2-Imino-3-methyl-2H-1-benzopyran-3-carbonitrile | 41078-17-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-Imino-3-methyl-2H-1-benzopyran-3-carbonitrile
• 英文别名: 2-Imino-4-methyl-2H-1-benzopyran-3-carbonitrile；3-cyano-4-methyl-benzopyran-2-imine；4-Methyl-3-cyanocoumarinimide；3-Cyan-4-methyl-iminocumarin；2-imino-4-methyl-2H-chromene-3-carbonitrile；2-imino-4-methylchromene-3-carbonitrile
• CAS: 41078-17-5
• 化学式: C₁₁H₈N₂O
• 分子量: 184.197
• InChiKey: IFYWXSYHMKSWQH-UHFFFAOYSA-N

物化性质

• 熔点：
  147 °C
• 沸点：
  285.0±50.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  56.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Imino-3-methyl-2H-1-benzopyran-3-carbonitrile 在 哌啶 、 盐酸 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 0.5h， 生成 4-[(E)-2-[4-(dimethylamino)phenyl]ethenyl]-2-oxochromene-3-carbonitrile
  参考文献：
  名称：

  On the condensation of 2,2-difluoro-4-methyl-benzo[d]-1,3,2-dioxaborines with cyano acetic acid derivatives. Formation and transformation of 3-cyano-4-methyl-benzo[b]pyran-2-ones and their 2-imine precursors

  摘要：

  By condensation of 2,2-difluoro-4-methyl-benzo[d]-1,3,2-2H-dioxaborines (12) with cyano acetic acid derivatives in presence of weak bases, 3-cyano-4-methyl-benzo[b]pyran-2-ones (13) or their 3-cyano-4-methyl-benzo[b]pyran-2-imine precursors (14) are available in satisfactory yields.

  DOI：

  10.1007/bf00807640
• 作为产物：
  描述：

  2'-羟基苯乙酮 在 哌啶 作用下， 以 甲苯 、 苯 为溶剂， 反应 0.58h， 生成 2-Imino-3-methyl-2H-1-benzopyran-3-carbonitrile
  参考文献：
  名称：

  Manrao, M. R.; Kohli, Sunita; Kalsi, P. S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1984, vol. 23, # 11, p. 1130 - 1132

  摘要：

  DOI：

文献信息

• Formation of polyheterocyclic systems by reaction of 2-imino-4-methyl-2H-1-benzopyran-3-carbonitrile with active methylene compounds
  作者：Conor N. O'Callaghan、T. Brain H. McMurry、John E. O'Brien、Sylvia M. Draper、Deborah J. Wilcock

  DOI：10.1039/p19960001067

  日期：——

  2-Imino-4-methyl-2H-1-benzopyran-3-carbonitrile undergoes [1,5] tautomerism in solution to 2-amino-4-methylidene-4H-1-benzopyran-3-carbonitrile. Reaction with one equivalent of compounds containing a reactive methylene group affords simple 4-methylbenzopyran derivatives, and a methylidene derivative (of [1]benzopyrano[2,3-b][1,8]naphthyridine). Reaction with two and three equivalents of malononitrile affords derivatives of [1]benzopyrano[2,3,4-de]quinoline and [1]benzopyrano[2,3,4-de][1,6]-naphthyridine, which had previously been formulated as bicyclic benzopyran derivatives. The X-ray crystal structure of ethyl 3-amino-2-cyano-3-(2-imino-4-methyl-2H-1-benzopyran-3-yl)prop-2-enoate has been determined, showing the presence of two molecules in the asymmetric unit.

  2-亚氨基-4-甲基-2H-1-苯并吡喃-3-甲腈在溶液中发生[1,5]互变异构，生成2-氨基-4-亚甲基-4H-1-苯并吡喃-3-甲腈。与一当量含有活性亚甲基的化合物反应，得到简单的4-甲基苯并吡喃衍生物和亚甲基衍生物（[1]苯并吡喃并[2,3-b][1,8]萘啶）。与两当量和三当量的丙二腈反应，得到[1]苯并吡喃并[2,3,4-去]喹啉和[1]苯并吡喃并[2,3,4-去][1,6]-萘啶的衍生物，其先前已被配制为双环苯并吡喃衍生物。 3-氨基-2-氰基-3-(2-亚氨基-4-甲基-2H-1-苯并吡喃-3-基)丙-2-烯酸乙酯的X射线晶体结构已确定，表明存在不对称单元中的两个分子。
• Synthesis, characterization, antimicrobial activities and electrochemical behavior of new phenolic azo dyes from two thienocoumarin amines
  作者：Kamal S. D. Djeukoua、Emmanuel S. Fondjo、Jean-de-Dieu Tamokou、Joseph Tsemeugne、Peter F. W. Simon、Appolinaire Tsopmo、Francis M. M. Tchieno、Steve E. Ekom、Chancellin N. Pecheu、Ignas K. Tonle、Jules-Roger Kuiateb

  DOI：10.24820/ark.5550190.p010.994

  日期：——

  The coupling reactions of diazotized thienocoumarin derivatives with p-acetaminophen, salicylic acid and acetylsalicylic acid gave four products in which the benzene ring of the phenolic reagents were primarily substituted by two 3-diazenyl-4H-thieno[3,4-c]chromen-4-one or 3-diazenyl-4-imino-4H-thieno[3,4-c]chromene moieties. The newly prepared azo dyes were fully characterized based on their analytical and spectroscopic data. The electrochemical analysis of the novel azo dyes carried out on a glassy carbon electrode unequivocally further confirmed the assigned structures. The synthesized compounds tested for their antimicrobial activity using broth microdilution method, showed good activities.[GRAPHICS].
• Lithium bromide as a new catalyst for carbon–carbon bond formation in the solid state
  作者：Dipak Prajapati、Kushal C. Lekhok、Jagir S. Sandhu、Anil C. Ghosh

  DOI：10.1039/p19960000959

  日期：——

  Lithium bromide catalyses the condensation of carbonyl compounds with active methylene compounds in the absence of solvent, to afford olefinic products in high yields.
• Seema; Kumar, Surender; Makrandi, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005, vol. 44, # 6, p. 1307 - 1308
  作者：Seema、Kumar, Surender、Makrandi

  DOI：——

  日期：——
• MANRAO, M. R.;KOHLI, SUNITA;KALSI, P. S.;SHARMA, R. C.;JHOOTY, J. S., INDIAN J. CHEM., 1984, 23, N 11, 1130-1132
  作者：MANRAO, M. R.、KOHLI, SUNITA、KALSI, P. S.、SHARMA, R. C.、JHOOTY, J. S.

  DOI：——

  日期：——