5-氨基-2-甲基-2,3-二氢呋喃-4-甲腈 | 59790-76-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 中文名称: 5-氨基-2-甲基-2,3-二氢呋喃-4-甲腈
• 英文名称: 2-amino-5-methyl-4,5-dihydrofuran-3-carbonitrile
• 英文别名: 2-amino-4,5-dihydro-5-methyl-3-furancarbonitrile；5-amino-2-methyl-2,3-dihydrofuran-4-carbonitrile
• CAS: 59790-76-0
• 化学式: C₆H₈N₂O
• mdl: MFCD19203508
• 分子量: 124.142
• InChiKey: LQZMZAPEPTZBLO-UHFFFAOYSA-N

物化性质

• 熔点：
  106-108 °C
• 沸点：
  307.4±42.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-氨基-2-甲基-2,3-二氢呋喃-4-甲腈 在 吡啶 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.83h， 生成 N-(3-cyano-5-methylfuran-2-yl)-4-nitrobenzamide
  参考文献：
  名称：

  ROY Reclaims Its Crown: New Ways To Increase Polymorphic Diversity

  摘要：

  Chemical compounds that exist in multiple crystalline forms are said to exhibit polymorphism. Polymorphs have the same composition, but their structures and properties can vary markedly. In many fields, conditions for crystallizing compounds of interest are screened exhaustively to generate as many polymorphs as possible, from which the most advantageous form can be selected. We report new ways to search for polymorphs and increase polymorphic diversity, based on crystallization induced by suitably designed mixed-crystal seeds. The potential of the strategy has been demonstrated by using it to produce new polymorphs of the benchmark compound ROY as single crystals structurally characterized by X-ray diffraction. This allows ROY to reclaim its crown as the most polymorphic compound in the Cambridge Structural Database. More generally, the methods promise to become valuable tools for polymorphic screening in all fields where crystalline solids are used.

  DOI：

  10.1021/jacs.0c04434
• 作为产物：
  描述：

  2-cyano-4-oxopentanonitrile 在 sodium tetrahydroborate 作用下， 以 水 为溶剂， 以85%的产率得到5-氨基-2-甲基-2,3-二氢呋喃-4-甲腈
  参考文献：
  名称：

  Nasakin; Sheverdov; Moiseeva, Russian Journal of General Chemistry, 1999, vol. 69, # 2, p. 291 - 300

  摘要：

  DOI：

文献信息

• Synthesis of dihydrofuro[2,3-<i>b</i>]pyridines by the reaction of 2-amino-4,5-dihydro-3-furancarbonitriles with α,β-unsaturated carbonyl compounds
  作者：Hiroshi Maruoka、Motoyoshi Yamazaki、Yukihiko Tomioka

  DOI：10.1002/jhet.5570390420

  日期：2002.7

  The reactions of 2-amino-4,5-dihydro-3-furancarbonitriles 1a-d with α,β-unsaturated carbonyl compounds in the presence of sodium ethoxide (0.1 equivalent) gave the corresponding Michael adducts 2a-d, 3a-d and 4a-d. Compounds 2a-d and 3a-c reacted with sodium alkoxide (1 equivalent) to yield the corresponding 7a-alkoxyhexahydrofuro[2,3-b]pyridines 5a-d, 6a-d, 7a-c and 8a-c. Treatment of 5a-d, 6a-d,

  2-氨基-4,5-二氢-3-呋喃腈1a-d与α，β-不饱和羰基化合物在乙醇钠（0.1当量）存在下的反应得到相应的迈克尔加合物2a-d，3a-d和4a-d。化合物2a-d和3a-c与醇钠（1当量）反应，得到相应的7a-烷氧基六氢呋喃[2，3- b ]吡啶5a-d，6a-d，7a-c和8a-c。用叔丁醇钾处理5a-d，6a-d，7a-c和8a-c产生相应的二氢呋喃并[2,3- b ]吡啶图9a-d和10a-c。4a-c与乙醇钠（1当量）反应，得到相应的二氢呋喃[2，3- b ]吡啶11a-c。
• Testa, Maria G.; Perrini, Giancarlo; Chiacchio, Ugo, Journal of Chemical Research, Miniprint, 1993, # 8, p. 1921 - 1936
  作者：Testa, Maria G.、Perrini, Giancarlo、Chiacchio, Ugo、Corsaro, Antonio

  DOI：——

  日期：——
• Wamhoff, Heinrich; Thiemig, Heinz-Albrecht, Chemische Berichte, 1985, vol. 118, # 11, p. 4473 - 4485
  作者：Wamhoff, Heinrich、Thiemig, Heinz-Albrecht

  DOI：——

  日期：——
• Synthesis of 1,3-Oxazines and Furo[2,3-b]pyrans by reaction of 2-amino-4,5-dihydro-3-furancarbonitriles with dibenzoyldiazomethanes
  作者：Kenji Yamagata、Keiko Akizuki、Motoyoshi Yamazaki

  DOI：10.1002/prac.19983400108

  日期：——

  2-Amino-4,5-dihydro-3-furancarbonitriles (1) react with a slight excess of dibenzoyldiazomethane in the presence of rhodium(II) acetate to give 1,3-oxazin-4-ones (2). With three equivalents of dibenzoyldiazomethane compounds 1 react to afford furo[2,3-b]pyran-3a-carbonitriles (3). Compound 3a was also obtained by treatment of 2a with two equivalents of dibenzoyldiazomethane.
• Synthesis of 2-amino-3-cyano-4,5-dihydrofurans from ?,?-dicyanoketones
  作者：I. V. Moiseeva、P. M. Lukin、O. E. Nasakin、V. N. Romanov、V. A. Tafeenko、A. Kh. Bulai、P. A. Sharbatyan

  DOI：10.1007/bf00509720

  日期：1990.7