Ditert-butyl-hydroxy-naphthalen-2-yloxysilane | 1344113-51-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Ditert-butyl-hydroxy-naphthalen-2-yloxysilane
• CAS: 1344113-51-4
• 化学式: C₁₈H₂₆O₂Si
• 分子量: 302.489
• InChiKey: YSNMKQXAJNEJLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.25
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Ditert-butyl-hydroxy-naphthalen-2-yloxysilane 在 Pd(opiv)2 、 碘苯二乙酸 、 四丁基氟化铵 、 水 作用下， 以 三氟甲苯 、 四氢呋喃 为溶剂， 生成 2,3-二羟基萘
  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：

  二叔丁基硅烷 在 咪唑 、 溴 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 Ditert-butyl-hydroxy-naphthalen-2-yloxysilane
  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

• General Method for the Synthesis of Salicylic Acids from Phenols through Palladium-Catalyzed Silanol-Directed CH Carboxylation
  作者：Yang Wang、Vladimir Gevorgyan

  DOI：10.1002/anie.201410375

  日期：2015.2.9

  silanol‐directed, palladium‐catalyzed CH carboxylation reaction of phenols to give salicylic acids has been developed. This method features high efficiency and selectivity, and excellent functional‐group tolerance. The generality of this method was demonstrated by the carboxylation of estrone and by the synthesis of an unsymmetrically o,o′‐disubstituted phenolic compound through two sequential CH functionalization

  已经开发出一种硅烷醇引导、钯催化的苯酚 C → H 羧化反应，生成水杨酸。该方法具有高效、选择性高、官能团耐受性好的特点。该方法的通用性通过雌酮的羧化和通过两个连续的C - H官能化过程合成不对称o , o'-二取代酚类化合物得到证明。