3-(p-Tolyliminomethyl)-1-benzopyran-4(4H)-one | 138990-99-5

• 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: 3-(p-Tolyliminomethyl)-1-benzopyran-4(4H)-one
• 英文别名: 3-(p-Methylphenyliminomethyl)chromone；3-{[(4-methylphenyl)imino]methyl}-4H-chromen-4-one；3-(p-tolylimino-methyl)-chromen-4-one；3-[(4-Methylphenyl)iminomethyl]chromen-4-one
• CAS: 138990-99-5
• 化学式: C₁₇H₁₃NO₂
• 分子量: 263.296
• InChiKey: IECBBKCVQPHFMI-UHFFFAOYSA-N

物化性质

• 熔点：
  118 °C(Solv: ethanol (64-17-5))
• 沸点：
  410.3±45.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(p-Tolyliminomethyl)-1-benzopyran-4(4H)-one 、 苯乙酰氯 生成 2-Methylphenyl-10H-<1>benzopyrano<3,2-c>pyridine-3,10(2H)-dione
  参考文献：
  名称：

  Fitton,A.O. et al., Journal of the Chemical Society. Perkin transactions I, 1977, p. 1450 - 1452

  摘要：

  DOI：
• 作为产物：
  描述：

  乙烷,三氯氟- 、 色酮-3-甲醛 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 以70%的产率得到3-(p-Tolyliminomethyl)-1-benzopyran-4(4H)-one
  参考文献：
  名称：

  Indium triflate: a new catalyst for (4 + 2)-cycloaddition of chromone Schiff ’s bases

  摘要：

  在三氟甲磺酸铟和钪的存在下，在环境温度和压力下，3,4-二氢-2H-吡喃与各种色酮席夫碱 3 反应，以高产率区域特异性地生成内环加合物 4。

  DOI：

  10.1039/b000923g

文献信息

• <i>N</i>-[[(Chlorosulfinyl)oxy]methylene]-<i>N</i>-methylmethanaminium Chloride as A Dehydrating Agent. A Direct and Efficient One-Pot Synthesis of Various Pyrimidinones, Azetidinones and Pyridones via Cycloaddition Reactions
  作者：Satyendra P. Singh、Asha R. Mahajan、Dipak Prajapati、Jagir S. Sandhu

  DOI：10.1055/s-1991-26639

  日期：——

  N-[[(Chlorosulfinyl)oxy]methylene]-N-methylmethanaminium chloride (1) is found to be an efficient and mild dehydrating agent for the in situ generation of monophenyl- (4a) diphenyl- (4b) and monochloroketenes (4c) directly from the corresponding carboxylic acids 2. These ketenes undergo cycloaddition reactions with 1,3-diaza-1, 3-butadienes 5 to afford 4(3H)-pyrimidinones 6 and azetidones 7, and with 3-(aryliminomethyl)chromones 8 to give [1]benzopyrano[3,2-c]pyridine-3,10[2H]diones 9.

  N-[(氯磺酰氧基)亚甲基]-N-甲基甲铵氯（1）被发现是一种高效且温和的脱水剂，可直接从相应的羧酸2原位生成单苯基（4a）、二苯基（4b）和单氯代烯酮（4c）。这些烯酮与1,3-二氮-1,3-丁二烯5发生环加成反应，生成4(3H)-嘧啶酮6和氮杂环丁烷酮7，并与3-(芳亚甲基)色酮8反应，得到[1]苯并吡喃[3,2-c]吡啶-3,10[2H]二酮9。
• Indium triflate: a new catalyst for (4 + 2)-cycloaddition of chromone Schiff ’s bases
  作者：Sunil Gadhwal、Jagir S. Sandhu

  DOI：10.1039/b000923g

  日期：——

  3,4-Dihydro-2H-pyran reacts with a variety of chromone Schiff’s bases 3 in the presence of indium and scandium triflates at ambient temperature and pressure to give the endo cycloadducts 4 regiospecifically in high yields.

  在三氟甲磺酸铟和钪的存在下，在环境温度和压力下，3,4-二氢-2H-吡喃与各种色酮席夫碱 3 反应，以高产率区域特异性地生成内环加合物 4。
• Schiff bases of 3-formylchromone as thymidine phosphorylase inhibitors
  作者：Khalid Mohammed Khan、Nida Ambreen、Sajjad Hussain、Shahnaz Perveen、M. Iqbal Choudhary

  DOI：10.1016/j.bmc.2009.03.020

  日期：2009.4

  3-Formylchromone (1), 3-methyl-7-hydroxychromone (2) and Schiff bases of 3-formylchromone 3-19 have been synthesized and their anti-thymidine phosphorylase inhibitory activity was evaluated. Compounds 1-19 showed a varying degree of thymidine phosphorylase inhibition with IC50 values 19.77 +/- 3.25 to 480.21 +/- 2.34 mu M. Their activity was compared with the standard 7-deazaxanthine (IC50 = 39.28 +/- 0.76 mu M). Compound 12 showed an excellent thymidine phosphorylase inhibitory activity with an IC50 value of 19.77 +/- 3.25 mu M, better than the standard. Compound 4 also showed an excellent inhibitory activity (IC50 = 40.29 +/- 4.56 mu M). The parent 3-formylchromone (1) and 3-methyl-7-hydroxychromone (2) were found to be inactive. The structures of the compounds were elucidated by using spectroscopic techniques, including H-1 NMR, EI MS, IR, UV and elemental analysis. (C) 2009 Elsevier Ltd. All rights reserved.
• Prajapati, Dipak; Mahajan, Asha R.; Sandhu, Jagir S., Journal of the Chemical Society. Perkin transactions I, 1992, # 14, p. 1821 - 1824
  作者：Prajapati, Dipak、Mahajan, Asha R.、Sandhu, Jagir S.

  DOI：——

  日期：——
• Synthesis of 3-aminomethylidenechroman-2-carboxamides by a Sequential One-pot Three Component Reaction and by Post-Passerini Condensation Modification
  作者：Jaydip Ghosh、Suman Kalyan Panja、Sourav Maiti、Pritam Biswas、Tapas Sarkar、Chandrakanta Bandyopadhyay

  DOI：10.1002/jhet.1929

  日期：2016.3

  has been synthesized by a one‐pot three component reaction among 3‐formylchromone, aromatic amine, and cyclohexyl isocyanide. 3‐(N‐alkylsubstitued/unsubstituted)aminomethylidenechroman‐2‐carboxamides were synthesized by heating Passerini products derived from chromone‐3‐carbaldehyde with different aliphatic primary amines. The products obtained from the reactions of aliphatic primary amines readily

  3-芳基氨基亚甲基苯并二氢呋喃-2-羧酰胺是通过3-甲酰基色酮，芳族胺和环己基异氰化物之间的一锅三组分反应合成的。3-（N-烷基取代/未取代）氨基亚甲基苯并二氢呋喃-2-羧酰胺是通过将衍生自苯并三苯甲醛的帕塞里尼产品与不同的脂肪族伯胺加热合成的。脂肪族伯胺反应制得的产物在乙酸中加热时很容易形成苯并[2,3-c]吡咯。还使用该方法合成了双色酮。