4-methyl-8-phenyl-8,9-dihydropyrano[2,3-f]chromene-2,10-dione | 102145-67-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 4-methyl-8-phenyl-8,9-dihydropyrano[2,3-f]chromene-2,10-dione
• CAS: 102145-67-5
• 化学式: C₁₉H₁₄O₄
• 分子量: 306.318
• InChiKey: UIXNMVRUNDWEGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methyl-8-phenyl-8,9-dihydropyrano[2,3-f]chromene-2,10-dione 在 四(三苯基膦)钯 、 sodium carbonate 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.16h， 生成 10-(4-chlorophenyl)-4-methyl-2-oxo-8-phenyl-2,8-dihydropyrano[2,3-f]chromene-9-carbaldehyde
  参考文献：
  名称：

  Microwave-assisted synthesis of 10-aryl-4-methyl-2-oxo-8-phenyl-2,8-dihydropyrano[2,3-f]chromene-9-carbaldehydes by Suzuki coupling and their antimicrobial activity

  摘要：

  A series of new pyranochromenes has been synthesized by conventional and microwave irradiation methods from 10-chloro-4-methyl-2-oxo-8-phenyl-2,8-dihydropyrano[2,3-f]chromene-9-carbaldehyde using the Suzuki coupling. All the synthesized compounds were characterized by standard spectroscopic methods and elemental analysis and screened for their antibacterial and antifungal activities.

  DOI：

  10.1007/s10593-015-1719-0
• 作为产物：
  描述：

  8-乙酰基-7-羟基-4-甲基-2H-1-苯并吡喃-2-酮 在 sodium hydroxide 、 silica gel 作用下， 以 甲醇 为溶剂， 反应 54.0h， 生成 4-methyl-8-phenyl-8,9-dihydropyrano[2,3-f]chromene-2,10-dione
  参考文献：
  名称：

  Sangwan, Naresh K.; Verma, Braham S.; Dhindsa, Kuldip Singh, Journal fur praktische Chemie (Leipzig 1954), 1988, vol. 330, # 1, p. 137 - 141

  摘要：

  DOI：

文献信息

• Synthesis and antiproliferative and c-Src kinase inhibitory activities of cinnamoyl- and pyranochromen-2-one derivatives
  作者：Karam Chand、Amir Nasrolahi Shirazi、Preeti Yadav、Rakesh K. Tiwari、Meena Kumari、Keykavous Parang、Sunil K. Sharma

  DOI：10.1139/cjc-2013-0053

  日期：2013.8

  8-cinnamoylchromen-2-one and dihydropyranochromen-2-one derivatives were synthesized and their antiproliferative activities were evaluated against three human cancer cell lines, i.e., ovarian adenocarcinoma (SK-OV-3), leukemia (CCRF-CEM), and breast carcinoma (MCF-7). In general, 8-cinnamoylchromen-2-one derivatives were found to have higher antiproliferative activity against the cancer cells when compared with

  合成了一系列 6- 和 8-cinnamoylchromen-2-one 和 dihydropyranochromen-2-one 衍生物，并评估了它们对三种人类癌细胞系的抗增殖活性，即卵巢腺癌 (SK-OV-3)、白血病 (CCRF) -CEM) 和乳腺癌 (MCF-7)。一般而言，与 6-肉桂酰类似物相比，8-cinnamoylchromen-2-one 衍生物对癌细胞具有更高的抗增殖活性。在所有杂合 chromen-2-one - 查尔酮/黄烷酮化合物中，发现 7-hydroxy-8-cinnamoylchromen-2-one 衍生物 35 对所有癌细胞系均具有持续活性并抑制 SK-的细胞增殖OV-3、CCRF-CEM 和 MCF-7 在孵育 72 小时后浓度为 50 μmol/L 时分别增加 63%、50% 和 43%。该化合物还表现出最高的 Src 激酶抑制 (IC50 = 14
• Khan, M. S. Y.; Sharma, Poonam, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 3, p. 374 - 376
  作者：Khan, M. S. Y.、Sharma, Poonam

  DOI：——

  日期：——
• Microwave-assisted synthesis of 8-aryl-10-chloro-4-methyl-2-oxo-2,8-dihydropyrano[2,3-f]chromene-9-carbaldehydes and their antimicrobial activity
  作者：D. Ashok、B. Vijaya Lakshmi、Arram Ganesh、S. Ravi、S. Adam、S. D. S. Murthy

  DOI：10.1134/s1070363214110322

  日期：2014.11

  A series of new coumarin-chromene hybrids have been synthesized by conventional and microwave irradiation methods from 8-aryl-4-methyl-8,9-dihydropyrano[2,3-f]chromene-2,10-diones using the Vilsmeier-Haack reagent. All the synthesized compounds were characterized by IR, H-1 NMR, C-13 NMR, MS, and elemental analyses and were screened for antibacterial and antifungal activity. Among the compounds tested, methoxy-substituted pyranochromenones revealed the best antimicrobial profile.
• SANGWAN, NARESH K.;VERMA, BRAHAM S.;DHINDSA, KULDIP SINGH, J. PRAKT. CHEM., 330,(1988) N 1, 137-141
  作者：SANGWAN, NARESH K.、VERMA, BRAHAM S.、DHINDSA, KULDIP SINGH

  DOI：——

  日期：——