9-(biphenyl-4-yl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione | 324009-63-4

• 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: 9-(biphenyl-4-yl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione
• 英文别名: 9-(4-phenylphenyl)-3,4,5,6,7,9-hexahydro-2H-xanthene-1,8-dione
• CAS: 324009-63-4
• 化学式: C₂₅H₂₂O₃
• mdl: MFCD00809819
• 分子量: 370.448
• InChiKey: SALIOUFSLBPJAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-(biphenyl-4-yl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione 在 氯磺酸 作用下， 生成 4'-(1,8-Dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)-biphenyl-4-sulfonyl chloride
  参考文献：
  名称：

  CHLOROSULFONATION OF 9-ARYLOCTAHYDROXANTHEN-1,8-DIONES

  摘要：

  The 9-aryloctathydroxanthen-1,8-diones (3, 4-24) were prepared by reaction of cyclohexan-1,3-dione (1) with selected arylaldehydes. The xanthendiones (4-9, 11, 12, 18, 21, 22) were successfully reacted with chlorosulfonic acid, and the crude sulfonyl chlorides were converted into 15 sulfonamides (26-40) for screening as potential pesticides. Attempted chlorosulfonation of the xanthendiones (13-17) was unsuccessful. alpha-Methylcinnamaldehyde was reacted with cyclohexandione (1) to yield the corresponding xanthendione derivative (23). On the other hand, with o-methoxycinnamaldehyde an impure product formed and the p-methoxy isomer afforded the corresponding 2-arylpyran (25). The NMR spectral data of the compounds are briefly discussed.

  DOI：

  10.1080/10426500490494741
• 作为产物：
  描述：

  在 盐酸 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 9-(biphenyl-4-yl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione
  参考文献：
  名称：

  CHLOROSULFONATION OF 9-ARYLOCTAHYDROXANTHEN-1,8-DIONES

  摘要：

  The 9-aryloctathydroxanthen-1,8-diones (3, 4-24) were prepared by reaction of cyclohexan-1,3-dione (1) with selected arylaldehydes. The xanthendiones (4-9, 11, 12, 18, 21, 22) were successfully reacted with chlorosulfonic acid, and the crude sulfonyl chlorides were converted into 15 sulfonamides (26-40) for screening as potential pesticides. Attempted chlorosulfonation of the xanthendiones (13-17) was unsuccessful. alpha-Methylcinnamaldehyde was reacted with cyclohexandione (1) to yield the corresponding xanthendione derivative (23). On the other hand, with o-methoxycinnamaldehyde an impure product formed and the p-methoxy isomer afforded the corresponding 2-arylpyran (25). The NMR spectral data of the compounds are briefly discussed.

  DOI：

  10.1080/10426500490494741

文献信息

• Microwave-assisted clean synthesis of xanthenes and chromenes in [bmim][PF6] and their antioxidant studies
  作者：P. Iniyavan、S. Sarveswari、V. Vijayakumar

  DOI：10.1007/s11164-014-1821-4

  日期：2015.10

  An efficient one-pot synthesis of xanthene and chromene derivatives by three-component reactions of aryl aldehydes, cyclic 1,3-diketones, and 2-naphthol/4-hydroxy coumarin catalyzed by ionic liquid (IL) [bmim][PF6] under microwave irradiation is described. The present scheme provides several advantages such as short reaction time, mild reaction conditions, good yields, convenient operation, and reuse

  离子液体（IL）催化芳基醛，环状1,3-二酮和2-萘酚/ 4-羟基香豆素的三组分反应有效地一锅合成x吨和色烯衍生物[bmim] [PF 6 ]描述了在微波照射下。本方案具有几个优点，例如反应时间短，反应条件温和，产率高，操作方便和IL的重复使用。通过DPPH方法评估了合成化合物的体外抗氧化活性。化合物 6a，6h，6c，6b，4k 和 4a 显示出最高的抗氧化剂效能。
• Facile and efficient synthesis of xanthenedione derivatives promoted by niobium pentachloride
  作者：Willian H. dos Santos、Luiz C. Da Silva-Filho

  DOI：10.1515/chempap-2016-0098

  日期：2016.1.1

  Xanthenedione derivatives were synthesised in one-pot reactions between arylaldehyde derivatives and 1,3-cyclohexanedione promoted by niobium pentachloride. This new method is simple, costeffective, high-yielding with a good variety of substrates generality, and can be conducted within reasonable reaction times.

  五氧化二铌衍生物是通过芳基醛衍生物与五氯化铌促进的1,3-环己二酮之间的一锅反应合成的。这种新方法简单，经济高效，产率高，具有多种底物通用性，并且可以在合理的反应时间内进行。