4-chloro-2-dimethylamino-6-oxo-6H-1,3-oxazine-5-carbonitrile | 132164-86-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-chloro-2-dimethylamino-6-oxo-6H-1,3-oxazine-5-carbonitrile
• 英文别名: 4-chloro-5-cyano-2-dimethylamino-6-oxo-6H-1,3-oxazine；4-Chloro-5-cyano-2-dimethylamino-6H-1,3-oxazin-6-one；4-chloro-2-(dimethylamino)-6-oxo-6H-1,3-oxazine-5-carbonitrile；4-chloro-2-(dimethylamino)-6-oxo-1,3-oxazine-5-carbonitrile
• CAS: 132164-86-4
• 化学式: C₇H₆ClN₃O₂
• mdl: MFCD00171918
• 分子量: 199.597
• InChiKey: VDCBXTAMVFEOSK-UHFFFAOYSA-N

物化性质

• 熔点：
  167-168 °C
• 沸点：
  237.0±50.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  65.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-chloro-2-dimethylamino-6-oxo-6H-1,3-oxazine-5-carbonitrile 在 叠氮基三甲基硅烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以77.7%的产率得到4-azido-2-dimethylamino-6-oxo-6H-1,3-oxazin-5-carbonitrile
  参考文献：
  名称：

  新型叠氮化物衍生物的合成与化学反应

  摘要：

  摘要 由 4-氯化合物得到的 4-Azido-2-dialkylamino-6-oxo-6H-1,3-oxazin-5-carbonitriles 用于合成 N-(1,3-oxazin-4-yl )亚氨基膦。然后将三苯基亚氨基正膦水解成杂环胺。

  DOI：

  10.1080/00397919408010571
• 作为产物：
  描述：

  二氯亚甲基二甲基氯化铵 、 potassium salt of ethyl dicyanoacetate 以 氯仿 为溶剂， 反应 24.0h， 以72%的产率得到4-chloro-2-dimethylamino-6-oxo-6H-1,3-oxazine-5-carbonitrile
  参考文献：
  名称：

  Synthesis of 4-Chloro-5-cyano-2-dimethylamino-6H-1,3-oxazin-6-one from the Salts of Alkyl Dicyanoacetates and Some of Its Reactions

  摘要：

  二氰基乙酸烷基酯和3-氨基-3-氯-2-氰基丙烯酸甲酯的盐在氯仿中与N-(二氯亚甲基)二甲基氯化铵反应，得到4-氯-5-氰基-2-二甲基-氨基-6H,3-恶嗪-6-一。该化合物的氯原子可以很容易地被醇或胺取代，且产率良好。

  DOI：

  10.1055/s-1990-27065

文献信息

• Synthesis of 3-Amino-6-dimethylamino-4-oxopyrazolo[3,4-<i>d</i>] [1,3]oxazine Derivatives
  作者：Richard Neidlein、Zhihua Sui

  DOI：10.1055/s-1991-26538

  日期：——

  3-Amino-1-aryl-6-dimethylamino-4-oxo-1,4-dihydropyrazolo[3,4-d][1,3] oxazines 4a-7a and 3-amino-2-aryl-6-dimethylamino-4-oxo-2,4-dihydropyrazolo [3,4-d][1,3]oxazines 4b-6b were synthesized from 4-chloro-5-cyano-2-dimethylamino-6-oxo-6H-1,3-oxazine 2 and arylhydrazines in good yields. The substituent effect of the arylhydrazines on the yields of products was clearly observed.

  3-氨基-1-芳基-6-二甲氨基-4-氧-1,4-二氢吡唑并[3,4-d][1,3]氧氮杂环庚烷 4a-7a 及 3-氨基-2-芳基-6-二甲氨基-4-氧-2,4-二氢吡唑并[3,4-d][1,3]氧氮杂环庚烷 4b-6b 从 4-氯-5-腈基-2-二甲氨基-6-氧-6H-1,3-氧氮杂环庚烷 2 与芳基酰肼中以良好产率合成得到。可明显观察到芳基酰肼的取代基效应对产物产率的影响。
• Synthesis of Some 4-Chloro-5-cyano-2-dialkylamino-6<i>H</i>-1,3-oxazin-6-ones and their Reactions with Trialkyl Phosphites to Give Dialkyl (5-Cyano-2-dialkylamino-6-oxo-6<i>H</i>-1,3-oxazin-4-yl)phosphonates
  作者：Richard Neidlein、Peter Meffert、Zhihua Sui

  DOI：10.1055/s-1992-26129

  日期：——

  The reaction of the salts of alkyl dicyanoacetates and N-(dichloromethylene) dialkylammonium chlorides in chloroform leads to 4-chloro-5-cyano-2-dialkylamino-6H -1,3-oxazin-6-ones. The chloro atom of these compounds can be easily substituted in a Michaelis-Arbuzov reaction with trialkyl phosphites, giving dialkyl (5-cyano-2-dialkylamino-6-oxo-6-H-1,3-oxazin-4-yl)phosphonates in good yields.

  二氰基乙酸烷基酯和 N-（二氯亚甲基）二烷基氯化铵的盐类在氯仿中反应生成 4-氯-5-氰基-2-二烷基氨基-6H-1,3-恶嗪-6-酮。这些化合物的氯原子可以很容易地与三烷基亚磷酸发生迈克尔-阿尔布佐夫反应，从而以良好的收率得到二烷基（5-氰基-2-二烷基氨基-6-氧代-6-H-1,3-恶嗪-4-基）膦酸盐。
• Syntheses of New Heterocycles Starting from Dicyanoacetates
  作者：Richard Neidlein、Peter Meffert

  DOI：10.3987/com-94-s5

  日期：——

  The reactions of 4-chloro-2-dialkylamino-6-oxo-6H-1,3-oxazine-5-carbonitriles (3) with C-, N- and S-nucleophiles are reported. The chloro atom can also be substituted in a Michaelis-Arbuzov reaction giving the corresponding 1,3-oxazinyl phosphinates and phosphinoxides.
• NEIDLEIN, RICHARD;SUI, ZHIHUA, SYNTHESIS (BRD),(1990) N0, C. 959-961
  作者：NEIDLEIN, RICHARD、SUI, ZHIHUA

  DOI：——

  日期：——
• Synthesis of 4-Chloro-5-cyano-2-dimethylamino-6<i>H</i>-1,3-oxazin-6-one from the Salts of Alkyl Dicyanoacetates and Some of Its Reactions
  作者：Richard Neidlein、Zhihua Sui

  DOI：10.1055/s-1990-27065

  日期：——

  The salts of alkyl dicyanoacetates and methyl 3-amino-3-chloro-2-cyanoacrylate react in chloroform with N-(dichloromethylene)dimethylammonium chloride to give 4-chloro-5-cyano-2-dimethyl- amino-6H,3-oxazin-6-one. The chloro atom of this compound can be easily substituted by alcohols or amines in good yield.

  二氰基乙酸烷基酯和3-氨基-3-氯-2-氰基丙烯酸甲酯的盐在氯仿中与N-(二氯亚甲基)二甲基氯化铵反应，得到4-氯-5-氰基-2-二甲基-氨基-6H,3-恶嗪-6-一。该化合物的氯原子可以很容易地被醇或胺取代，且产率良好。