4,6,6,10,10-pentamethyl-2H,6H,10H-benzo<1,2-b:3,4-b':5,6-b''>tripyran-2-one | 106726-20-9

• 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: 4,6,6,10,10-pentamethyl-2H,6H,10H-benzo<1,2-b:3,4-b':5,6-b''>tripyran-2-one
• 英文别名: 4-methyldipetalactone；4,6,6,10,10-pentamethyl-2H,6H,10H-dipyrano[2,3-f:2',3'-h]chromen-2-one；6,10,10,16,16-pentamethyl-3,9,15-trioxatetracyclo[12.4.0.02,7.08,13]octadeca-1,5,7,11,13,17-hexaen-4-one
• CAS: 106726-20-9
• 化学式: C₂₀H₂₀O₄
• 分子量: 324.376
• InChiKey: PHOMDVJSRNFSJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  4,4-二甲氧基-2-甲基-2-丁醇 、 5,7-二羟基-4-甲基香豆素 在 吡啶 作用下， 生成 4,6,6,10,10-pentamethyl-2H,6H,10H-benzo<1,2-b:3,4-b':5,6-b''>tripyran-2-one
  参考文献：
  名称：

  Structural and antivirial studies of dipetalactone and its methyl derivative

  摘要：

  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.

  DOI：

  10.1016/j.molstruc.2013.09.020

文献信息

• Anticancer effects of alloxanthoxyletin and fatty acids esters – In vitro study on cancer HTB-140 and A549 cells
  作者：Michał Jóźwiak、Marta Struga、Piotr Roszkowski、Agnieszka Filipek、Grażyna Nowicka、Wioletta Olejarz

  DOI：10.1016/j.biopha.2018.12.005

  日期：2019.2

  such as family of Rutaceae, and its synthetic derivatives show cytotoxic and antitumor activities. In the present study new eleven esters of alloxanthoxyletin and fatty acids were synthesized and evaluated for their anticancer toxicity. The structures of the compounds were confirmed by Proton Nuclear Magnetic Resonance (H NMR), Carbon-13 Nuclear Magnetic Resonance (C NMR) and High Resolution Mass Spectrometry

  别氧烷氧基letin是一种天然的吡喃香​​豆素，它是从芸苔科等多种植物中分离得到的，其合成衍生物具有细胞毒性和抗肿瘤活性。在本研究中，合成了新的十一种四氧杂环丁烷酯和脂肪酸酯，并评估了它们的抗癌毒性。化合物的结构通过质子核磁共振（1 H NMR），碳13核磁共振（13 C NMR）和高分辨率质谱（HRMS）分析确认。对于所有化合物，使用3-（4,5-二甲基噻唑基-2）-2,5-二苯基四唑溴化物（MTT）分析法测定对人黑素瘤细胞（HTB-140），人上皮性肺癌细胞（A549）的细胞毒性作用和人类角质形成细胞系（HaCaT）。对于活性最高的化合物（8-11），进行了乳酸脱氢酶（LDH）分析，以评估细胞损伤的水平以及迁移抑制分析。为了解释细胞死亡诱导的基本机理，在膜联蛋白V-FITC / 7-AAD流式细胞仪分析中研究了衍生物8-11对早期和晚期凋亡的影响。结果表明，与人角质形成细胞（HaCaT
• 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。
• Zawadowski, Teodor; Mazur, Andrzej; Kleps, Jerzy, Polish Journal of Chemistry, 1985, vol. 59, # 5-6, p. 547 - 552
  作者：Zawadowski, Teodor、Mazur, Andrzej、Kleps, Jerzy

  DOI：——

  日期：——