文献信息

• [DE] ANNELLIERTE CHINOLINDERIVATE ALS PESTIZIDE<br/>[EN] ANNELATED QUINOLINE DERIVATIVES AS PESTICIDE<br/>[FR] DERIVES DE QUINOLEINE ANNELES COMME PESTICIDES
  申请人：BAYER CROPSCIENCE AG

  公开号：WO2005097802A1

  公开（公告）日：2005-10-20

  Die vorliegende Anmeldung einer Erfindung betrifft die Verwendung von Chinolinderivaten der Formel (I) in welcher die gestrichelte Bindung für eine Einfach- oder Doppelbindung sthet und die Substiutenten die in der Beschreibung angegebene Bedeutung haben, als Pflanzenbehandlungsmittel, insbesondere zur Bekämpfung von tierischen Schädlingen; Pflanzenbehandlungsmittel auf Basis von bekannten und neuen annellierten Chinolinderivaten und neue Chinolinderivate.

  本发明申请涉及使用式（I）的喹啉衍生物，其中虚线结合代表单键或双键，并且取代基具有描述中所指定的含义，作为植物处理剂，特别用于对抗动物害虫；基于已知和新的螺环喹啉衍生物的植物处理剂和新的喹啉衍生物。
• Annelated Quinoline Derivatives As Pesticide
  申请人：Velten Robert

  公开号：US20080113994A1

  公开（公告）日：2008-05-15

  The present filing of an invention relates to the use of quinoline derivatives of the formula in which the dashed bond is a single or double bond and the substituents have the definition given in the disclosure, as crop treatment compositions, particularly for controlling animal pests; to crop treatment compositions based on known and new annulated quinoline derivatives; and to new quinoline derivatives.

  本发明涉及使用式中虚线键为单键或双键，且取代基具有所述披露的定义的喹啉衍生物作为作物处理组合物，特别用于控制动物害虫；基于已知和新的环化喹啉衍生物的作物处理组合物；以及新的喹啉衍生物。
• Insecticidal heterolignans—Tubuline polymerization inhibitors with activity against chewing pests
  作者：Jens Frackenpohl、Isabelle Adelt、Horst Antonicek、Christian Arnold、Patricia Behrmann、Nicole Blaha、Jutta Böhmer、Oliver Gutbrod、Roman Hanke、Sabine Hohmann、Marc van Houtdreve、Peter Lösel、Olga Malsam、Martin Melchers、Valentina Neufert、Elisabeth Peschel、Udo Reckmann、Thomas Schenke、Hans-Peter Thiesen、Robert Velten、Kathrin Vogelsang、Hans-Christoph Weiss

  DOI：10.1016/j.bmc.2009.01.042

  日期：2009.6

  Starting from natural product podophyllotoxin 1 substituted heterolignans were identified with promising insecticidal in vivo activity. The impact of substitution in each segment of the core structure was investigated in a detailed SAR study, and variation of substituents in both aromatic moieties afforded derivatives 5 and 43 with broad insecticidal activity against lepidopteran and coleopteran species. In vitro measurements supported by modeling studies indicate that heterolignans 3-134 act as tubuline polymerization inhibitors interacting with the colchicine-binding site. Insect specific structure-activity effects were observed showing that the insecticidal SAR described herein differs from reported cytotoxicity studies. (C) 2009 Elsevier Ltd. All rights reserved.