2-amino-4-(4-chlorophenyl)-5-oxo-4,5,6,7-tetrahydrocyclopenta[b]pyran-3-carbonitrile | 1338246-47-1

• 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: 2-amino-4-(4-chlorophenyl)-5-oxo-4,5,6,7-tetrahydrocyclopenta[b]pyran-3-carbonitrile
• 英文别名: 2-amino-4-(4-chlorophenyl)-5-oxo-6,7-dihydro-4H-cyclopenta[b]pyran-3-carbonitrile
• CAS: 1338246-47-1
• 化学式: C₁₅H₁₁ClN₂O₂
• 分子量: 286.718
• InChiKey: FIZDDFDUJQTAQP-UHFFFAOYSA-N

物化性质

• 熔点：
  216-218 °C
• 沸点：
  561.7±50.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,3-环戊二酮 、 4-氯苯甲醛 、 丙二腈 在 4-二甲氨基吡啶 作用下， 以 乙醇 为溶剂， 反应 0.17h， 以98%的产率得到2-amino-4-(4-chlorophenyl)-5-oxo-4,5,6,7-tetrahydrocyclopenta[b]pyran-3-carbonitrile
  参考文献：
  名称：

  以DMAP为催化剂的一锅三组分反应合成吡喃环杂环化合物

  摘要：

  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。

  DOI：

  10.1016/j.tetlet.2011.08.019

文献信息

• Multicomponent domino reactions: borax catalyzed synthesis of highly functionalised pyran-annulated heterocycles
  作者：Aniruddha Molla、Ezaz Hossain、Sahid Hussain

  DOI：10.1039/c3ra43514h

  日期：——

  A collection of pyrano[3,2-c] chromene, 4H-chromene and 4H-pyran were synthesized in excellent yield employing an innocuous, inexpensive and naturally occurring borax-catalyzed multicomponent domino reaction. The present protocol offers advantages in terms of higher yields, short reactions time and no workup and no column chromatography.

  利用一种无害、廉价和天然存在的硼砂催化多组分多米诺反应，合成了一系列吡喃并[3,2-c] 色烯、4H-色烯和 4H-吡喃，收率极高。本方案具有产率高、反应时间短、无需操作和柱层析等优点。
• 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。
• Meglumine: A Novel and Efficient Catalyst for One-Pot, Three-Component Combinatorial Synthesis of Functionalized 2-Amino-4<i>H</i>-pyrans
  作者：Rui-Yun Guo、Zhi-Min An、Li-Ping Mo、Rui-Zhi Wang、Hong-Xia Liu、Shu-Xia Wang、Zhan-Hui Zhang

  DOI：10.1021/co400107j

  日期：2013.11.11

  An efficient one-pot synthesis of functionalized 2-amino-4H-pyrans by a meglumine-catalyzed three-component reaction has been developed. A broad range of substrates including aromatic and heteroaromatic aldehydes, isatin derivatives, and acenaphthenequinone are condensed with enolizable C-H activated compounds and alkylmalonates to give the desired products in high to excellent yields. This methodology provides an alternative approach for rapid access to construct a diversity-oriented library of 4H-pyrans.
• Nickel Nanoparticles as Semiheterogeneous Catalyst for One-Pot, Three-Component Synthesis of 2-Amino-4<i>H</i>-pyrans and Pyran Annulated Heterocyclic Moieties
  作者：Jitender M. Khurana、Kanika Vij

  DOI：10.1080/00397911.2012.700474

  日期：2013.9.2

  An efficient route for the synthesis of 2-amino-4H-pyrans and pyran annulated heterocyclic moieties has been reported via one-pot tandem Knoevenagel-cyclocondensation of aldehydes, malononitrile, and carbocyclic/heterocyclic 1,3-diones in the presence of stabilized nickel nanoparticles in ethylene glycol at room temperature. A wide range of aromatic aldehydes undergo the condensation readily to afford the pharmacologically important compounds in excellent yields. Bis-pyranization has been observed in the reactions of terephthaldehyde. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.
• 1,8-Diazabicyclo[5.4.0]undec-7-ene: A Highly Efficient Catalyst for One-Pot Synthesis of Substituted Tetrahydro-4<i>H</i>-chromenes, Tetrahydro[<i>b</i>]pyrans, Pyrano[<i>d</i>]pyrimidines, and 4<i>H</i>-Pyrans in Aqueous Medium
  作者：Jitender M. Khurana、Bhaskara Nand、Pooja Saluja

  DOI：10.1002/jhet.1507

  日期：2014.5

  We have reported 1,8‐diazabicyclo[5.4.0]undec‐7‐ene catalyzed one‐pot synthesis of tetrahydro‐4H‐chromenes, tetrahydro[b]pyrans, pyrano[d]pyrimidines and 4H‐pyrans from aldehydes, active methylene compounds malononitrile/ethyl cyanocacetate and activated C–H acids such as dimedone, 1,3‐cyclohexanedione, 1,3‐cyclopentanedione, 1,3‐dimethylbarbituric acid, and ethyl acetoacetate in water under reflux

  我们已经报道了1,8-二氮杂双环[5.4.0]十一碳-7烯从醛催化一锅合成四氢-4 H-苯甲基，四氢[ b ]吡喃，吡喃并[ d ]嘧啶和4 H-吡喃。活性亚甲基化合物丙二腈/氰基乙酸乙酯和活化的C-H酸，如二甲酮，1,3-环己二酮，1,3-环戊烷二酮，1,3-二甲基巴比妥酸和乙酰乙酸乙酯在水中回流。该方法的吸引人的特征是温和的反应条件，反应介质的可重​​复使用性，较短的反应时间，易于分离的产物以及优异的产率。版权所有©2013 HeteroCorporation