6-allyl-7-hydroxy-4-methyl-2H-1-benzopyran-2-one | 1616-53-1

• 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-allyl-7-hydroxy-4-methyl-2H-1-benzopyran-2-one
• 英文别名: 6-allyl-7-hydroxy-4-methyl-2H-chromen-2-one；4-methyl-7-hydroxy-6-allyloxycoumarin；6-allyl-7-hydroxy-4-methyl-chromen-2-one；6-Allyl-7-hydroxy-4-methyl-cumarin；6-Allyl-7-hydroxy-4-methylcumarin；7-Hydroxy-4-methyl-6-(prop-2-en-1-yl)-2H-1-benzopyran-2-one；7-hydroxy-4-methyl-6-prop-2-enylchromen-2-one
• CAS: 1616-53-1
• 化学式: C₁₃H₁₂O₃
• 分子量: 216.236
• InChiKey: TYZLFMHVFBADED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-allyl-7-hydroxy-4-methyl-2H-1-benzopyran-2-one 在 氢氧化钾 、 溴 作用下， 以 乙醇 、 乙酸酐 、 溶剂黄146 为溶剂， 反应 3.33h， 生成 4,5-二甲基补骨脂素
  参考文献：
  名称：

  Rodighiero; Guiotto; Pastorini, Farmaco, Edizione Scientifica, 1981, vol. 36, # 7, p. 648 - 662

  摘要：

  DOI：
• 作为产物：
  描述：

  7-allyloxy-8-iodo-4-methyl-2H-1-benzopyran-2-one 在 N,N-二甲基苯胺 作用下， 反应 6.0h， 以76%的产率得到6-allyl-7-hydroxy-4-methyl-2H-1-benzopyran-2-one
  参考文献：
  名称：

  A convenient synthesis of psoralen derivatives: Psoralen, 4-methyl-psoralen and 4-phenyl-psoralen

  摘要：

  DOI：

  10.1007/bf00899252

文献信息

• Establishing a Flow Process to Coumarin-8-Carbaldehydes as Important Synthetic Scaffolds
  作者：Jaroslav Zak、David Ron、Elena Riva、Heather P. Harding、Benedict C. S. Cross、Ian R. Baxendale

  DOI：10.1002/chem.201201039

  日期：2012.8.6

  Despite their usefulness as fluorophores and synthetic precursors, efficient and reliable routes to coumarin‐8‐carbaldehydes are lacking. We describe here a high‐yielding continuous flow synthesis that requires no manual intermediate purification or work‐up, giving access to multigram quantities of the aldehyde product.

  尽管它们可用作荧光团和合成前体，但仍缺乏高效，可靠的香豆素-8甲醛合成途径。我们在这里描述了一种高产量的连续流合成方法，不需要人工进行中间纯化或后处理，可以得到数克量的醛产品。
• An efficient regioselective bromination protocol of activated coumarins using 2,4,4,6-tetrabromo-2,5-cyclohexadienone
  作者：Nemai C. Ganguly、Subhasis Nayek、Sumanta Chandra

  DOI：10.1139/cjc-2013-0230

  日期：2013.11

  2,4,4,6-Tetrabromo-2,5-cyclohexadienone mediated bromination of a wide assortment of activated coumarins in acetonitrile has been accomplished with high regioselectivity and good to excellent yields. The selectivity and efficiency of bromination were found to be markedly dependent on electronic factors, particularly degree of electron withdrawal from electron-releasing 7-oxygenated substituents to the C-3 position of the α-pyrone moiety by vinylogous resonance and the presence of nucleophilic additives such as water and tetra-n-butylammonium bromide in the reaction medium. The sole by-product of the reaction was converted back to the reagent by oxidation with KBr−KBrO₃, which was recycled three times without significant loss of efficiency.

  在乙腈中，2,4,4,6-四溴-2,5-环己二酮介导的对活化香豆素的溴化反应以高区域选择性和良好至优良的产率完成。发现溴化的选择性和效率在很大程度上取决于电子因素，特别是从电子给予的7-氧代取代基到α-吡喃酮部分的C-3位置的电子撤离程度，通过共轭共振和在反应介质中存在水和四正丁基溴化铵等亲核添加剂。反应的唯一副产物通过氧化与KBr−KBrO₃转化回试剂，试剂可以循环使用三次而不会显著损失效率。
• Synthesis and anti-proliferative activity of novel oxepin-annulated coumarins
  作者：Saisuree Prateeptongkum、Wiratchanee Mahavorasirikul、Nongnaphat Duangdee

  DOI：10.24820/ark.5550190.p010.547

  日期：——

  A series of fused dihydrooxepino[h]and dihydrooxepino[g]coumarins (7 and 8) were synthesized through allylation, Claisen rearrangement, allylation and ring-closing metathesis (RCM), respectively. All the synthesized compounds were characterized by appropriate spectral analysis. The anti-proliferative activities of compound 5a-c, 6a, 6c, 7a-c and 8a-c were evaluated against human colon cancer (Caco-2)

  分别通过烯丙基化、克莱森重排、烯丙基化和闭环复分解 (RCM) 合成了一系列稠合的二氢氧杂[h] 和二氢氧杂[g] 香豆素（7 和 8）。通过适当的光谱分析表征所有合成的化合物。使用以下方法评估了化合物 5a-c、6a、6c、7a-c 和 8a-c 对人结肠癌 (Caco-2)、肝癌 (HepG2) 和乳腺癌 (SKBR-3) 细胞系的抗增殖活性他莫昔芬 (TAM) 作为阳性对照。与所有其他香豆素衍生物相比，化合物 7b 对抗性 Caco-2 和 SKBR-3 细胞系显示出显着的抗增殖活性。有趣的是，化合物 8b 比 TAM 更有效地对抗敏感的 HepG2 细胞系。
• AHULWALIA V. K.; PRAKASH C.; BALA S., MONATSH. CHEM., 1980, 111, NO 4, 877-882
  作者：AHULWALIA V. K.、 PRAKASH C.、 BALA S.

  DOI：——

  日期：——
• USE OF NATURAL PRODUCTS AND RELATED SYNTHETIC COMPOUNDS FOR THE TREATMENT OF CARDIOVASCULAR DISEASE
  申请人：THE UNIVERSITY OF SYDNEY

  公开号：EP0703780A1

  公开（公告）日：1996-04-03