2-(Ethylamino)-6-methyl-4-oxochromene-3-carbaldehyde | 755009-17-7

• 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-(Ethylamino)-6-methyl-4-oxochromene-3-carbaldehyde
• CAS: 755009-17-7
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: XNDRIEIOYUBAHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(Ethylamino)-6-methyl-4-oxochromene-3-carbaldehyde 在 溶剂黄146 、 锌 作用下， 反应 4.0h， 以52%的产率得到3,6-二甲基-4-羟基香豆素
  参考文献：
  名称：

  Amine-Controlled Reduction of 2-Aminochromone-3-Carbaldehyde with Zn and Acetic Acid

  摘要：

  在乙酸中用锌加热 2-(N-芳基氨基)铬酮-3-羰基醛，可生成 2-(N-芳基氨基)-3-甲基香豆素，而 2-(N-烷基氨基)铬酮-3-羰基醛则可生成 4-羟基-3-甲基香豆素，产量适中。在非常温和的反应条件下，醛基还原成了甲基。

  DOI：

  10.3184/174751915x14477880702453
• 作为产物：
  描述：

  N-ethyl-1-(6-methyl-4-oxochromen-3-yl)methanimine oxide 以 乙醇 为溶剂， 反应 2.0h， 以98%的产率得到2-(Ethylamino)-6-methyl-4-oxochromene-3-carbaldehyde
  参考文献：
  名称：

  Rearrangements of N-alkyl-/aryl-nitrones derived from 4-oxo-4H-1-benzopyran-3-carboxaldehyde––a solvent-dependent process

  摘要：

  C-(4-Oxo-4H-1-benzopyran-3-yl)-N-alkyl-/aryl-nitrones derived from 4-oxo-4H-1-benzopyran-3-carboxaldehyde, rearrange to 2-alkyl-/aryl-amino-3-formylchromone and/or 3-(alkyl-/aryl-aminomethylene)chroman-2,4-dione depending upon the reaction medium. 3-(Alkylaminomethylene)chroman-2,4-dione has been utilized in the synthesis of 1-benzopyrano[3,4-d]isoxazole-4-one. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.06.033

文献信息

• Substituent-controlled domino-Knoevenagel-hetero Diels–Alder reaction—a one-pot synthesis of polycyclic heterocycles
  作者：Sourav Maiti、Suman Kalyan Panja、Chandrakanta Bandyopadhyay

  DOI：10.1016/j.tet.2010.07.028

  日期：2010.9

  The reaction of 2-(N-alkenyl-N-aryl)amino-4-oxo-4H-1-benzopyran-3-carbaldehyde with dimedone/Meldrum’s acid/4-hydroxycoumarin by heating in ethanol in the presence of pyridine produces polycyclic heterocycles bearing pyridine and pyran rings in a one-pot reaction. The effect of substituents on N-atom of the amino function controls the mode of reaction. Terminal alkenes prefer intramolecular Michael

  通过在吡啶存在下于乙醇中加热，使2-（N-烯基-N-芳基）氨基-4-氧代-4 H -1-苯并吡喃-3-甲醛与二甲酮/麦德鲁姆酸/ 4-羟基香豆素反应生成多环一锅反应中带有吡啶和吡喃环的杂环。取代基对氨基官能团的N-原子的影响控制了反应方式。末端烯烃偏爱分子内迈克尔型反应，但非末端烯烃偏爱Diels-Alder反应，而在类似条件下，2-（N-烷基-N-烯丙基）氨基-4-氧代-4 H -1-苯并吡喃-3 -甲醛经历多米诺-Knoevenagel-杂Diels-Alder反应。
• A one-pot synthesis of 3,3′-methylenebis(2-arylamino-4H-chromen-4-one) from C-(4-oxo-4H-1-benzopyran-3-yl)-N-arylnitrone
  作者：Sourav Maiti、Suman Kalyan Panja、Chandrakanta Bandyopadhyay

  DOI：10.1016/j.tetlet.2009.04.087

  日期：2009.7

  2-(Arylamino)-4-oxo-4H-chromene-3-carbaldehyde 3 (R2 = aryl) produces 12H-chromeno[2,3-b]quinolin-12-one 4 when treated with sarcosine, piperidine or diethylamine, but produces 3,3′-methylenebis(2-arylamino-4H-chromen-4-one) 8 when treated with the same amine in the presence of an excess of formaldehyde. Compound 3 (R2 = alkyl) was found to be less reactive than the N-aryl analogues towards the deformylative

  2-（芳基氨基）-4-氧代-4- ħ色烯-3-甲醛3（R 2  =芳基）产生12 ħ -chromeno [2,3- b ]喹啉-12-酮4当与肌氨酸，哌啶处理或二乙胺，但是当在过量甲醛存在下用相同的胺处理时，会生成3,3'-亚甲基双（2-芳基氨基-4 H-铬-4--4-酮）8。发现化合物3（R 2  ＝烷基）对N型芳基类似物的反应性低于N-芳基类似物。
• Bandyopadhyay, Chandrakanta; Sur, Kumar Ranabir; Patra, Ranjan, Journal of Chemical Research, Miniprint, 2003, # 8, p. 847 - 856
  作者：Bandyopadhyay, Chandrakanta、Sur, Kumar Ranabir、Patra, Ranjan、Banerjee, Subhabrata

  DOI：——

  日期：——
• Ghosh, Tarun; Patra, Ranjan; Bandyopadhyay, Chandrakanta, Journal of Chemical Research, 2004, # 1, p. 47 - 49
  作者：Ghosh, Tarun、Patra, Ranjan、Bandyopadhyay, Chandrakanta

  DOI：——

  日期：——
• An organocatalytic rearrangement of 2-(N-alkyl-/aryl-)amino-4-oxo-4H-1-benzopyran-3-carbaldehyde
  作者：Sourav Maiti、Suman Kalyan Panja、Chandrakanta Bandyopadhyay

  DOI：10.1016/j.tetlet.2011.02.053

  日期：2011.4

  2-(Arylamino)-4-oxo-4H-1-benzopyran-3-carbaldehyde rearranges to 4-oxo-4H-1-benzopyran-3-carbanilide when treated with glycine in the presence of formalin, but under similar conditions 2-(alkylamino)-4-oxo-4H-1-benzopyran-3-carbaldehyde rearranges to 3-alkylaminomethylenechroman-2,4-dione. (C) 2011 Elsevier Ltd. All rights reserved.