6,6,10,10-tetramethyl-2H,6H,10H-benzo<1,2-b:13,4-b':5,6-b''>tripyran-2-one | 57601-61-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 6,6,10,10-tetramethyl-2H,6H,10H-benzo<1,2-b:13,4-b':5,6-b''>tripyran-2-one
• 英文别名: 6,6,10,10-tetramethyl-6,10-dihydro-2H-dipyrano[2,3-f:2',3'-h]chromen-2-one；6,6,10,10-tetramethyl-2H,6H,10H-dipyrano[2,3-f:2',3'-h]chromen-2-one；(6,6,10,10-tetramethyl-6H,10H-dipyrano[2,3-f;2',3'-h]coumarin)；dipetalolactone；dipetalactone；6,6,10,10-tetramethyl-6H,10H-dipyrano[2,3-f;2',3'-h]chromen-2-one；10,10,16,16-tetramethyl-3,9,15-trioxatetracyclo[12.4.0.02,7.08,13]octadeca-1(14),2(7),5,8(13),11,17-hexaen-4-one
• CAS: 57601-61-3
• 化学式: C₁₉H₁₈O₄
• 分子量: 310.35
• InChiKey: BHLCTWNBGOOKAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 sodium hydroxide 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 水 为溶剂， 反应 19.0h， 生成 6,6,10,10-tetramethyl-2H,6H,10H-benzo<1,2-b:13,4-b':5,6-b''>tripyran-2-one
  参考文献：
  名称：

  Fremy 的盐介导的氧化加成。天然二萜内酯全合成及其免疫调节活性的新方法

  摘要：

  天然双吡喃香豆素二戊内酯的结构已通过间苯二酚的明确合成路线得到证实。该序列由引入 3-氯-3-甲基丁-1-炔部分的吡喃环形成步骤引发。然后，预期产物经过 Fremy's 盐调节的氧化加成，然后闭环以产生双戊内酯。还发现双瓣内酯在携带 S180 的小鼠癌细胞系中具有免疫活性。

  DOI：

  10.3390/molecules180911485

文献信息

• Synthesis and Cytotoxicity of Coumarin Derivatives and Nordentatin
  作者：Pawantree Promsuwan、Chavi Yenjai

  DOI：10.14233/ajchem.2013.13687

  日期：——

  Nordentatin and 10 coumarin derivatives were synthesized and evaluated for cytotoxicity. Compounds 6, 7, 9 and 13 showed cytotoxicity against the NCI-H187 cell line with IC50 value ranging of 3-7 μg/mL. Among synthesized coumarins, compounds 4 and 13 demonstrated cytotoxicity against the KB cell line with IC50 values of 3.94 and 6.44 μg/mL, respectively. Fortunately, coumarins 4 and 7 may be one of the new lead compounds for the development of anticancer agents due to reason that they showed weak and inactive against normal cells.

  合成了Nordentatin和10种香豆素衍生物并对其细胞毒性进行了评估。化合物6、7、9和13对NCI-H187细胞系表现出细胞毒性，IC50值在3-7 μg/mL范围内。在合成的香豆素中，化合物4和13对KB细胞系显示出细胞毒性，分别为3.94和6.44 μg/mL的IC50值。幸运的是，由于香豆素4和7对正常细胞表现出微弱的活性或无活性，它们可能成为开发抗癌药物的新型先导化合物之一。
• One‐pot Synthesis of Fused Dipyranocoumarins from Dihydroxycoumarins and Propargyl Chlorides under Microwave Irradiation
  作者：Evangelia‐Eirini N. Vlachou、Catherine Gabriel、Konstantinos E. Litinas

  DOI：10.1002/jhet.3376

  日期：2019.1

  Dipetalolactone and 4‐methyldipetalolactone are prepared in excellent yield by a one‐pot tandem propargylation/Claisen rearrangement/cyclization reaction of the corresponding 5,7‐dihydroxycoumarins with 3‐chloro‐3‐methylbut‐1‐yne in the presence of Cs2CO3 under microwave irradiation. The analogous reactions of propargyl chloride with esculetins or 5,7‐dihydroxycoumarins led to dipropargyloxy derivatives

  在Cs 2 CO存在的情况下，通过相应的5,7-二羟基香豆素与3-氯-3-甲基丁-1-炔的一锅串联串联炔丙基化/克莱森重排/环化反应，可以以高收率制得双荆芥内酯和4-甲基双荆芥内酯3.在微波照射下。炔丙基氯与七叶皂苷或5,7-二羟基香豆素的类似反应可生成二炔丙基氧基衍生物。后者通过用负载在TiO 2或BF 3 .Et 2 O中的N，N上的金纳米颗粒处理微波辐照下的二甲基甲酰胺（DMF）对相应的稠合双吡喃香豆素具有非常好至极好的收率。七叶红素与3-氯-3-甲基丁-1-炔的反应主要产生环己烯基稠合的二恶英[g]香豆素。
• A One-Pot Synthesis of Pyranocoumarins Through Microwave-Promoted Propargyl Claisen Rearrangement/Wittig Olefination
  作者：Bernd Schmidt、Christiane Schultze

  DOI：10.1002/ejoc.201701684

  日期：2018.1.17

  A method towards the synthesis of angular pyranocoumarins from propargylic ethers has been developed. The sequence proceeds through a microwave‐promoted tandem propargyl Claisen rearrangement, Wittig olefination, E/Z isomerization, and cyclization series of reactions in times as low as 10 min.

  已经开发了一种从炔丙基醚合成角吡喃香豆素的方法。该序列通过微波促进的串联炔丙基Claisen重排，Wittig烯烃化，E / Z异构化和环化反应系列进行，时间低至10分钟。
• Natural and Synthetic 2,2-Dimethylpyranocoumarins with Antibacterial Activity
  作者：Eleni Melliou、Prokopios Magiatis、Sofia Mitaku、Alexios-Leandros Skaltsounis、Efrosini Chinou、Ioanna Chinou

  DOI：10.1021/np0497447

  日期：2005.1.1

  A new efficient synthetic approach to the natural coumarins 5-hydroxyseselin (5), 5-methoxyseselin (3), and (+/-) cis-grandmarin (9) is described as well as the synthesis of some new derivatives in the 5-methoxyseselin series (10-15). The natural coumarins 7-hydroxyalloxanthyletin (6), alloxanthoxyletin (8), and dipetalolactone (7) have also been obtained as secondary products. The type of fusion of the pyrano ring in all cases has been established by 2D NMR spectroscopy. The compounds have been studied for their in vitro antibacterial activity, which has been compared with that of some previously synthesized seselin derivatives. The most active compounds were 3, 7, 8, 11, and 14. Some structure-activity relationships are discussed.
• Structural and antivirial studies of dipetalactone and its methyl derivative
  作者：Aleksandra Drzewiecka、Anna E. Koziol、Piotr Borowski、Giuseppina Sanna、Gabriele Giliberti、Paolo La Colla、Teodor Zawadowski、Marta Struga

  DOI：10.1016/j.molstruc.2013.09.020

  日期：2013.12

  Dipetalactone (6,6,10,10-tetramethyl-6H,10H-dipyranocoumarin) and its C4-methyl derivative have been synthesized and structurally studied. The structures of these compounds, explored on the basis of 1D and 2D NMR techniques in solution and the DFT/B3LYP calculations for the single molecule of dipetalactone, are in good agreement with those found in the crystals. In the tetracyclic dipetalactones the central coumarin ring systems are nearly planar and the pyran rings adopt a distorted sofa conformation.Both compounds crystallize with two symmetry independent molecules, A and B. The pi-stacking is the main force stabilizing the pairs of centrosymmetric dimers, A.A and B.B. These dimers interact via the intermolecular C-H center dot center dot center dot O and C-H center dot center dot center dot pi hydrogen bonds forming three-dimensional supramolecular frameworks which are nearly isostructural. The MP2 calculations reveal that the dimers of dipetalactone only slightly distort during the crystal formation as compared with those in the gas phase. The energy increase upon such a distortion was estimated as ca. 4 kcal mol(-1). In addition, the binding energy for the dimer was found to be ca. 20 kcal mol(-1).Dipetalactone and its methyl derivative were examined for cytotoxicity as well as anti-HIV activity. (C) 2013 Elsevier B.V. All rights reserved.