naphthalene-1,7-diyl bis(trifluoromethanesulfonate) | 152873-81-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: naphthalene-1,7-diyl bis(trifluoromethanesulfonate)
• 英文别名: [8-(Trifluoromethylsulfonyloxy)naphthalen-2-yl] trifluoromethanesulfonate
• CAS: 152873-81-9
• 化学式: C₁₂H₆F₆O₆S₂
• 分子量: 424.298
• InChiKey: YNJXULJDEQOJFG-UHFFFAOYSA-N

物化性质

• 沸点：
  444.6±45.0 °C(Predicted)
• 密度：
  1.721±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  naphthalene-1,7-diyl bis(trifluoromethanesulfonate) 在 bis-triphenylphosphine-palladium(II) chloride 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride sodium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 13.0h， 生成 dimethyl 2,2'-[naphthalene-1,7-diylbis(3-methoxy-5-oxofuran-4-yl-2-ylidene)]bis[(4-benzyloxyphenyl)acetate]
  参考文献：
  名称：

  通过苄基化中间体的 Suzuki-Miyaura 交叉偶联合成 Pulvinic Acid 和 Norbadione A 类似物

  摘要：

  可以通过官能化芳基硼酸酯与适当的乙烯基三氟甲磺酸酯的 Suzuki-Miyaura 交叉偶联制备叶绿酸和降冰片二酮 A 类似物，其中羟基官能团用甲基或苄基保护，后者在合成序列结束。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

  DOI：

  10.1002/ejoc.200500837
• 作为产物：
  描述：

  三氟甲磺酸酐 、 1,7-二羟基萘 在 吡啶 作用下， 以95%的产率得到naphthalene-1,7-diyl bis(trifluoromethanesulfonate)
  参考文献：
  名称：

  通过苄基化中间体的 Suzuki-Miyaura 交叉偶联合成 Pulvinic Acid 和 Norbadione A 类似物

  摘要：

  可以通过官能化芳基硼酸酯与适当的乙烯基三氟甲磺酸酯的 Suzuki-Miyaura 交叉偶联制备叶绿酸和降冰片二酮 A 类似物，其中羟基官能团用甲基或苄基保护，后者在合成序列结束。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

  DOI：

  10.1002/ejoc.200500837

文献信息

• 3-Aryltetronic Acids: Efficient Preparation and Use as Precursors for Vulpinic Acids
  作者：Aurélie Mallinger、Thierry Le Gall、Charles Mioskowski

  DOI：10.1021/jo802038z

  日期：2009.2.6

  3-Aryltetronic acids were prepared in one step by treatment of a mixture of methyl arylacetates and methyl hydroxyacetates with potassium tert-butoxide, via tandem transesterification/Dieckmann condensation. Several mushroom or lichen pigments, vulpinic acids, were synthesized from 3-(4-methoxyphenyl)tetronic acid in three steps involving the reaction of the corresponding dianion with an α-ketoester

  通过串联酯交换反应/ Dieckmann缩合反应，用叔丁醇钾处理芳基乙酸甲酯和羟基乙酸甲酯的混合物，一步制得3-芳基酸。在三个步骤中，由3-（4-甲氧基苯基）tetronic酸合成了几种蘑菇或地衣颜料的硫化松香酸，这三个步骤涉及相应的二价阴离子与α-酮酸酯的反应以及所获得的叔醇的脱水成（E）的混合物-和（Z）-烯烃，它们在254nm的紫外线辐射下转化为天然（E）-异构体。樟脑酸，4,4'-二甲氧基硫代乙酸的合成，以及最近分离出的甲基3'，5'-dichloro-4,4'-di- O的首次合成因此，以有效的方式获得了苹果酸-草酸甲酯。
• Brønsted Acid-catalyzed Tandem Cycloaromatization of Naphthalene-based Bisacetals: Selective Synthesis of <i>ortho</i>-Fused Six-hexagon Benzenoids
  作者：Ikko Takahashi、Masaki Hayashi、Takeshi Fujita、Junji Ichikawa

  DOI：10.1246/cl.161122

  日期：2017.3.5

  amount of trifluoromethanesulfonic acid in 1,1,1,3,3,3-hexafluoropropan-2-ol. Five substrates were successfully employed in this protocol to afford ortho-fused six-hexagon benzenoids with high selectivities and in excellent yields.

  带有两个由亚甲基-2,1-亚苯基连接的缩醛部分的萘使用催化量的三氟甲磺酸在 1,1,1,3,3,3-六氟丙-2-醇中进行区域选择性串联环芳构化。在该协议中成功使用了五种底物，以提供具有高选择性和优异产量的邻位融合六六边形苯类。
• Lactone compounds which can be used as antioxidant agents in pharmaceutical, cosmetic or food compositions and their method of preparation
  申请人：Mioskoski Charles

  公开号：US20110098351A1

  公开（公告）日：2011-04-28

  The subject of the present invention is specific lactone compounds which can be used as antioxidant agents in pharmaceutical or cosmetic compositions or in food products, the said compounds containing a naphthalene ring onto which two lactone units are grafte.

  本发明涉及特定的内酯化合物，可用作药用或化妆品组合物或食品产品中的抗氧化剂，所述化合物含有一个萘环，上面嫁接了两个内酯单元。
• Norbadione A: Synthetic Approach to the Bis(pulvinic acid) Moiety and Cesium-Complexation Studies
  作者：Marine Desage-El Murr、Stéphanie Nowaczyk、Thierry Le Gall、Charles Mioskowski、Badia Amekraz、Christophe Moulin

  DOI：10.1002/anie.200390332

  日期：2003.3.17
• [2.2]Naphthalenophanes from intermolecular [2 + 2] photocycloadditions of divinylnaphthalenes
  作者：Motoharu Takeuchi、Takeshi Tuihiji、J. Nishimura

  DOI：10.1021/jo00078a016

  日期：1993.12

  syn-[2.2]Naphthalenophanes were obtained exclusively in reasonable yields from the intermolecular [2 + 2] photocycloadditions of divinylnaphthalenes. The position of the vinyl group and the type of vinyl substituent affected the isomer ratio of the products. The structures of naphthalenophanes were elucidated by H-1-NMR spectroscopy including COSY and NOESY experiments. Among the divinylnaphthalenes examined, 1,4-, 1,5-, and 1,6-ones did not give the desired naphthalenophanes. By taking advantage of the effect of the substituents on the photoreaction, we could obtain [2.2]-(1,5)naphthalenophane derivatives from 1,5-bis(beta-carbethoxyethenyl)naphthalene and 1,5-bis(beta-phenylethenyl)naphthalene, but we could not obtain the 1,4-isomers, probably because they are highly strained. Although a mixture of two different divinylnaphthalenes was irradiated, only homo-adducts were obtained; no cross adducts were detected.