ethyl 2-amino-4-phenyl-7,7-dimethyl-5-oxo-4H-5,6,7,8-tetrahydrobenzo[b]pyran-3-carboxylate | 107752-93-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-amino-4-phenyl-7,7-dimethyl-5-oxo-4H-5,6,7,8-tetrahydrobenzo[b]pyran-3-carboxylate
• 英文别名: 2-amino-5,6,7,8-tetrahydro-5-oxo-4-phenyl-7,7-dimethyl-4H-benzo--pyran-3-ethylcarboxylate；2-amino-3-ethoxycarbonyl-5,6,7,8-tetrahydro-7,7-dimethyl-5-oxo-4-phenyl-4H-benzo[b]pyran；2-amino-7,7-dimethyl-3-ethoxycarbonyl-5-oxo-4-phenyl-5,6,7,8-tetrahydro-4H-benzo[b]pyran；2-amino-3-ethylacetato-4-(phenyl)-7,7-dimethyl-5-oxo-4H-5,6,7,8-tetrahydrobenzo[b]pyran；ethyl 2-amino-7,7-dimethyl-5-oxo-4-phenyl-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate；ethyl 2-amino-7,7-dimethyl-5-oxo-4-phenyl-6,8-dihydro-4H-chromene-3-carboxylate
• CAS: 107752-93-2
• 化学式: C₂₀H₂₃NO₄
• 分子量: 341.407
• InChiKey: LRNXUFGJTBOSHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 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-phenyl-7,7-dimethyl-5-oxo-4H-5,6,7,8-tetrahydrobenzo[b]pyran-3-carboxylate 在 ammonium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 6.0h， 以65%的产率得到7,7-dimethyl-2,5-dioxo-4-phenyl-1,2,3,4-tetrahydrocyclohexanopyridin-3-carboxamide
  参考文献：
  名称：

  Elnagdi, Mohamed Hilmy; Aal, Fatma Abdel Maksoud Abdel; Yassin, Youssef Mahfouz, Journal fur praktische Chemie (Leipzig 1954), 1989, vol. 331, # 6, p. 971 - 976

  摘要：

  DOI：
• 作为产物：
  描述：

  氰乙酸乙酯 在 potassium fluoride dihydrate 作用下， 以 乙二醇 为溶剂， 反应 6.0h， 生成 ethyl 2-amino-4-phenyl-7,7-dimethyl-5-oxo-4H-5,6,7,8-tetrahydrobenzo[b]pyran-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

• Potassium-Exchanged Zirconium Hydrogen Phosphate [α-Zr(KPO4)2]-Catalyzed Synthesis of 2-Amino-4H-pyran Derivatives under Solvent-Free Conditions
  作者：Ornelio Rosati、Azzurra Pelosi、Andrea Temperini、Vittorio Pace、Massimo Curini

  DOI：10.1055/s-0035-1560411

  日期：——

  conditions. A high-yielding, one-pot, three-component synthesis of functionalized 2-amino-4H-pyrans from β-dicarbonyl compounds, activated cyanomethylene compounds, and aldehydes, mediated by potassium-exchanged zirconium hydrogen phosphate [α-Zr(KPO4)2], is reported. The protocol shows excellent versatility, as it can be applied to aromatic, aliphatic, or α,β-unsaturated aldehydes under solvent-free conditions

  摘要 由钾交换磷酸氢锆[α-Zr（KPO）介导的由β-二羰基化合物，活化的氰基亚甲基化合物和醛类合成的高产一锅三组分功能化2-氨基-4 H-吡喃4）2 ]，被报告。该协议具有出色的通用性，因为它可以在无溶剂条件下应用于芳族，脂族或α，β-不饱和醛。 由钾交换磷酸氢锆[α-Zr（KPO）介导的由β-二羰基化合物，活化的氰基亚甲基化合物和醛类合成的高产一锅三组分功能化2-氨基-4 H-吡喃4）2 ]，被报告。该协议具有出色的通用性，因为它可以在无溶剂条件下应用于芳族，脂族或α，β-不饱和醛。
• Nano α-Al₂O₃supported ammonium dihydrogen phosphate (NH₄H₂PO₄/Al₂O₃): preparation, characterization and its application as a novel and heterogeneous catalyst for the one-pot synthesis of tetrahydrobenzo[b]pyran and pyrano[2,3-c]pyrazole derivatives
  作者：Behrooz Maleki、Samaneh Sedigh Ashrafi

  DOI：10.1039/c4ra07813f

  日期：——

  8-tetrahydrobenzo[b]pyrans and 6-amino-5-cyano-4-aryl-1,4-dihydropyrano[2,3-c]pyrazoles from the condensation of various aldehydes, malononitrile, and 1,3-dicarbonyl compounds (1,3-cyclohexanedione or 5,5-dimethyl-1,3-cyclohexanedione) or 3-methyl-1-phenyl-2-pyrazoline-5-one, using NH4H2PO4/Al2O3 with good yields. The use of easily available catalyst, shorter reaction times, better yields, the simplicity of the reaction

  为制备2-氨基-3-氰基-4-芳基-7,7-二甲基-5,6,7,8-四氢苯并[ b ]吡喃和6-氨基的简单，有效和环境友好的方法被开发出来。来自各种醛，丙二腈和1,3-二羰基化合物（1,3-环己二酮或5,5-二甲基）缩合的-5-氰基-4-芳基-1,4-二氢吡喃并[2,3- c ]吡唑-1,3-环己二酮）或3-甲基-1-苯基-2-吡唑啉-5-酮，使用NH 4 H 2 PO 4 / Al 2 O 3产量高。使用容易获得的催化剂，更短的反应时间，更好的产率，反应的简单性，非均相系统和容易的后处理是本方法的优点。催化剂的表征是通过FT-IR光谱，X射线衍射（XRD）技术，热分析（TG / DTG）和透射电子显微镜（TEM）进行的。
• 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。
• Silica-coated magnetic NiFe2O4 nanoparticles-supported H3PW12O40; synthesis, preparation, and application as an efficient, magnetic, green catalyst for one-pot synthesis of tetrahydrobenzo[b]pyran and pyrano[2,3-c]pyrazole derivatives
  作者：Behrooz Maleki、Hossein Eshghi、Mohammad Barghamadi、Negar Nasiri、Amir Khojastehnezhad、Samaneh Sedigh Ashrafi、Omid Pourshiani

  DOI：10.1007/s11164-015-2198-8

  日期：2016.4

  characterization, its catalytic activity was investigated in the synthesis of tetrahydrobenzo[ b ]pyran and pyrano[2,3- c ]pyrazole derivatives. Graphical Abstract (1) Novel silica-coated magnetic NiFe2O4 nanoparticles-supported H3PW12O40 was fabricated and characterized. (2) Recyclability of the catalyst. (3) Avoiding use of corrosive acid catalysts. (4) Green chemistry.

  摘要通过将Keggin（H 3 PW 12 O 40）杂多酸（HPA）化学 负载在二氧化硅包覆的NiFe上，制备了一种功能强大的磁性负载型酸催化剂NiFe 2 O 4 @SiO 2 -H 3 PW 12 O 40。2 O 4磁性纳米粒子。XRD，TEM，SEM，VSM和FTIR证实，Keggin HPA分散在二氧化硅包覆的NiFe 2 O 4表面上磁性纳米粒子。磁性可回收的催化剂可以容易地循环至少六次而不会显着降低催化活性。充分表征后，在四氢苯并[ b ]吡喃和吡喃并[2,3- c ]吡唑衍生物的合成中研究了其催化活性 。 图形摘要 （1）制备并表征了新型的二氧化硅包覆的磁性NiFe 2 O 4纳米粒子负载的H 3 PW 12 O 40。（2）催化剂的可回收性。（3）避免使用腐蚀性酸催化剂。（4）绿色化学。