N-(6-methoxy-[8]quinolyl)-glycine-nitrile | 858279-55-7

• 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: N-(6-methoxy-[8]quinolyl)-glycine-nitrile
• 英文别名: N-(6-Methoxy-[8]chinolyl)-glycin-nitril；2-[(6-Methoxyquinolin-8-yl)amino]acetonitrile
• CAS: 858279-55-7
• 化学式: C₁₂H₁₁N₃O
• 分子量: 213.239
• InChiKey: QTOAUHLAXJORPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  57.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(6-methoxy-[8]quinolyl)-glycine-nitrile 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 N¹-(6-methoxyquinolin-8-yl)ethan-1,2-diamine
  参考文献：
  名称：

  8-aminoquinolines as anticoccidials - part III

  摘要：

  Analogues of the antimalarial pentaquine, 1, in which the nature of the side-chain on the 8-amino position was varied, were prepared and evaluated for anticoccidial activity both in vitro and in vivo. Specifically, both the inter-nitrogen distance and the nature of the terminal amino group were investigated. Novel analogues of equal or improved efficacy in vitro and in vivo to pentaquine were discovered. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00393-5
• 作为产物：
  描述：

  2-硝基-4-甲氧基苯胺 在 镍 arsenic(V) oxide 、 磷酸 、 氢气 、 三乙胺 作用下， 以 乙腈 为溶剂， 20.0~100.0 ℃ 、344.74 kPa 条件下， 反应 2.0h， 生成 N-(6-methoxy-[8]quinolyl)-glycine-nitrile
  参考文献：
  名称：

  8-aminoquinolines as anticoccidials - part III

  摘要：

  Analogues of the antimalarial pentaquine, 1, in which the nature of the side-chain on the 8-amino position was varied, were prepared and evaluated for anticoccidial activity both in vitro and in vivo. Specifically, both the inter-nitrogen distance and the nature of the terminal amino group were investigated. Novel analogues of equal or improved efficacy in vitro and in vivo to pentaquine were discovered. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00393-5

文献信息

• Cyclic amidine
  申请人：CIBA PHARM PROD INC

  公开号：US02252721A1

  公开（公告）日：1941-08-19

  528,915. Amidines. SOC. OF CHEMICAL INDUSTRY IN BASLE. May 8, 1939, Nos. 13684 and 13685. Convention dates, May 11, 1938, and April 15, 1939. [Class 2 (iii)] Amidines are prepared by reacting an aliphatic amino acid having an aromatic or heterocyclic residue as a substituent at the nitrogen atom, or an imido-ether, imido halide, or thioamide of such an acid, with ammonia or a primary or secondary aliphatic, araliphatic, or heterocyclic amine. The compounds comprise the structure where A is an amino alkyl residue containing an aromatic or heterocyclic residue as a substituent on the nitrogen atom. The products may be open chain or cyclic compounds. In the latter case both amidine nitrogen atoms are united by an alkylene chain as in an imidazoline or tetrahydropyrimidine ring. Amines mentioned include saturated or unsaturated alkylamihes, alkylene diamines, aralkyl amines, heterocyclic amines such as aminopyridines, aminoquinolines or aminobenzthiazoles, and cyclicamines such as piperidine. In examples: (1) phenylaminoacetimido-ethyl ether hydrochloride is 'treated with ammonia in alcohol solution to give phenylaminoacetamidine. The phenyl group may be substituted for instance by an alkyl-, alkoxy-, oxy-, aryloxy-, amino-, nitro-, or carboxyl-group. Similarly there may be obtained α-phenylamino-n-caprylic acid amidine, the γ-phenylamino-butyramidine, or the #-phenylamino-n-caproic acid amidine; (2) phenylaminoacetimidoethyl-ether is reacted with piperidine in alcohol solution to give phenylaminoacetpiperidine. Instead of the ethyl ether, the propyl ether may be used. (3) Phenylaminoacetimidoethyl-ether is reacted with #-phenylethylamine in alcoholic solution to give phenylaminoacet-#-phenylethylamidine. (4) Phenylaminoacetimidoethyl-ether hydrochloride is reacted with ethylenediamine in alcohol solution to give 2-(phenylaminomethyl)- imidazoline hydrochloride. Instead of ethylenediamine there may be used 1:2 or 1:3-propylenediamine to give a corresponding product: (5) Phenylaminothioacetamide and ethylenediamine are heated together in an oil bath to give phenylamino-methyl-tetrahydropyrimidine. In similar manner a number of similar compounds may be obtained which are specified. The imino-ethers which are used as parent materials for the process of the invention may be obtained easily when the condensation of the alcohol with the nitrile in the presence of an acid such as hydrochloric acid is conducted in chloroform solution. 6-Methoxy-quinolyl-8-aminoacetonitrile and 6-methoxy-quinolyl - 8 - amino - y - butyronitrile may be prepared by the reaction of 6-methoxy- 8-aminoquinoline with chloroacetonitrile and #-chloro-butyronitrile respectively. 4-Methoxyphenylaminoacetonitrile may be obtained from para-anisidine-formaldehyde bisulphate and potassium cyanide in aqueous solution.

  528,915. 脒类化合物。巴塞尔化学工业公司。1939年5月8日，编号13684和13685。会议日期分别为1938年5月11日和1939年4月15日。[第2类（iii）] 通过将具有芳香或杂环残基的脂肪族氨基酸或该酸的咪唑醚，咪唑卤化物或硫酰胺与氨或一次或二次脂肪族，芳基脂肪族或杂环胺反应来制备脒类化合物。这些化合物包括结构式，其中A是含有氮原子上的芳香或杂环残基的氨基烷基残基。产物可以是开链或环状化合物。在后一种情况下，两个脒基氮原子由烷基链连接，如在咪唑啉或四氢嘧啶环中。所提到的胺包括饱和或不饱和的烷基胺，烷基二胺，芳基烷基胺，如氨基吡啶，氨基喹啉或氨基苯并噻唑，以及环胺，如哌啶。在实例中：（1）苯胺乙酰亚胺乙醚盐酸盐在醇溶液中与氨反应，得到苯胺乙酰脒。苯基可以被置换，例如，通过烷基，烷氧基，氧基，芳氧基，氨基，硝基或羧基。类似地，可以得到α-苯胺基-n-癸酸脒，γ-苯胺基-丁酰胺脒或#-苯胺基-n-己酸脒; （2）苯胺乙酰亚胺乙醚在醇溶液中与哌啶反应，得到苯胺乙酰哌啶。可以使用丙醚代替乙醚; （3）苯胺乙酰亚胺乙醚在醇溶液中与#-苯乙胺反应，得到苯胺乙酰-#-苯乙胺脒; （4）苯胺乙酰亚胺乙醚盐酸盐在醇溶液中与乙二胺反应，得到2-（苯氨甲基）-咪唑啉盐酸盐。可以使用1:2或1:3-丙二胺代替乙二胺以得到相应的产物; （5）苯胺基硫酰胺和乙二胺在油浴中加热反应，得到苯胺基甲基四氢嘧啶。以类似的方式可以得到一些类似的化合物，这些化合物已经被指定。用作本发明工艺的亚胺醚可以在氯仿溶液中醇与腈的缩合反应中在氢氯酸等酸的存在下轻松获得。6-甲氧基喹啉-8-氨基乙腈和6-甲氧基喹啉-8-氨基-γ-丁腈可以通过6-甲氧基-8-氨基喹啉与氯乙腈和#-氯丁腈的反应分别制备。4-甲氧基苯胺基乙腈可以从对甲氧基苯胺-甲醛双硫酸盐和氰化钾在水溶液中获得。
• DE701322
  申请人：——

  公开号：——

  公开（公告）日：——