2-morpholin-1-ylmethylenemalononitrile | 38238-94-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 2-morpholin-1-ylmethylenemalononitrile
• 英文别名: morpholinomethylenemalonitrile；Morpholinomethylenmalononitril；2-(morpholinomethylene)malononitrile；Morpholinomethylen-malonsaeuredinitril；morpholin-4-ylmethylene-malononitrile；Morpholinomethylenmalodinitril；2-(4-Morpholinylmethylene)malononitrile；2-(morpholin-4-ylmethylidene)propanedinitrile
• CAS: 38238-94-7
• 化学式: C₈H₉N₃O
• mdl: MFCD00170862
• 分子量: 163.179
• InChiKey: SFJZXGXGTRXJJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  60
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-morpholin-1-ylmethylenemalononitrile 在 platinum(IV) oxide 盐酸 、 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、482.63 kPa 条件下， 反应 9.0h， 以32%的产率得到2-morpholin-1-ylmethyl-propane-1,3-diamine trihydrochloride
  参考文献：
  名称：

  Hydrogenation of Imino‐bisnitriles—Synthesis of Novel Triamines

  摘要：

  DOI：

  10.1080/00397910601038970
• 作为产物：
  描述：

  吗啉 、 3-bromoisothiazole-4-carbonitrile 以 乙醇 为溶剂， 反应 24.0h， 以71%的产率得到2-morpholin-1-ylmethylenemalononitrile
  参考文献：
  名称：

  Regioselective hydrodehalogenation of 3,5-dihaloisothiazole-4-carbonitriles: synthesis of 3-haloisothiazole-4-carbonitriles

  摘要：

  3,5-Dibromoisothiazole-4-carbonitrile 1 treated with Zn or In dust (5 equiv) and HCO2H undergoes regioselective hydrodebromination to give 3-bromoisothiazole-4-carbonitrile 3 in 70-74% yield. Similarly, 5-bromo and iodo 3-chloroisothiazole-4-carbonitriles 8 and 9 give 3-chloroisothiazole-4-carbonitrile 4 in 77 and 85% yields, respectively. Also hydrodeamination of 5-amino-3-chloroisothiazole-4-carbonitrile 7 using isoamyl nitrite gives the latter in 95% yield. The dibromoisothiazole 1 reacts with Zn dust in either DCO2D or HCO2D to give 3-bromo-5-deuterioisothiazole-4-carbonitrile 10 in 71 and 58% yields, respectively. The 3-bromoisothiazole 3 reacts with cyclic dialkylamines to give the corresponding 2-(dialkylaminomethylene)-malononitriles and not the expected 3-dialkylaminoisothiazole-4-carbonitriles. Finally, the 3-bromoisothiazole 3 is readily converted into both 3-bromoisothiazole-4-carboxamide 19 and the carboxylic acid 20. All products are fully characterized. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.065

文献信息

• Arynes Double Bond Insertion/Nucleophilic Addition with Vinylogous Amides and Carbodiimides
  作者：Ran Li、Huarong Tang、Haixing Fu、Hailong Ren、Xuemei Wang、Chunrui Wu、Chao Wu、Feng Shi

  DOI：10.1021/jo402754d

  日期：2014.2.7

  some C═X double bonds, leading to benzannulated four-membered rings. The strain of these rings allow for a ready, spontaneous opening to afford o-quinomethide analogues. Subsequent nucleophilic addition re-aromatizes the intermediates to achieve ortho-difunctionalization of arynes. In this report, we describe the aryne insertion into the C═C double bonds of vinylogous amides and the C═N double bonds of

  显示出Arynes插入某些C═X双键中，导致苯环环化的四元环。这些环的应变允许容易地，自发地打开以提供邻喹啉类似物。随后的亲核加成使中间体重新芳构化，以实现芳烃的邻-双官能化。在本报告中，我们描述了芳烃插入乙烯基酰胺的C═C双键和碳二亚胺的C═N双键。将讨论与芳烃单键插入化学的相关性和比较。也将讨论开环步骤的计算研究，以及邻甲基喹啉中间体的性质。
• Ring Transformation Reactions Starting from 6-Imino-6H-1,3-thiazines
  作者：Detlef Briel

  DOI：10.3987/com-03-9852

  日期：——

  Ring transformation reactions of 6-imino-6H-1,3-thiazines (4), 6-imino-6H-1,3-thiazine hydroperchlorates (3), respectively, are initiated under basic conditions by a ring opening of the thiazine nucleous. Two possibilities exist, either intramolecular elimination occurs to give acrylonitriles (5), or addition of a nucleophile (YH) results in the formation of substituted acrylthio-amides (6). The way by which stable products were formed depends on both the functionality of the thiazine, and the reaction conditions. The way 4-->5 produce 1,3-benzoxazines (8), or 1,2,4-dithiazoles (14), respectively. The way 4 --> 6 gives pyrimidinethiones (7), or 1,2-dithioles (17), respectively. Upon treatment of thiazine perchlorates (3) with alkylhalides under basic conditions, acrylonitriles (18) are formed by the way 4 --> 5. Compounds (18) can be transformed to 1,2,4-triazoles (19).
• Kreutzberger; Kreutzberger, Arzneimittel-Forschung/Drug Research, 1980, vol. 30, # 2, p. 232 - 234
  作者：Kreutzberger、Kreutzberger

  DOI：——

  日期：——
• Regioselective hydrodehalogenation of 3,5-dihaloisothiazole-4-carbonitriles: synthesis of 3-haloisothiazole-4-carbonitriles
  作者：Heraklidia A. Ioannidou、Panayiotis A. Koutentis

  DOI：10.1016/j.tet.2011.03.065

  日期：2011.5

  3,5-Dibromoisothiazole-4-carbonitrile 1 treated with Zn or In dust (5 equiv) and HCO2H undergoes regioselective hydrodebromination to give 3-bromoisothiazole-4-carbonitrile 3 in 70-74% yield. Similarly, 5-bromo and iodo 3-chloroisothiazole-4-carbonitriles 8 and 9 give 3-chloroisothiazole-4-carbonitrile 4 in 77 and 85% yields, respectively. Also hydrodeamination of 5-amino-3-chloroisothiazole-4-carbonitrile 7 using isoamyl nitrite gives the latter in 95% yield. The dibromoisothiazole 1 reacts with Zn dust in either DCO2D or HCO2D to give 3-bromo-5-deuterioisothiazole-4-carbonitrile 10 in 71 and 58% yields, respectively. The 3-bromoisothiazole 3 reacts with cyclic dialkylamines to give the corresponding 2-(dialkylaminomethylene)-malononitriles and not the expected 3-dialkylaminoisothiazole-4-carbonitriles. Finally, the 3-bromoisothiazole 3 is readily converted into both 3-bromoisothiazole-4-carboxamide 19 and the carboxylic acid 20. All products are fully characterized. (C) 2011 Elsevier Ltd. All rights reserved.
• Hydrogenation of Imino‐bisnitriles—Synthesis of Novel Triamines
  作者：Raji Sundaramoorthi、Terence P. Keenan

  DOI：10.1080/00397910601038970

  日期：2007.2.1