2-methyl-4-oxo-4H-<1>benzopyran-3-carbonitrile | 67140-88-9

• 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-methyl-4-oxo-4H-<1>benzopyran-3-carbonitrile
• 英文别名: 3-Cyano-2-methylchromone；2-methyl-4-oxochromene-3-carbonitrile
• CAS: 67140-88-9
• 化学式: C₁₁H₇NO₂
• 分子量: 185.182
• InChiKey: FBMGVJCYVULNFH-UHFFFAOYSA-N

物化性质

• 熔点：
  200-201 °C
• 沸点：
  287.4±40.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 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：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methyl-4-oxo-4H-<1>benzopyran-3-carbonitrile 生成 2-methylchromone-3-carboxylic acid
  参考文献：
  名称：

  Ghosh, Chandra Kanta; Pal, Chandana, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1985, vol. 24, p. 1288 - 1290

  摘要：

  DOI：
• 作为产物：
  描述：

  3-acetyl-4H-chromen-4-one 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以80%的产率得到2-methyl-4-oxo-4H-<1>benzopyran-3-carbonitrile
  参考文献：
  名称：

  Ghosh, Chandra Kanta; Pal, Chandana; Bhattacharyya, Atanu, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1985, vol. 24, p. 914 - 917

  摘要：

  DOI：

文献信息

• Iridium-catalyzed direct asymmetric vinylogous allylic alkylation
  作者：Chang-Yun Shi、Jun-Zhao Xiao、Liang Yin

  DOI：10.1039/c8cc07249c

  日期：——

  alkylation of α,β-unsaturated lactones (including coumarins) was achieved with excellent regio- and enantioselectivity. Transformations of the product were carried out by means of the versatile terminal olefin and lactone moieties. The synthetic application of the present methodology was showcased by the asymmetric synthesis of an advanced synthetic Merck intermediate toward a new drug candidate.

  α，β-不饱和内酯（包括香豆素）的催化不对称乙烯基烯丙基烷基化反应具有出色的区域和对映选择性。借助通用的末端烯烃和内酯部分进行产物的转化。通过先进的合成默克中间体向新药物候选者的不对称合成，展示了本方法学的合成应用。
• Facile syntheses of 2-substituted 3-cyanochromones
  作者：K.S. Levchenko、I.S. Semenova、V.N. Yarovenko、P.S. Shmelin、M.M. Krayushkin

  DOI：10.1016/j.tetlet.2012.05.031

  日期：2012.7

  A simple and general route to 3-cyanochromones containing various substituents on position 2 of the ring is developed. The method is based on condensation of 3-(2-hydroxyphenyl)-3-oxopropionitrile with acid chlorides or anhydrides in pyridine at room temperature.

  开发了一种简单且通用的方法来制备在环的2位上含有各种取代基的3-氰基色酮。该方法基于3-（2-羟基苯基）-3-氧代丙腈在室温下在吡啶中与酰氯或酸酐的缩合。
• Synthesis of unsymmetrical 4-oxo-2-vinyl-4H-chromene-3-carbonitrile dyes via Knoevenagel reaction
  作者：K.S. Levchenko、K.A. Chudov、E.V. Zinoviev、K.A. Lyssenko、D.U. Demin、N.O. Poroshin、P.S. Shmelin、E.P. Grebennikov

  DOI：10.1016/j.tetlet.2018.06.012

  日期：2018.7

  New 4-oxo-2-vinyl-4H-chromene-3-carbonitrile derivatives have been synthesized by the Knoevenagel reaction of 2-methyl-4-oxo-4H-chromene-3-carbonitrile with aromatic and heteroaromatic aldehydes. Spectral properties of the obtained compounds have been studied.

  通过2-甲基-4-氧代-4H-色烯-3-腈与芳香族和杂芳族醛的Knoevenagel反应合成了新的4-氧代-2-乙烯基-4H-色烯-3-腈。已经研究了所得化合物的光谱性质。
• Benzopyrans - XXXIII. [4+2]Cycloaddition of N,N-dimethylhydrazones and anils of 2-unsubstituted and 2-methyl-4-oxo-4H-1-benzopyran-3-carboxaldehyde with N-phenylmaleimide
  作者：Chandra Kanta Ghosh、Kaberi Bhattacharya、Chandreyi Ghosh

  DOI：10.1016/s0040-4020(01)85025-0

  日期：1994.4

  The chromone derivatives 1, 2, and 4 give with N-phenylmaleimide the cycloadducts 5, 12, and 13 which are converted by palladised charcoal into 2-azaxanthone 6, xanthones 14 and 15, respectively. Treatment of the azaxanthone 5 with acidic ethanol produces a mixture of salicyloylpyridines 7–9.

  的色酮衍生物1，2，和4给出具有Ñ苯基马来所述cycloadducts 5，12，和13其通过palladised炭转化成2-azaxanthone 6，呫14和15分别。用酸性乙醇处理氮杂蒽酮5会产生水杨基吡啶7–9的混合物。
• Domino reactions of 2-methyl chromones containing an electron withdrawing group with chromone-fused dienes
  作者：Jian Gong、Fuchun Xie、Wenming Ren、Hong Chen、Youhong Hu

  DOI：10.1039/c1ob06613g

  日期：——

  Domino reactions of 2-methyl substituted chromones containing an electron withdrawing group at the 3-position with chromone-fused dienes synthesized a diverse range of benzo[a]xanthones and complicated chromone derivatives. These multiple-step reactions result in either two or three new C–C bonds without a transition metal catalyst or an inert atmosphere.

  在3位上具有吸电子基团的2-甲基取代的色酮与色酮稠合的二烯的多米诺反应合成了多种苯并[ a ]氧杂蒽酮和复杂的色酮衍生物。这些多步反应可产生两个或三个新的C–C键，而无需过渡金属催化剂或惰性气氛。