2-amino-4-(5-chloro-2-thienyl)-7-methyl-5-oxo-4H,5Hpyrano[4,3-b]pyran-3-carbonitrile | 919749-03-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2-amino-4-(5-chloro-2-thienyl)-7-methyl-5-oxo-4H,5Hpyrano[4,3-b]pyran-3-carbonitrile
• 英文别名: 2-amino-4-(5-chlorothiophen-2-yl)-7-methyl-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carbonitrile；2-amino-4-(5-chlorothiophen-2-yl)-7-methyl-5-oxo-4H-pyrano[3,2-c]pyran-3-carbonitrile
• CAS: 919749-03-4
• 化学式: C₁₄H₉ClN₂O₃S
• 分子量: 320.756
• InChiKey: LIEITAIFBIIEEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-氯噻吩-2-甲醛 、 4-羟基-6-甲基-2-吡喃酮 、 丙二腈 在 nano cellulose OBF₂ 作用下， 以 乙醇 为溶剂， 反应 0.42h， 以86%的产率得到2-amino-4-(5-chloro-2-thienyl)-7-methyl-5-oxo-4H,5Hpyrano[4,3-b]pyran-3-carbonitrile
  参考文献：
  名称：

  Nano-cell-OBF 2：一种在温和绿色条件下一锅合成吡喃并[4,3- b ]吡喃的高效廉价催化剂

  摘要：

  以三氟化硼为路易斯酸，纳米纤维素为载体，制备了新合成的纳米电池-OBF 2催化剂。使用傅立叶变换红外光谱（FTIR），场发射扫描电子显微镜（FE-SEM）和能量色散X射线光谱（EDX）技术对获得的新型纳米结构进行了评估。另外，通过热分析技术（TGA / DTG）研究了纳米纤维素和纳米细胞-OBF 2的分解步骤和热稳定性。已在温和的反应条件下，在芳香族醛，4-羟基-6-甲基-2 H-吡喃-2-酮和丙二腈的一锅三组分缩合反应中有效检测了固体酸催化剂的活性，从而得到吡喃[4,3- b吡喃衍生物，收率高至优异。

  DOI：

  10.1080/24701556.2019.1603159

文献信息

• Solvent-free, green and efficient synthesis of pyrano[4, 3-b]pyrans by grinding and their biological evaluation as antitumor and antioxidant agents
  作者：Deepika Rajguru、Balwant S. Keshwal、Shubha Jain

  DOI：10.1007/s00044-013-0586-4

  日期：2013.12

  A facile, green, and efficient method has been developed for the synthesis of pyrano[4, 3-b]pyrans via a one-pot reaction of aromatic aldehydes, malononitrile, and 4-hydroxy-6-methyl-pyran-2-one in the presence of ammonium acetate under solvent-free conditions using grinding method. The experimental simplicity, short reaction time, easy work-up, avoidance of organic solvents, and utilization of an inexpensive and readily available catalyst make this new methodology practical and economically attractive. The antitumor activity of the compounds was tested against human breast cancer cell line MCF-7. Compounds 4l, 4o, and 4p showed good cytotoxic activity comparable with standard drug Doxorubicin. On the other hand, compounds 4q and 4r exhibited potent growth inhibitory activity. Furthermore, the synthesized compounds were screened for in vitro antioxidant activity by DPPH assay. All the compounds assayed showed moderate to good free radical scavenging activity.
• Alum [KAl(SO4)2·12H2O]: a green and efficient catalyst for synthesis of pyrano[4,3-b]pyrans in water under conventional and microwave conditions
  作者：Deepika Rajguru、Balwant S. Keshwal、Shubha Jain、Vasant W. Bhagwat

  DOI：10.1007/s00706-013-0975-x

  日期：2013.9

  One-pot synthesis of pyrano[4,3-b]pyrans by condensation of 4-hydroxy-6-methylpyran-2-one, aromatic aldehydes, and malononitrile or cyanoacetates in water using alum as a non-toxic, readily available, and reusable catalyst at 80 A degrees C under conventional conditions and also under microwave irradiation is described.
• H6P2W18O62·18H2O: A green and reusable catalyst for one-pot synthesis of pyrano[4,3-b]pyrans in water
  作者：Deepika Rajguru、Balwant S. Keshwal、Shubha Jain

  DOI：10.1016/j.cclet.2013.07.010

  日期：2013.11

  A convenient, efficient and environmentally benign procedure has been developed for the synthesis of pyrano[4,3-b]pyran derivatives via a one-pot, three-component reaction of 4-hydroxy-6-methylpyran-2-one, aldehydes and malononitrile in water using H6P2W18O62 center dot 18H(2)O as catalyst. Reusability of the catalyst and reaction media, short reaction times and easy isolation of products are some added advantages of the present methodology. (C) 2013 Balwant S. Keshwal. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
• Nano-cell-OBF₂: an efficient and cheap catalyst for one-pot synthesis of pyrano[4,3-<i>b</i>]pyrans under mild and green condition
  作者：Saeed Mousavi Khatat、Bahareh Sadeghi、Maryam Ghasemi

  DOI：10.1080/24701556.2019.1603159

  日期：2019.2

  nano-cell-OBF2 were investigated by thermal analysis techniques (TGA/DTG). The activity of solid acid catalyst has been effectively inspected in a one-pot, three-component condensation reaction of aromatic aldehydes, 4-hydroxy-6-methyl-2H-pyran-2-one and malononitrile under mild reaction conditions to afford pyrano [4,3-b] pyran derivatives in good to excellent yields.

  以三氟化硼为路易斯酸，纳米纤维素为载体，制备了新合成的纳米电池-OBF 2催化剂。使用傅立叶变换红外光谱（FTIR），场发射扫描电子显微镜（FE-SEM）和能量色散X射线光谱（EDX）技术对获得的新型纳米结构进行了评估。另外，通过热分析技术（TGA / DTG）研究了纳米纤维素和纳米细胞-OBF 2的分解步骤和热稳定性。已在温和的反应条件下，在芳香族醛，4-羟基-6-甲基-2 H-吡喃-2-酮和丙二腈的一锅三组分缩合反应中有效检测了固体酸催化剂的活性，从而得到吡喃[4,3- b吡喃衍生物，收率高至优异。