3,4,9,10-tetrahydro-2,2,8,8-tetramethyl-2H,8H-benzo<1,2-b; 3,4-b'>dipyran | 78968-62-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3,4,9,10-tetrahydro-2,2,8,8-tetramethyl-2H,8H-benzo<1,2-b; 3,4-b'>dipyran
• 英文别名: 6-acetyl-2,2,8,8-tetramethyl-3,4,9,10-tetrahydro-2H,8H-benzo<1,2-b:3,4-b'>dipyran；1-(2,2,8,8-tetramethyl-2,3,4,8,9,10hexahydroxypyrano[2,3-f]chromen-6-yl)ethanone；1-(2,2,8,8-Tetramethyl-3,4,9,10-tetrahydropyrano[2,3-f]chromen-6-yl)ethanone
• CAS: 78968-62-4
• 化学式: C₁₈H₂₄O₃
• 分子量: 288.387
• InChiKey: BFUGLVQJRDQAFF-UHFFFAOYSA-N

物化性质

• 熔点：
  76 °C
• 沸点：
  426.9±45.0 °C(Predicted)
• 密度：
  1.054±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4,9,10-tetrahydro-2,2,8,8-tetramethyl-2H,8H-benzo<1,2-b; 3,4-b'>dipyran 在 溴 作用下， 以 四氯化碳 、 乙醇 为溶剂， 生成 4-(2,2,8,8-tetramethyl-3,4,9,10-tetrahydropyrano[2,3-f]chromen-6-yl)-1,3-thiazol-2-amine
  参考文献：
  名称：

  Ahluwalia, V. K.; Arora, K. K.; Kaur, Gurvinder, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 556 - 558

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4-二羟基苯乙酮 、 2-甲基-3-丁烯-2-醇 在 polyphosphoric acid 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以68%的产率得到3,4,9,10-tetrahydro-2,2,8,8-tetramethyl-2H,8H-benzo<1,2-b; 3,4-b'>dipyran
  参考文献：
  名称：

  Synthesis, structure activity relationship and mode of action of 3-substitutedphenyl-1-(2,2,8,8-tetramethyl-3,4,9,10-tetrahydro-2 H ,8 H -pyrano[2,3- f ]chromen-6-yl)-propenones as novel anticancer agents in human leukaemia HL-60 cells

  摘要：

  A novel class of 3-substitutedphenyl-1-(2,2,8,8-tetramethyl-3,4,9,10-tetrahydro-2H,8H-pyrano[2,3-f]chromen-6-yl)-propenones were designed, synthesized and evaluated for their antiproliferative activity against the human cancer cell lines of diverse origin. Structure activity relationship was elucidated with various substitutions on the benzene ring and these variations significantly affected the potency. Most of the twelve tested compounds inhibited the growth of aggressive cancer cell lines. Moreover, three compounds 4j, 4k and 41 displayed excellent cytotoxic profile by inhibiting >90% cell proliferation in HL-60 and Caco-2 cells at 50 mu M concentration. Further studies to elucidate the mode of action revealed that these three compounds induced G0/G1 cell cycle arrest and apoptosis, which was accompanied by loss of mitochondrial membrane potential, DNA fragmentation and nuclear morphology in HL-60 cells. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.027

文献信息

• Bi(OTf)3-catalysed prenylation of electron-rich aryl ethers and phenols with isoprene: a direct route to prenylated derivatives
  作者：Katie E. Judd、Lorenzo Caggiano

  DOI：10.1039/c1ob05365e

  日期：——

  Electron-rich aryl ethers and phenols react with isoprene (2-methylbuta-1,3-diene) in the presence of catalytic Bi(OTf)3 at 40 °C to afford the corresponding prenylated or 2,2-dimethylchroman products, respectively, in moderate to good yields. This transformation offers a convenient and expedient entry to prenylated derivatives of electron-rich aromatics that often display enhanced biological activities

  富含电子的芳基醚和酚与 异戊二烯 （2-甲基丁-1,3-二烯）在40°C下存在催化Bi（OTf）3的情况下提供相应的烯丙基化或2,2-二甲基苯并吡喃产品分别以中等到良好的产量。这种转变为通常显示出增强的生物活性的富含电子的芳族化合物的烯丙基化衍生物的进入提供了方便和便利的途径。该方法已用于生物活性天然产物和相关化合物的有效合成中。
• Nuclear isoprenylation of polyhydroxyacetophenones
  作者：V.K. Ahluwalia、K.K. Arora

  DOI：10.1016/s0040-4020(01)92463-9

  日期：1981.1

  A novel method of nuclear isoprenylation leading to the exclusive formation of 2,2-dimethylchromans has been achieved by the direct condensation of polyhydroxyacetophenones with isoprene in presence of phosphoric acid. Acetylchromans, thus obtained, are dehydrogenated with DDQ to given corresponding 2,2-dimethylchromenes. Using this method, synthesis of number of naturally occurring chromenes, viz

  通过在磷酸的存在下聚羟基苯乙酮与异戊二烯的直​​接缩合，已经实现了导致异戊二烯仅形成2,2-二甲基苯并二氢吡喃的新型核异戊烯化方法。将如此获得的乙酰基苯并二氢吡喃酮用DDQ脱氢，得到相应的2，2-二甲基苯并二苯甲基。使用这种方法，可以合成许多天然存在的色烯。ripariochromene A（6），eupatoriochromene（10），encecalin（11），isoevodionol（16），evodionol（17）和甲基evodionol（18）已受影响。
• Murthy; Nanda, Rani; Kumar, K. Ravi, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 2, p. 532 - 534
  作者：Murthy、Nanda, Rani、Kumar, K. Ravi、Swamy

  DOI：——

  日期：——
• Ahluwalia, Vinod Kumar; Arora, Krishan Kumar; Jolly, Ravinder Singh, Heterocycles, 1981, vol. 16, # 12, p. 2155 - 2157
  作者：Ahluwalia, Vinod Kumar、Arora, Krishan Kumar、Jolly, Ravinder Singh

  DOI：——

  日期：——
• AHLUWALIA V. K.; ARORA K. K.; KAUR GURVINDER, INDIAN J. CHEM., 25,(1986) N 5, 556-558
  作者：AHLUWALIA V. K.、 ARORA K. K.、 KAUR GURVINDER

  DOI：——

  日期：——