1-[2-(diethylamino)ethyl]-3-phenylquinoxalin-2(1H)-one | 860672-31-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 1-[2-(diethylamino)ethyl]-3-phenylquinoxalin-2(1H)-one
• 英文别名: 1-(2-diethylamino-ethyl)-3-phenyl-1H-quinoxalin-2-one；1-(2-Diaethylamino-aethyl)-3-phenyl-1H-chinoxalin-2-on；1-[2-(Diethylamino)ethyl]-3-phenyl-2(1H)-quinoxalinone；1-[2-(diethylamino)ethyl]-3-phenylquinoxalin-2-one
• CAS: 860672-31-7
• 化学式: C₂₀H₂₃N₃O
• 分子量: 321.422
• InChiKey: JLIBLRLIARRTQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  35.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[2-(diethylamino)ethyl]-3-phenylquinoxalin-2(1H)-one 在 甲醇 、 铂 作用下， 生成 1-(2-diethylamino-ethyl)-3-phenyl-3,4-dihydro-1H-quinoxalin-2-one
  参考文献：
  名称：

  杂环系列中的药用化学研究。三，信息。喹喔啉系列的季化合物

  摘要：

  根据我们的研究，1-（β-二乙氨基-乙基）-3-苯基-喹喔啉鎓-氯化物-盐酸盐（化合物1）呈现出有趣的药理特性（洋地黄类对离体青蛙心脏的作用）。因此，已经合成了许多相似的喹喔啉鎓化合物，并且以各种方式阐明了它们的结构。

  DOI：

  10.1002/hlca.19520350716
• 作为产物：
  描述：

  N-苯基乙醇胺 在 氯化亚砜 、 sodium dithionite 、 2,2,6,6-四甲基哌啶氧化物 、 硫酸 、 叔丁基二甲基氯硅烷 、 三乙胺 、 N,N-二甲基甲酰胺 、 sodium iodide 、 sodium nitrite 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丙酮 、 甲苯 、 乙腈 为溶剂， 反应 73.0h， 生成 1-[2-(diethylamino)ethyl]-3-phenylquinoxalin-2(1H)-one
  参考文献：
  名称：

  A diversity-oriented synthesis of caroverine derivatives via TEMPO-promoted aerobic oxidative CN bond formation

  摘要：

  A concise method has been developed for the synthesis of caroverine and its derivatives. The quinoxalinone scaffold of these compounds was constructed via the tandem nitrosation/aerobic oxidative C N bond formation reaction of N-(2-chloroethyl)-2-cyano-N-phenylacetamide, followed by sequential Grignard, Finkelstein and nucleophilic substitutions reactions to give several different derivatives. Herein, we describe the development of this strategy in terms of the optimization of each step as well as the effect of different additives on the individual reactions. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.03.061

文献信息

• Quinoxalin-2-one derivatives, compositions which protect useful plants and comprise these derivatives, and processes for their preparation and their use
  申请人：Schaper Wolfgang

  公开号：US20050256000A1

  公开（公告）日：2005-11-17

  Compounds of the formula (I) and salts thereof in which X is O or S; (Y) n =n substituents Y, n is 0, 1, 2, 3 or 4, R 1 is H, OH, NH 2 , (C 1 -C 4 )-alkylamino, di-[(C 1 -C 4 )-alkyl]amino or optionally substituted (C 1 -C 10 )-alkyl, (C 3 -C 10 )-alkenyl, (C 3 -C 10 )-alkynyl or (C 1 -C 10 )-alkoxy, (C 3 -C 10 )-cycloalkyl, (C 4 -C 10 )-cycloalkenyl, aryl or heterocyclyl, R 2 is H or optionally substituted (C 1 -C 10 )-alkyl, (C 3 -C 10 )-alkenyl, (C 3 -C 10 )-alkynyl, (C 3 -C 10 )-cycloalkyl, (C 4 -C 10 )-cycloalkenyl, aryl or heterocyclyl, where the radicals Y are as defined in claim 1 are suitable for use as safeners for crop plants or useful plants against the phytotoxic actions of agrochemicals such as pesticides in these plants.

  该式(I)的化合物及其盐，其中X为O或S；(Y)n=n取代基Y，n为0、1、2、3或4，R1为H、OH、NH2、(C1-C4)-烷基氨基、二-[(C1-C4)-烷基]氨基或可选择取代的(C1-C10)-烷基、(C3-C10)-烯基、(C3-C10)-炔基或(C1-C10)-烷氧基、(C3-C10)-环烷基、(C4-C10)-环烯基、芳基或杂环烷基，R2为H或可选择取代的(C1-C10)-烷基、(C3-C10)-烯基、(C3-C10)-炔基、(C3-C10)-环烷基、(C4-C10)-环烯基、芳基或杂环烷基，其中所述的基Y如权利要求1所定义的适用于作为作物植物或有用植物的安全剂，用于抵抗这些植物中农药等农药的植物毒性作用。
• QUINOXALIN-2-ONE DERIVATIVES, COMPOSITIONS WHICH PROTECT USEFUL PLANTS AND COMPRISE THESE DERIVATIVES, AND PROCESSES FOR THEIR PREPARATION AND THEIR USE
  申请人：Schaper Wolfgang

  公开号：US20110143939A1

  公开（公告）日：2011-06-16

  Compounds of the formula (I) and salts thereof in which X, R 1 , R 2 , Y and n have the meanings indicated in the description, are suitable for use as safeners for crop plants or useful plants against the phytotoxic actions of agrochemicals such as pesticides in these plants.

  式(I)的化合物及其盐，其中X、R1、R2、Y和n的含义如描述中所示，适用于作为农作物或有用植物的安全剂，以防止农药等农业化学品对这些植物的植物毒性作用。
• A diversity-oriented synthesis of caroverine derivatives via TEMPO-promoted aerobic oxidative CN bond formation
  作者：Yusuke Kobayashi、Yusuke Suzuki、Tokutaro Ogata、Tetsutaro Kimachi、Yoshiji Takemoto

  DOI：10.1016/j.tetlet.2014.03.061

  日期：2014.5

  A concise method has been developed for the synthesis of caroverine and its derivatives. The quinoxalinone scaffold of these compounds was constructed via the tandem nitrosation/aerobic oxidative C N bond formation reaction of N-(2-chloroethyl)-2-cyano-N-phenylacetamide, followed by sequential Grignard, Finkelstein and nucleophilic substitutions reactions to give several different derivatives. Herein, we describe the development of this strategy in terms of the optimization of each step as well as the effect of different additives on the individual reactions. (C) 2014 Elsevier Ltd. All rights reserved.
• Heilmittelchemische Studien in der heterocyclischen Reihe. III. Mitteilung. Quaternäre Verbindungen der Chinoxalinreihe
  作者：J. Druey、A. Hüni

  DOI：10.1002/hlca.19520350716

  日期：1952.12.1

  1 - (β - Diethylamino - ethyl) - 3 - phenyl - quinoxalinium - chloride - hydrochloride (compound 1) presents, according to our investigations, interesting pharmacological properties (digitalis like action on the isolated frog heart). A number of similar quinoxalinium-compounds has therefore been synthesized and their structure elucidated in various ways.

  根据我们的研究，1-（β-二乙氨基-乙基）-3-苯基-喹喔啉鎓-氯化物-盐酸盐（化合物1）呈现出有趣的药理特性（洋地黄类对离体青蛙心脏的作用）。因此，已经合成了许多相似的喹喔啉鎓化合物，并且以各种方式阐明了它们的结构。