2-(5-bromobenzo[d-1,3]dioxol-6-yl)-3-(2-furanyl)-3-(methylthio)-2-propenenitrile | 1012327-23-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 2-(5-bromobenzo[d-1,3]dioxol-6-yl)-3-(2-furanyl)-3-(methylthio)-2-propenenitrile
• 英文别名: 2-(5-bromobenzo[d][1,3]dioxol-6-yl)-3-(methylthio)-3-(furan-2-yl)acrylonitrile
• CAS: 1012327-23-9
• 化学式: C₁₅H₁₀BrNO₃S
• 分子量: 364.219
• InChiKey: NBCFTCXMFHQOKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.53
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  55.39
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-(5-bromobenzo[d-1,3]dioxol-6-yl)-3-(2-furanyl)-3-(methylthio)-2-propenenitrile 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以53%的产率得到6-(2-(furan-2-yl)ethynyl)benzo[d][1,3]dioxole-5-carbonitrile
  参考文献：
  名称：

  A Novel Anionic Domino Process for the Synthesis of o-Cyanoaryl-Methylthio/Alkyl/Aryl/Heteroaryl Acetylenes

  摘要：

  A novel unexpected anionic domino process involving n-BuLi-induced rearrangement of 3,3-bis(methylthio) or 3-methylthio-3-aryl/heteroaryl/alkyl-o-bromoarylacrylonitriles to o-cyanoarylacetylenes in synthetically useful yields has been reported. The scope and generality of the reaction has been examined, and a possible mechanism has been proposed.

  DOI：

  10.1021/ol800029c
• 作为产物：
  描述：

  2-Furandithiocarbonsaeure-methylester 、 2-(6-溴苯并[1,3]二氧杂环戊烯-5-基)乙腈 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 以90%的产率得到2-(5-bromobenzo[d-1,3]dioxol-6-yl)-3-(2-furanyl)-3-(methylthio)-2-propenenitrile
  参考文献：
  名称：

  A Novel Anionic Domino Process for the Synthesis of o-Cyanoaryl-Methylthio/Alkyl/Aryl/Heteroaryl Acetylenes

  摘要：

  A novel unexpected anionic domino process involving n-BuLi-induced rearrangement of 3,3-bis(methylthio) or 3-methylthio-3-aryl/heteroaryl/alkyl-o-bromoarylacrylonitriles to o-cyanoarylacetylenes in synthetically useful yields has been reported. The scope and generality of the reaction has been examined, and a possible mechanism has been proposed.

  DOI：

  10.1021/ol800029c

文献信息

• Synthesis of Novel Substituted Phenanthrenes and Polycyclic Heteroarenes by Pd-Catalyzed, Direct, Intramolecular Arylation/Heteroarylation
  作者：Ashok K. Yadav、Hiriyakkanavar Ila、Hiriyakkanavar Junjappa

  DOI：10.1002/ejoc.200901036

  日期：2010.1

  A novel route to substituted phenanthrenes and polycyclic heteroarenes by direct, Pd-catalyzed, intramolecular arylation/heteroarylation of 2-(2-bromoaryl/heteroaryl)-3-(aryl/heteroaryl)-3-(methylthio)acrylonitriles has been reported.

  已经报道了通过 2-(2-溴芳基/杂芳基)-3-(芳基/杂芳基)-3-(甲硫基)丙烯腈的直接、Pd 催化、分子内芳基化/杂芳基化制备取代菲和多环杂芳烃的新途径。