ethyl 2-amino-7,7-dimethyl-4-(3-nitrophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 2-amino-7,7-dimethyl-4-(3-nitrophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate
• 英文别名: ethyl-2-amino-4-(3-nitrophenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate；ethyl 2-amino-7,7-dimethyl-4-(3-nitrophenyl)-5-oxo-6,8-dihydro-4H-chromene-3-carboxylate
• 化学式: C₂₀H₂₂N₂O₆
• 分子量: 386.404
• InChiKey: CSKWEEXHBKWIOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  124
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 2-amino-7,7-dimethyl-4-(3-nitrophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate 在 六氯乙烷 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 10.5h， 生成 2-(4-chlorophenoxy)-3-(4-chlorophenyl)-8,8-dimethyl-5-(3-nitrophenyl)-8,9-dihydro-3H-chromeno[2,3-d]pyrimidine-4,6(5H,7H)-dione
  参考文献：
  名称：

  Synthesis of Novel 2-Aryloxy-3-(4-chlorophenyl)-8-substituted-5-aryl-8,9-dihydro-3H-chromeno[2,3-d]pyrimidine-4,6(5H,7H)-dione Derivatives

  摘要：

  Twenty‐one novel 2‐aryloxy‐3‐(4‐chlorophenyl)‐8‐substituted‐5‐aryl‐8,9‐dihydro‐3H‐chromeno[2,3‐d]pyrimidine‐4,6(5H,7H)‐diones 5a, 5b, 5c, 5d, 5e, 5f, 5g, 5h, 5i, 5j, 5k, 5l, 5m, 5n, 5o, 5p, 5q, 5r, 5s, 5t, 5u were designed and easily synthesized via a tandem aza‐Wittig reaction. Treatment of iminophosphorane 3 with 4‐chlorophenyl iso‐cyanate gave carbodiimide 4, which reacted with phenols to provide the title compounds in 50–73% isolated yields. All compounds 3 and 5 were confirmed by infrared, 1H‐NMR, mass spectra, and elemental analysis, and compound 5a was further analyzed by single‐crystal X‐ray diffraction, and the title compounds were synthesized with the purpose of bringing in some new chemical and biological interests.

  DOI：

  10.1002/jhet.2183
• 作为产物：
  描述：

  间硝基苯甲醛 在 potassium fluoride dihydrate 作用下， 以 乙二醇 为溶剂， 反应 6.0h， 生成 ethyl 2-amino-7,7-dimethyl-4-(3-nitrophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate
  参考文献：
  名称：

  Synthesis of Novel 2-Aryloxy-3-(4-chlorophenyl)-8-substituted-5-aryl-8,9-dihydro-3H-chromeno[2,3-d]pyrimidine-4,6(5H,7H)-dione Derivatives

  摘要：

  Twenty‐one novel 2‐aryloxy‐3‐(4‐chlorophenyl)‐8‐substituted‐5‐aryl‐8,9‐dihydro‐3H‐chromeno[2,3‐d]pyrimidine‐4,6(5H,7H)‐diones 5a, 5b, 5c, 5d, 5e, 5f, 5g, 5h, 5i, 5j, 5k, 5l, 5m, 5n, 5o, 5p, 5q, 5r, 5s, 5t, 5u were designed and easily synthesized via a tandem aza‐Wittig reaction. Treatment of iminophosphorane 3 with 4‐chlorophenyl iso‐cyanate gave carbodiimide 4, which reacted with phenols to provide the title compounds in 50–73% isolated yields. All compounds 3 and 5 were confirmed by infrared, 1H‐NMR, mass spectra, and elemental analysis, and compound 5a was further analyzed by single‐crystal X‐ray diffraction, and the title compounds were synthesized with the purpose of bringing in some new chemical and biological interests.

  DOI：

  10.1002/jhet.2183

文献信息

• Nanozeolite clinoptilolite as a highly efficient heterogeneous catalyst for the synthesis of various 2-amino-4H-chromene derivatives in aqueous media
  作者：Seyed Meysam Baghbanian、Niloufar Rezaei、Hamed Tashakkorian

  DOI：10.1039/c3gc41302k

  日期：——

  The preparation of pharmaceutically active 2-amino-4H-chromene derivatives has been achieved using a nano powder of natural clinoptilolite (CP) zeolite. A wide range of these worthy structures having diverse substituents on the 4H-chromene ring were efficiently synthesized via the reaction of an aromatic aldehyde and variety of enolizable C–H activated acidic compounds. Nano sized natural clinoptilolite

  使用天然斜发沸石（CP）沸石的纳米粉末已经实现了具有药物活性的2-氨基-4 H-色烯衍生物的制备。宽范围的具有4上的取代基不同的这些值得结构ħ色烯环被有效地合成通过芳香醛与各种可烯化的CH活化的酸性化合物的反应。通过行星球磨机械制备纳米级天然斜发沸石，并通过X射线衍射图谱（XRD），扫描电子显微镜图像（SEM）和透射电子显微镜（TEM）证实。在水性介质中评估了纳米CP的催化活性，结果表明其在有机合成中作为新型，绿色，可重复使用和有前景的催化剂的适用性。
• Improvement in nanocomposite host (nanocavity of dealuminated zeolite Y)-guest (12-molybdophosphoric acid) catalytic activity and its application to the one-pot three-component synthesis of tetrahydrobenzo[ b ]pyrans
  作者：Seyedeh Fatemeh Hojati、Maryam Moosavifar、Toktam Ghorbanipoor

  DOI：10.1016/j.crci.2016.11.005

  日期：2017.5

  efficient chemoselective synthesis of tetrahydrobenzo[b]pyran derivatives, and the corresponding products were obtained in good to excellent yields in very short reaction times. Furthermore, the catalytic activity of this new catalyst in the synthesis of tetrahydrobenzo[b]pyrans was compared with MPA encapsulated in zeolite Y dealuminated by the hydrothermal method. The catalyst (MPA–MDAZY) was recovered

  摘要 采用化学方法（乙二胺四乙酸）对沸石 Y 进行脱铝，以修饰沸石结构，以负载 12-磷酸钼酸 (MPA)。MPA 封装在改性脱铝沸石 Y (MDAZY) 的纳米腔中，并通过傅里叶变换红外、X 射线衍射和原子吸收光谱进行表征。新催化剂用于四氢苯并[b]吡喃衍生物的高效化学选择性合成，并在很短的反应时间内以良好至极好的收率获得了相应的产物。此外，将这种新催化剂在四氢苯并[b]吡喃合成中的催化活性与包封在通过水热法脱铝的沸石Y中的MPA进行了比较。
• Uncatalyzed Reactions in Aqueous Media: Three-Component, One-Pot, Clean Synthesis of Tetrahydrobenzo[b]pyran Derivatives
  作者：Sunita B. Bandgar、Babasaheb P. Bandgar、Balaji L. Korbad、Jalinder V. Totre、Sachin Patil

  DOI：10.1071/ch06461

  日期：——

  The synthesis of various tetrahydrobenzo[b]pyran derivatives has been carried out by means of an uncatalyzed, three-component, one-pot clean condensation of aromatic aldehydes, reactive methylene compounds, and dimidone in aqueous medium. Simple workup, and mild and neutral conditions that give quantitative yields of products in pure form, are the attractive features of this method.

  各种四氢苯并[b]吡喃衍生物的合成是通过芳香醛、反应性亚甲基化合物和二米酮在水介质中的非催化、三组分、一锅清洁缩合进行的。简单的后处理，温和和中性的条件，可以定量获得纯产品的产量，是这种方法的吸引人的特点。
• (<i>S</i>)-Proline as a Neutral and Efficient Catalyst for the One-Pot Synthesis of Tetrahydrobenzo[<i>b</i>]pyran Derivatives in Aqueous Media
  作者：Saeed Balalaie、Morteza Bararjanian、Ali Mohammad Amani、Barahman Movassagh

  DOI：10.1055/s-2006-926227

  日期：——

  (S)-Proline has been used as a mild, efficient and neutral catalyst for synthesis of various 4H-benzo[b]pyran derivatives via a one-pot three-component condensation of aromatic aldehydes, ­active methylene compounds, and dimedone in aqueous media. This method offers the advantages of proceeding and neutral and mild conditions, giving high to excellent yields of the products and simple workup.

  (S)-脯氨酸已被用作一种温和、高效且中性的催化剂，通过在水介质中一步三组分缩合反应，将芳香醛、活性甲基化合物和二甲基庚二酮合成各种4H-苯并[b]吡喃衍生物。该方法具有中性且温和的条件进行、产品收率高（从高到优秀）且后处理简单的优点。
• Catalyst Free One-pot Three-component Synthesis of 2-Amino-4Hchromene Derivatives in Aqueous Deep Eutectic Mixture at Room Temperature
  作者：Atul Chaskar

  DOI：10.2174/1570178611666140210213413

  日期：2014.4

  Multifunctional chromenes have been efficiently synthesized in aqueous medium at room temperature using deep eutectic mixture of choline chloride:urea. In this one-pot synthesis, the benzylidenemalononitrile firstly formed by Knoevenagel condensation of aldehyde and malononitrile eventually underwent Michael addition-cyclization with dimedone and offered the chromenes in good to excellent yield.

  在室温下的水相介质中，通过氯化胆碱与尿素的低共熔混合物，已高效合成了多功能色烯类化合物。在这一步法合成过程中，首先由醛与丙二腈的Knoevenagel缩合反应生成苄叉丙二腈，进而通过与二甲双酮的迈克尔加成-环化反应，以良好至优异的产率获得了色烯类化合物。