ethyl‐2‐amino‐7,7‐ dimethyl‐5‐oxo‐4‐(p‐tolyl)‐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‐5‐oxo‐4‐(p‐tolyl)‐5,6,7,8‐tetrahydro‐4H‐chromene‐3‐carboxylate
• 英文别名: 2-amino-7,7-dimethyl-5-oxo-4-(4-methylphenyl)-5,6,7,8-tetrahydro-4H-chromene-3-carboxylic acid ethyl ester；ethyl 2-amino-7,7-dimethyl-5-oxo-4-(4-methylphenyl)-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate；ethyl-2-amino-7,7-dimethyl-5-oxo-4-(p-tolyl)-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate；ethyl 2-amino-7,7-dimethyl-4-(4-methylphenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate；ethyl 2-amino-7,7-dimethyl-4-(4-methylphenyl)-5-oxo-6,8-dihydro-4H-chromene-3-carboxylate
• 化学式: C₂₁H₂₅NO₄
• 分子量: 355.434
• InChiKey: VMTJJPYJWCLDPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  78.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  氰乙酸乙酯 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 生成 ethyl‐2‐amino‐7,7‐ dimethyl‐5‐oxo‐4‐(p‐tolyl)‐5,6,7,8‐tetrahydro‐4H‐chromene‐3‐carboxylate
  参考文献：
  名称：

  Synthesis of Substituted Tetrahydrochromenes by the Reactions of α,β-Unsaturated Cyanoesters with Dimedone/1,3-Cyclohexanedione

  摘要：

  Ethyl esters of 2-cyano-3-arylacrylic acid 1a-d (a=4-CH3-C6H4-, b=4-N(CH3)(2)-C6H4-, c=2-CH3O-C6H4-, d=2-Cl-C6H4-) reacted with 5,5-dimethyl-1,3-cyclohexanedione (2p, Y=CH3), and 1e-g (e=4-CH3-C6H4-, f=2-CH3O-C6H4-, g=2-Cl-C6H4-) reacted with 1,3-cyclohexanedione (2q, Y=H) in the presence of alcoholic sodium ethoxide to give the corresponding ethyl esters of 2-amino-7,7-dimethyl-5-oxo-4-aryl-5,6,7,8-tetrahydro-4H-chromene-3-carboxylic acid 4a-d and 2-amino-5-oxo-4-aryl-5,6,7,8-tetrahydro-4H-chromene-3-carboxylic acid 4e-g. The structures of the compounds 4a-g were confirmed by their ultraviolet, infrared, H-1 NMR, C-13 NMR, and mass spectral data and elemental analyses.

  DOI：

  10.1080/00397911.2010.515346

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。
• 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 nano-organo catalyzed route towards the efficient synthesis of benzo[b]pyran derivatives under ultrasonic irradiation
  作者：Ridaphun Nongrum、Geetmani Singh Nongthombam、Mattilang Kharkongor、Jims World Star Rani、Noimur Rahman、Chingrishon Kathing、Bekington Myrboh、Rishanlang Nongkhlaw

  DOI：10.1039/c6ra24108e

  日期：——

  reaction time and use of green solvents. Ultrasound energy has been meticulously exploited for the synthesis of a nano-organocatalyst as well as for the preparation of several benzo[b]pyran derivatives. The biological activity of the synthesized benzo[b]pyrans were investigated and one of the derivatives was found to demonstrate profound activity in suppressing the side-effects of chlorpyrifos, an insecticide

  本文报道了在超声条件下由维生素B 1官能化的Fe 2 O 3 @SiO 2 NPs催化的高效一锅合成苯并[ b ]吡喃。纳米有机催化剂的合成和表征通过FT-IR，TEM，EDS，粉末X射线衍射，等等若干苯并[ b以令人满意的产率制备了]吡喃衍生物，并且磁性回收和再循环了纳米催化剂。该方案的显着特征包括方便的后处理程序，温和的反应条件，容易的催化剂回收，较短的反应时间和绿色溶剂的使用。超声波能量已经被精心开发用于合成纳米有机催化剂以及制备几种苯并[ b ]吡喃衍生物。合成的苯并[生物活性b ]吡喃进行了调查和衍生物中的一种被发现表现出在抑制毒死蜱的副作用，对的外部鳃的形态杀虫剂深刻活性黑眶蟾蜍蝌蚪。
• 1,4-Diazabicyclo[2.2.2]octane as an Efficient Catalyst for a Clean, One-Pot Synthesis of Tetrahydrobenzo[b]pyran Derivatives via Multicomponent Reaction in Aqueous Media
  作者：Daryoush Tahmassebi、Jessica A. Bryson、Sophia I. Binz

  DOI：10.1080/00397911.2010.515345

  日期：2011.9.15

  mild and efficient catalyst for the synthesis of various tetrahydrobenzo[b]pyran derivatives via a one-pot, three component condensation of aromatic aldehydes, dimedone, and active methylene compounds. This method provides several advantages: a simple workup procedure, environmental friendliness, neutral conditions, and good yields. In addition, water or 50% aqueous ethanol was chosen as a green solvent

  摘要 1,4-二氮杂双环[2.2.2]辛烷 (DABCO) 已被用作一种温和高效的催化剂，通过芳香醛、二甲酮、和活性亚甲基化合物。这种方法提供了几个优点：简单的后处理程序、环境友好、中性条件和良好的收率。此外，选择水或 50% 乙醇水溶液作为绿色溶剂。