2-(methylthio)-3-(thiophen-2-yl)benzofuran | 1128143-84-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 2-(methylthio)-3-(thiophen-2-yl)benzofuran
• 英文别名: 2-Methylsulfanyl-3-thiophen-2-yl-1-benzofuran
• CAS: 1128143-84-9
• 化学式: C₁₃H₁₀OS₂
• 分子量: 246.354
• InChiKey: WNHBGNTZJYZGHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  66.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-iodo-2-(methylsulfanyl)benzo[b]furan 、 chlorozinc(1+),2H-thiophen-2-ide 在 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以61%的产率得到2-(methylthio)-3-(thiophen-2-yl)benzofuran
  参考文献：
  名称：

  Electrophilic Cyclization of 2-Chalcogenealkynylanisoles: Versatile Access to 2-Chalcogen-benzo[b]furans

  摘要：

  An efficient synthesis of 2-chalcogen-3-substituted-benzo[b]furan compounds has been accomplished via electrophilic cyclization reaction of 2-chalcogenealkynyl anisoles using I-2, ICl, Br-2 and PhSeBr as electrophile sources. The product distributions were strongly dependent on the nature of substituents in the aromatic ring of anisole and on the chalcogen atom directly bonded to the triple bond. The 2-chalcogen-3-iodo-benzo[b]furans obtained smoothly underwent conversion to more complex structures of benzo[b]furan derivatives via palladium- or copper-catalyzed cross-coupling reaction with thiols, diphenyl diselenides, and zincates.

  DOI：

  10.1021/jo802736e

文献信息

• Palladium catalyzed Suzuki cross-coupling of 3-iodo-2-(methylthio)-benzo[b]furan derivatives: synthesis of 3-aryl-2-(methylthio)benzo[b]furans
  作者：Rafaela M Gay、Flávia Manarin、Ricardo Brandão、Gilson Zeni

  DOI：10.1590/s0103-50532010000900006

  日期：——

  A selective and efficient method for the synthesis of 3-aryl-2-(methylthio)benzo[ b]furans derivatives by palladium catalyzed cross-coupling reaction with boronic acids has been developed. The reaction proceeded cleanly under mild conditions and was performed with aryl boronic acids bearing electron-withdrawing, electron donating and neutral substituents.

  开发了一种选择性和有效的方法，该方法通过钯与硼酸的交叉偶联反应合成3-芳基-2-（甲硫基）苯并[b]呋喃衍生物。反应在温和条件下干净地进行，并用带有吸电子，给电子和中性取代基的芳基硼酸进行。
• Electrophilic Cyclization of 2-Chalcogenealkynylanisoles: Versatile Access to 2-Chalcogen-benzo[<i>b</i>]furans
  作者：Flávia Manarin、Juliano A. Roehrs、Rafaela Mozzaquatro Gay、Ricardo Brandão、Paulo H. Menezes、Cristina W. Nogueira、Gilson Zeni

  DOI：10.1021/jo802736e

  日期：2009.3.6

  An efficient synthesis of 2-chalcogen-3-substituted-benzo[b]furan compounds has been accomplished via electrophilic cyclization reaction of 2-chalcogenealkynyl anisoles using I-2, ICl, Br-2 and PhSeBr as electrophile sources. The product distributions were strongly dependent on the nature of substituents in the aromatic ring of anisole and on the chalcogen atom directly bonded to the triple bond. The 2-chalcogen-3-iodo-benzo[b]furans obtained smoothly underwent conversion to more complex structures of benzo[b]furan derivatives via palladium- or copper-catalyzed cross-coupling reaction with thiols, diphenyl diselenides, and zincates.