2,2-di-tert-butylbenzo[d][1,3,2]dioxasilole | 1344113-53-6

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 2,2-di-tert-butylbenzo[d][1,3,2]dioxasilole
• 英文别名: 2,2-Ditert-butyl-1,3,2-benzodioxasilole；2,2-ditert-butyl-1,3,2-benzodioxasilole
• CAS: 1344113-53-6
• 化学式: C₁₄H₂₂O₂Si
• 分子量: 250.413
• InChiKey: ZQINQXWLSJCEDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2-di-tert-butylbenzo[d][1,3,2]dioxasilole 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到邻苯二酚
  参考文献：
  名称：

  Synthesis of Catechols from Phenols via Pd-Catalyzed Silanol-Directed C–H Oxygenation

  摘要：

  A silanol-directed, Pd-catalyzed C-H oxygenation of phenols into catechols is presented. This method is highly site selective and general, as it allows for oxygenation of not only electron-neutral but also electron-poor phenols. This method operates via a silanol-directed acetoxylation, followed by a subsequent acid-catalyzed cyclization reaction into a cyclic silicon protected catechol, A routine desilylation of the silacyle With TBAF uncovers the catechol product:

  DOI：

  10.1021/ja208572v
• 作为产物：
  描述：

  苯酚 在 咪唑 、 bis(η3-allyl-μ-chloropalladium(II)) 、 碘苯二乙酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 16.0h， 生成 2,2-di-tert-butylbenzo[d][1,3,2]dioxasilole
  参考文献：
  名称：

  Synthesis of Catechols from Phenols via Pd-Catalyzed Silanol-Directed C–H Oxygenation

  摘要：

  A silanol-directed, Pd-catalyzed C-H oxygenation of phenols into catechols is presented. This method is highly site selective and general, as it allows for oxygenation of not only electron-neutral but also electron-poor phenols. This method operates via a silanol-directed acetoxylation, followed by a subsequent acid-catalyzed cyclization reaction into a cyclic silicon protected catechol, A routine desilylation of the silacyle With TBAF uncovers the catechol product:

  DOI：

  10.1021/ja208572v

文献信息

• Synthesis of Catechols from Phenols via Pd-Catalyzed Silanol-Directed C–H Oxygenation
  作者：Chunhui Huang、Nugzar Ghavtadze、Buddhadeb Chattopadhyay、Vladimir Gevorgyan

  DOI：10.1021/ja208572v

  日期：2011.11.9

  A silanol-directed, Pd-catalyzed C-H oxygenation of phenols into catechols is presented. This method is highly site selective and general, as it allows for oxygenation of not only electron-neutral but also electron-poor phenols. This method operates via a silanol-directed acetoxylation, followed by a subsequent acid-catalyzed cyclization reaction into a cyclic silicon protected catechol, A routine desilylation of the silacyle With TBAF uncovers the catechol product: