ethyl 2-amino-4-(4-chlorophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate | 107752-88-5

• 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-(4-chlorophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate
• 英文别名: ethyl 2-amino-4-(4-chlorophenyl)-5-oxo-4,6,7,8-tetrahydrochromene-3-carboxylate
• CAS: 107752-88-5
• 化学式: C₁₈H₁₈ClNO₄
• 分子量: 347.798
• InChiKey: NAOZUHXAJDKWOV-UHFFFAOYSA-N

物化性质

• 熔点：
  183-184 °C(Solv: ethanol (64-17-5))
• 沸点：
  540.8±50.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 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-(4-chlorophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate 在 六氯乙烷 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 6.0h， 生成
  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：

  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-(4-chlorophenyl)-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

• Silica-bonded 5-n-propyl-octahydro-pyrimido[1,2-a]azepinium chloride (SB-DBU)Cl as a highly efficient, heterogeneous and recyclable silica-supported ionic liquid catalyst for the synthesis of benzo[b]pyran, bis(benzo[b]pyran) and spiro-pyran derivatives
  作者：Alireza Hasaninejad、Nooshin Golzar、Maryam Beyrati、Abdolkarim Zare、Mohammad Mahdi Doroodmand

  DOI：10.1016/j.molcata.2013.02.022

  日期：2013.6

  The reaction of 3-chloropropyl silica (SilprCl) with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in dry acetone affords silica-bonded 5-n-propyl-octahydro-pyrimido[1,2-a]azepinium chloride (SB-DBU)Cl as a new silica-supported ionic liquid catalyst. Afterward, (SB-DBU)Cl is used for the efficient synthesis of 4H-benzo[b]pyran derivatives via the one-pot, three-component reaction of carbonyl compounds (cyclohexane-1

  3-氯丙基二氧化硅（SilprCl）与1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU）在干燥的丙酮中的反应得到二氧化硅键合的5-正丙基-八氢-嘧啶基[1,2- a]氯化ze嗪（SB-DBU）Cl作为新型的二氧化硅负载型离子液体催化剂。之后，（SB-DBU）Cl通过羰基化合物（环己烷-1,3-二酮，5,5-一锅法）的三锅法有效合成4 H-苯并[ b ]吡喃衍生物。（1，3-二甲基环己烷-1，3-二酮或3-甲基-1-苯基-2-吡唑啉-5-酮）与芳族醛和烷基丙二酸酯。此外，一些新颖的双（苯并[ b使用（SB-DBU）Cl合成[] pyran] s和在结构上含有羟吲哚和/或喹喔啉部分的多种结构多样的螺-吡喃。将催化剂循环使用十五次，收率不变。
• Silica bonded n-propyl-4-aza-1-azoniabicyclo[2.2.2]octane chloride (SB-DABCO): A highly efficient, reusable and new heterogeneous catalyst for the synthesis of 4H-benzo[b]pyran derivatives
  作者：Alireza Hasaninejad、Mohsen Shekouhy、Nooshin Golzar、Abdolkarim Zare、Mohammad Mahdi Doroodmand

  DOI：10.1016/j.apcata.2011.04.012

  日期：2011.7

  3-chloropropyl silica with diazabicyclo[2.2.2]octane in dry acetone affords silica bonded n-propyl-4-aza-1-azoniabicyclo[2.2.2]octane chloride (SB-DABCO) as a new basic catalyst. The catalyst is used for the efficient synthesis of 4H-benzo[b]pyran derivatives via one-pot three-component reaction of cyclic ketones/1,3-diketones with aromatic aldehydes and alkylmalonates.

  3-氯丙基二氧化硅与二氮杂双环[2.2.2]辛烷在干燥丙酮中的反应提供了与二氧化硅键合的正丙基-4-氮杂-1-氮杂双环[2.2.2]辛烷氯化物（SB-DABCO），作为一种新的碱性催化剂。通过环酮/ 1,3-二酮与芳族醛和丙二酸烷基酯的一锅三组分反应，该催化剂可用于高效合成4 H-苯并[ b ]吡喃衍生物。
• Efficient tandem synthesis of a variety of pyran-annulated heterocycles, 3,4-disubstituted isoxazol-5(4H)-ones, and α,β-unsaturated nitriles catalyzed by potassium hydrogen phthalate in water
  作者：Hamzeh Kiyani、Fatemeh Ghorbani

  DOI：10.1007/s11164-014-1863-7

  日期：2015.10

  A variety of 4H-chromenes, benzochromenes, 4,5-dihydropyrano[3,2-c]chromenes, 4H-pyran-3-carboxylates, and 3,4-disubstituted isoxazol-5(4H)-ones have been synthesized in high yields by using potassium hydrogen phthalate (KHP) as an inexpensive, commercially available catalyst. It was found that the three-component tandem reaction enabled synthesis of pyran-annulated heterocycles in water at 50 °C. 3,4-Disubstituted isoxazol-5(4H)-ones were synthesized by use of 10 mol% KHP in water at room temperature. Also, treatment of methylene-containing compounds (malononitrile or ethyl cyanoacetate) with aromatic aldehydes in the presence of 5 mol% KHP resulted in α,β-unsaturated nitriles. The procedure is an easily performed, straightforward method for synthesis of a variety of pyran-annulated compounds, isoxazol-5(4H)-one-containing heterocycles, and Knoevenagel adducts. The reaction is safe, uses mild conditions, and is environmentally benign. Other notable advantages are reuse of the catalyst, no use of hazardous organic solvents, and ease of work-up.

  合成了一系列4H-克罗梅、苯并克罗梅、4,5-二氢吡喃[3,2-c]克罗梅、4H-吡喃-3-羧酸盐以及3,4-二取代的异噁唑-5(4H)-酮，采用了氢钾邻苯二甲酸盐（KHP）作为廉价的商业可得催化剂，得到了高产率。研究发现，这种三组分串联反应使得在50°C的水相中合成了吡喃环接合的杂环化合物。3,4-二取代的异噁唑-5(4H)-酮是在室温下使用10 mol% KHP水相合成的。此外，在存在5 mol% KHP的情况下，采用含亚甲基的化合物（如马来腈或乙基氰乙酸酯）与芳香醛的反应，得到了α,β-不饱和腈。该方法是一种简单易行的合成多种吡喃环接合化合物、含异噁唑-5(4H)-酮的杂环化合物和Knoevenagel加成物的直截了当的方法。该反应安全、条件温和且环境友好。其他显著优点包括催化剂的重复使用、不使用有害有机溶剂以及简便的后处理。
• One-pot three-component reaction for the synthesis of pyran annulated heterocyclic compounds using DMAP as a catalyst
  作者：Abu T. Khan、Mohan Lal、Shahzad Ali、Md. Musawwer Khan

  DOI：10.1016/j.tetlet.2011.08.019

  日期：2011.10

  The one-pot three-component reaction for the synthesis of pyran annulated heterocycles is reported by condensing aromatic aldehydes, ethyl cyanoacetate, or malononitrile and C–H activated acidic compounds in the presence of catalytic amount of 4-(dimethylamino)pyridine (DMAP) in ethanol under reflux conditions. The significant features of the present protocol are simple, environmentally benign, high

  据报道，在催化量的4-（二甲基氨基）吡啶（DMAP）存在下，芳族醛，氰基乙酸乙酯或丙二腈与CH活化的酸性化合物缩合，可生成吡喃环杂环的一锅三组分反应。在乙醇中回流条件下。本方案的显着特征是简单，对环境无害，高收率，非水后处理程序，无色谱分离和催化剂的可回收性。
• Practical and efficient synthesis of tetrahydrobenzo[b]pyran using caffeine supported on silica as an ionic liquid solid acid catalyst
  作者：Mohammad Bakherad、Ali Keivanloo、Elmira Moradian、Amir H. Amin、Rahele Doosti、Mahsa Armaghan

  DOI：10.1007/s13738-018-1468-y

  日期：2018.12

  The catalyst prepared was then characterized by the FT-IR spectroscopy, TGA, EDX, and SEM techniques. It was found that this heterogeneous catalyst was a highly efficient one for the synthesis of tetrahydrobenzo[b]pyrans in good-to-high yields, and could be recovered by a simple filtration of the reaction solution and reused for five consecutive runs. The attractive features of this method are simple

  新型催化剂二氧化硅-咖啡因硫酸氢盐[SiO 2 -caff。] HSO 4可以方便地由市售的3-氯丙基三乙氧基硅烷固定在二氧化硅上，然后与咖啡因反应制得。然后通过FT-IR光谱，TGA，EDX和SEM技术表征制备的催化剂。发现该非均相催化剂是用于以高至高收率合成四氢苯并[ b ]吡喃的高效催化剂，并且可以通过简单过滤反应溶液进行回收并将其重复使用五次。该方法的吸引人的特征是操作简单，反应干净，后处理容易，使用可重复使用的催化剂以及进行多组分反应。