甲磺酸,三氟-,2H-1-苯并吡喃-3-基酯 | 194665-78-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 甲磺酸,三氟-,2H-1-苯并吡喃-3-基酯
• 英文名称: 2H-chromen-3-yl trifluoromethanesulfonate
• 英文别名: Trifluoromethanesulfonic acid 2H-1-benzopyran-3-yl ester
• CAS: 194665-78-6
• 化学式: C₁₀H₇F₃O₄S
• 分子量: 280.224
• InChiKey: FMWSAHMJAFQVDS-UHFFFAOYSA-N

物化性质

• 沸点：
  346.4±42.0 °C(Predicted)
• 密度：
  1.57±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  甲磺酸,三氟-,2H-1-苯并吡喃-3-基酯 在 bis-triphenylphosphine-palladium(II) chloride 、 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 六甲基磷酰三胺 、 二氯甲烷 为溶剂， 反应 21.0h， 生成 3-methylchroman
  参考文献：
  名称：

  A new route to 3,4-dihydro-2H-1-benzopyrans substituted at 3-position via palladium-catalysed reactions

  摘要：

  3,4-Dihydro-2H-1-benzopyrans substituted at 3-position were prepared via palladium-catalysed reactions between a triflate and several coupling reagents (alkyl or aryl tin reagents and borane derivatives) according to Stille or Suzuki methodologies. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01209-4
• 作为产物：
  描述：

  2H-苯并吡喃-3-甲酸 在 叠氮磷酸二苯酯 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 二氯甲烷 、 三乙胺 、 甲苯 为溶剂， 反应 10.42h， 生成 甲磺酸,三氟-,2H-1-苯并吡喃-3-基酯
  参考文献：
  名称：

  通过功能性吡啶基锌试剂和钯催化的交叉偶联反应有效合成新的杂类胡萝卜素

  摘要：

  描述了由 6-溴-2-吡啶基氯化锌 (11) 聚合合成带有色烯环和吡啶基或乙炔基吡啶基部分的杂芳烃类化合物 4、5a 和 5b。这种新的功能杂芳基锌试剂很容易从 2,6-二溴吡啶中获得，可以进行选择性钯催化的碳-碳键形成反应，以产生相应的 6-取代-2-溴吡啶 13。 13得到锌衍生物14，随后在钯催化条件下与4-碘苯甲酸乙酯偶联得到杂芳烃4。取代的溴吡啶13或三氟甲磺酸酯22与适当的炔烃在Sonogashira条件下偶联得到相应的杂芳烃5a、5b和6 .

  DOI：

  10.1002/1099-0690(200111)2001:22<4207::aid-ejoc4207>3.0.co;2-3

文献信息

• Hydrovinylation of 1,3-Dienes:  A New Protocol, an Asymmetric Variation, and a Potential Solution to the Exocyclic Side Chain Stereochemistry Problem
  作者：Aibin Zhang、T. V. RajanBabu

  DOI：10.1021/ja0561338

  日期：2006.1.1

  Cyclic and acyclic 1,3-dienes undergo efficient (substrate/catalyst = 72) heterodimerization with ethylene in the presence of a Ni catalyst prepared from [o-(PhCH2O)]C6H4PPh2, [(allyl)2NiBr]2, and Na+ BAr4- (Ar = 3,5-bis-trifluromethylphenyl), giving 1,2-addition products. Yields up to 99% can be realized for several 1-vinylcycloalkenes and 1-substituted 1,3-butadienes. Phospholanes with suitably placed hemilabile ligating groups and phosphoramidites derived from binaphthol are excellent ligands for an asymmetric variation of this reaction, the latter giving 99% yield and >95% ee's for selected substrates. An example of how an exocyclic chiral center can be used to install other stereo-centers in the ring (e. g., the carbon to which the side chain is attached) is also provided. These discoveries open an expeditious entry into several biologically relevant classes of compounds, especially those carrying tetrahydronaphthalene and related heterocyclic moieties.
• Efficient Syntheses of New Heteroarotinoids through Functional Pyridylzinc Reagents and Palladium-Catalyzed Cross-Coupling Reactions
  作者：Mouâd Alami、Jean-François Peyrat、Larbi Belachmi、Jean-Daniel Brion

  DOI：10.1002/1099-0690(200111)2001:22<4207::aid-ejoc4207>3.0.co;2-3

  日期：2001.11

  rings in association with pyridyl or ethynylpyridyl moieties, from 6-bromo-2-pyridylzinc chloride (11) is described. This new functional heteroarylzinc reagent, readily accessible from 2,6-dibromopyridine, may undergo a selective palladium-catalyzed carbon−carbon bond-forming reaction to yield the corresponding 6-substituted-2-bromopyridines 13. Further manipulation of the remaining bromine atom in 13

  描述了由 6-溴-2-吡啶基氯化锌 (11) 聚合合成带有色烯环和吡啶基或乙炔基吡啶基部分的杂芳烃类化合物 4、5a 和 5b。这种新的功能杂芳基锌试剂很容易从 2,6-二溴吡啶中获得，可以进行选择性钯催化的碳-碳键形成反应，以产生相应的 6-取代-2-溴吡啶 13。 13得到锌衍生物14，随后在钯催化条件下与4-碘苯甲酸乙酯偶联得到杂芳烃4。取代的溴吡啶13或三氟甲磺酸酯22与适当的炔烃在Sonogashira条件下偶联得到相应的杂芳烃5a、5b和6 .
• A new route to 3,4-dihydro-2H-1-benzopyrans substituted at 3-position via palladium-catalysed reactions
  作者：Stéphanie Usse、Gérald Guillaumet、Marie-Claude Viaud

  DOI：10.1016/s0040-4039(97)01209-4

  日期：1997.8

  3,4-Dihydro-2H-1-benzopyrans substituted at 3-position were prepared via palladium-catalysed reactions between a triflate and several coupling reagents (alkyl or aryl tin reagents and borane derivatives) according to Stille or Suzuki methodologies. (C) 1997 Published by Elsevier Science Ltd.