2-isopropyl-3-(trifluoromethanesulfonyloxy)psoralen | 1332511-78-0

• 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: 2-isopropyl-3-(trifluoromethanesulfonyloxy)psoralen
• 英文别名: 2-Isopropyl-7-oxo-7h-furo[3,2-g]chromen-3-yl trifluoromethanesulfonate；(7-oxo-2-propan-2-ylfuro[3,2-g]chromen-3-yl) trifluoromethanesulfonate
• CAS: 1332511-78-0
• 化学式: C₁₅H₁₁F₃O₆S
• 分子量: 376.31
• InChiKey: VUPIDFYSDSQKFK-UHFFFAOYSA-N

物化性质

• 熔点：
  181-182 °C(Solvent: Diethyl ether)
• 沸点：
  476.4±45.0 °C(Predicted)
• 密度：
  1.532±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  91.2
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-isopropyl-3-(trifluoromethanesulfonyloxy)psoralen 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 copper(I) bromide 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 10.0h， 生成 3-[1-(4-hydroxy-2,3,5,6-tetramethylbenzyl)-1H-1,2,3-triazol-4-yl]-2-isopropyl-7H-furo[3,2-g]chromen-7-one
  参考文献：
  名称：

  Plant coumarins: XV. Oreoselone in the synthesis of 3-[(Z)-alkenyl]- and 3-(1H-1,2,3-triazol-4-yl)psoralens

  摘要：

  Sonogashira reaction of 2-isopropyl-3-(trifluoromethanesulfonyloxy)psoralen with terminal arylacetylenes gave 2-isopropyl-3-(arylethynyl)psoralens which were converted into the corresponding Z-alkenes by reduction with hydrogen in the presence of Lindlar catalyst or by thermal decomposition of preliminarily prepared Ti(II)-alkyne complexes. The reaction of 2-isopropyl-3-(trifluoromethanesulfonyloxy)psoralen with trimethylsilylacetylene afforded 2-isopropyl-3-[(trimethylsilyl)ethynyl]psoralen which reacted with 4-(omega-azidoalkyl) phenols in the presence of copper(I) bromide and triethylamine to produce 3-{1-[omega-(4-hydroxyaryl)-alkyl]-1H-1,2,3-triazol-4-yl}-2-isopropylpsoralens.

  DOI：

  10.1134/s1070428015070012x
• 作为产物：
  描述：

  三氟甲磺酸酐 、 2-(1-methylethylidene)-7H-furo[3,2-g][1]benzopyran-3,7-dione 在 吡啶 作用下， 反应 12.5h， 以72%的产率得到2-isopropyl-3-(trifluoromethanesulfonyloxy)psoralen
  参考文献：
  名称：

  Plant coumarins: VI. Synthesis of 3-vinylfurocoumarin derivatives based on oreoselone

  摘要：

  Palladium-catalyzed Heck reaction of oreoselone trifluoromethanesulfonate with various terminal alkenes (methyl acrylate, styrene, vinylpyridines, N-vinylpyrrole, and N-vinyl-1,2,4-triazole) led to the formation of the corresponding (E)-3-vinyl-7H-furo[3,2-g]chromen-7-ones. The yield was found to depend on the catalytic system and initial olefin structure.

  DOI：

  10.1134/s1070428011070190

文献信息

• Plant coumarins: VII. Amination of oreoselone trifluoromethanesulfonate
  作者：A. V. Lipeeva、E. E. Shul’ts、M. M. Shakirov、G. A. Tolstikov

  DOI：10.1134/s1070428011090235

  日期：2011.9

  Amination of oreoselone trifluoromethanesulfonate with N-substituted piperazines, anabasine, aniline derivatives, quinolin- and isoquinolinamines, and amino acids of the penicillin and cephalosporin series in the presence of palladium complexes gave the corresponding N-substituted 3-aminofurocoumarins. The yield of the amination products depended on the catalytic system and base used.

  在钯配合物的存在下，用N-取代的哌嗪，鸟嘌呤，苯胺衍生物，喹啉和异喹啉胺以及青霉素和头孢菌素系列的氨基酸胺化三氟甲磺酸甲醚，得到相应的N-取代的3-氨基呋喃香豆素。胺化产物的产率取决于所使用的催化体系和碱。
• Synthesis and Cytotoxic Activity of a New Group of Heterocyclic Analogues of the Combretastatins
  作者：Alla Lipeeva、Elvira Shults、Makhmut Shakirov、Mikhail Pokrovsky、Andrey Pokrovsky

  DOI：10.3390/molecules19067881

  日期：——

  A series of new analogs of combretastatin A-4 (CA-4, 1) with the A or B-ring replaced by a 3-oxo-2,3-dihydrofurocoumarin or a furocoumarin residue have been designed and synthesized by employing a cross-coupling approach. All the compounds were evaluated for their cytotoxic activity with respect to model cancer cell lines (CEM-13, MT-4, U-937) using conventional MTT assays. Structure-activity relationship

  一系列新的考布他汀 A-4 类似物 (CA-4, 1) 的 A 或 B 环被 3-氧代-2,3-二氢呋喃香豆素或呋喃香豆素残基取代，已通过使用交叉设计和合成。耦合方法。使用常规 MTT 测定法评估所有化合物对模型癌细胞系（CEM-13、MT-4、U-937）的细胞毒活性。构效关系分析表明，其中 (Z)-苯乙烯基取代基连接到 3-oxo-2,3-dihydrofurocoumarin 核心的 2-位的化合物 2, 3, 6-8 与 3 -(Z)-苯乙烯基呋喃香豆素 4、5、9-11。(Z)-苯乙烯基部分的芳环上的甲氧基、羟基和甲酰基取代似乎在此类化合物中起重要作用。化合物 2 和 3 对 CEM-13 细胞系显示出最佳效力，CTD50 值范围为 4.9 至 5.1 μM。与 CA-4 相比，所有合成的化合物对 T 细胞人类白血病细胞 MT-4 和淋巴母细胞白血病细胞 CEM-13 都表现出中
• Synthesis, in vivo Anticoagulant Evaluation and Molecular Docking Studies of Bicoumarins Obtained from Furocoumarin Peucedanin
  作者：Alla V. Lipeeva、Mikhail V. Khvostov、Dmitry S. Baev、Makhmut M. Shakirov、Tatijana G. Tolstikova、Elvira E. Shults

  DOI：10.2174/1573406412666160129105115

  日期：2016.9.27

  3-dihydrofurocoumarin and furocoumarin-2,3-dihydrofurocoumarin hybrids was performed by two alternative pathways, either involving a catalyzed transformations of the ethynyl derivatives of plant coumarins - peucedanin or peuruthenicin. OBJECTIVE AND METHODS The Sonogashira reaction of 7-ethynyl coumarins or 3-ethynyl-2-isopropylpsoralen with the subsequent coumarin triflates led to 7,7´-linked bicoumarins or 3

  背景技术7，7。连接的双香豆素，3，3。连接的双（2-异丙基）补骨脂素以及1H-1,2,3-三唑连接的香豆素-2,3-二氢呋喃香豆素和呋喃香豆素-2,3的合成-二氢呋喃香豆素杂种通过两种替代途径进行，涉及植物香豆素的乙炔基衍生物-Peucedanin或peuruthenicin的催化转化。目的和方法7-乙炔基香豆素或3-乙炔基-2-异丙基补骨脂素与随后的香豆素三氟甲磺酸酯的Sonogashira反应导致7,7′-连接的双香豆素或3,3′-连接的双补骨脂素。1,2,3-三唑连接的香豆素-2,3-二氢呋喃香豆素或呋喃香豆素-2,3-二氢呋喃香豆素杂化物是通过2-氮杂环戊酮与7-炔基香豆素或3-乙炔基-2-异丙基补骨脂素的区域选择性Cu催化的环加成反应合成的。结果合成的双香豆素在体内具有抗凝活性的药理学筛选显示，与1,2,3-三唑环20和22连接的香豆素-二氢呋喃香豆素杂种是活性最高的化合物。所呈递的凝血酶原时间（PT）值与100
• Plant coumarins: VIII. Suzuki reaction in the synthesis of 3-aryl(hetaryl)furocoumarins
  作者：A. V. Lipeeva、E. E. Shul’ts、M. M. Shakirov、G. A. Tolstikov

  DOI：10.1134/s1070428011090247

  日期：2011.9

  Suzuki cross coupling of oreoselone trifluoromethanesulfonate with substituted phenyl- and hetarylboronic acids in the presence of palladium complexes with uni- and bidentate ligands gave the corresponding 3-substituted furocoumarins.