ethyl 2-amino-4-(2,4-dichlorophenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-benzo[b]pyrano-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-4-(2,4-dichlorophenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-benzo[b]pyrano-3-carboxylate
• 英文别名: 2-amino-3-ethoxycarbonyl-5,6,7,8-tetrahydro-7,7-dimethyl-5-oxo-4-(2',4'-dichlorophenyl)-4H-benzo[b]pyran；ethyl 2-amino-7,7-dimethyl-4-(2,4-dichlorophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate；ethyl-2-amino-4-(2,4-dichlorophenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate；ethyl 2-amino-4-(2,4-dichlorophenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate；ethyl 2-amino-4-(2,4-dichlorophenyl)-7,7-dimethyl-5-oxo-6,8-dihydro-4H-chromene-3-carboxylate
• 化学式: C₂₀H₂₁Cl₂NO₄
• 分子量: 410.297
• InChiKey: HJVJLIKZXOIBIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  27
• 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：
  78.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-amino-4-(2,4-dichlorophenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-benzo[b]pyrano-3-carboxylate 、 4-溴苯甲酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 乙腈 为溶剂， 以55.5%的产率得到ethyl 2-(4-bromobenzamido)-4-(2,4-dichlorophenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate
  参考文献：
  名称：

  Synthesis of 2-amide-3-carboxylate-4-aryl-4H-chromene derivatives

  摘要：

  在绿色介质-水中，四丁基溴化铵（TBAB）通过芳基醛、氰基乙酸酯和二甲基酮的三组分环缩合催化了4H-色烯的一锅合成。然后，4H-Chromene 与乙腈中的酰基氯在回流和 DMAP 催化下反应，以良好的收率生成了标题化合物。所有标题化合物的结构均通过 1H-核磁共振、质谱和元素分析得到证实。化合物 3n 的 X 射线晶体学显示其分子间存在很强的氢键。

  DOI：

  10.1007/s11164-012-0500-6
• 作为产物：
  描述：

  ethyl 2-cyano-3-(2,4-dichlorophenyl)acrylate 、 5,5-二甲基-1,3-环己二酮 在 苄基三乙基氯化铵 作用下， 反应 0.08h， 以97%的产率得到ethyl 2-amino-4-(2,4-dichlorophenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-benzo[b]pyrano-3-carboxylate
  参考文献：
  名称：

  Efficient Synthesis of Tetrahydrobenzo[b]pyrans under Solvent‐Free Conditions at Room Temperature

  摘要：

  A range of tetrahydrobenzo[b]pyrans have been synthesized in very good yields under solvent-free conditions by grinding alpha-cyanocinnamonitrils or beta-cyano-beta-carbethoxy styrene and 5,5-dimethyl-1,3-cyclohexanedione in the presence of TEBA as catalyst. The short reaction time, cleaner reaction, and easy workup make this protocol practical and economically attractive.

  DOI：

  10.1080/00397910600640230

文献信息

• 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。
• Synthesis of 2-amino-4-aryl-7,7-dimethyl-5-oxo-4<i>H</i>-5,6,7,8-tetrahydrobenzo[<i>b</i>]pyran derivatives in ionic liquid medium
  作者：Yuling Li、Baixiang Du、Xiangshan Wang、Daqing Shi、Shujiang Tu

  DOI：10.1002/jhet.5570430323

  日期：2006.5

  In this paper, preparation of 2-Amino-4-aryl-7,7-dimethyl-5-oxo-4H-5,6,7,8-tetrahydrobenzo[b]pyran derivatives from aromatic aldehyde, malononitrile or cyanoacetate and 5,5-dimethyl-1,3-cyclohexanedione in ionic liquid [bmim+][BF4−] was described. Compared with other methods, this new method has the advantages of easier work-up, milder reaction conditions, high yields and environmentally benign procedure

  本文从芳族醛，丙二腈或氰基乙酸酯和5制备2-氨基-4-芳基-7,7-二甲基-5-氧代-4 H -5,6,7,8-四氢苯并[ b ]吡喃衍生物，5-二甲基-1,3-环己二酮在离子液体[BMIM + ] [BF 4 - ]的说明。与其他方法相比，该新方法具有易于处理，反应条件温和，收率高和对环境有益的优点。
• 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。
• A new PEG-1000-based dicationic ionic liquid exhibiting temperature-dependent phase behavior with toluene and its application in one-pot synthesis of benzopyrans
  作者：Huizhen Zhi、Chunxu Lü、Qiang Zhang、Jun Luo

  DOI：10.1039/b822481a

  日期：——

  A new recyclable temperature-dependant phase-separation system comprised of PEG-1000-based dicationic acidic ionic liquid and toluene was developed and used in one-pot three-component condensation to prepare benzopyrans in excellent yields (up to 93%).

  开发了一种新的可回收温度依赖相分离系统，该系统由基于PEG-1000的二阳离子酸性离子液体和甲苯组成，并用于一锅法三组分缩合反应，制备了苯并众聚物，产率优异（高达93%）。