(8R,9S,13S,14S)-3-[ditert-butyl(hydroxy)silyl]oxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one | 1315577-32-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (8R,9S,13S,14S)-3-[ditert-butyl(hydroxy)silyl]oxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
• CAS: 1315577-32-2
• 化学式: C₂₆H₄₀O₃Si
• 分子量: 428.687
• InChiKey: VGSBOOVMGFICLM-CQAGSAPUSA-N

物化性质

• 沸点：
  515.1±60.0 °C(Predicted)
• 密度：
  1.054±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.53
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (8R,9S,13S,14S)-3-[ditert-butyl(hydroxy)silyl]oxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one 在 Pd(opiv)2 、 碘苯二乙酸 、 四丁基氟化铵 、 水 作用下， 以 甲苯 、 四氢呋喃 为溶剂， 以88%的产率得到2-羟基雌酚酮
  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：

  di-tert-butylchlorosilane 在 咪唑 、 N-溴代丁二酰亚胺(NBS) 、 水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (8R,9S,13S,14S)-3-[ditert-butyl(hydroxy)silyl]oxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
  参考文献：
  名称：

  Silanol: A Traceless Directing Group for Pd-Catalyzed o-Alkenylation of Phenols

  摘要：

  A silanol-directed, Pd(II)-catalyzed C-H alkenylation of phenols is reported. This work features silanol, as a novel traceless directing group, and a directed o-C-H alkenylation of phenols. This new method allows for efficient synthesis of diverse alkenylated phenols, including an estrone derivative.

  DOI：

  10.1021/ja204924j

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。
• Silanol: A Traceless Directing Group for Pd-Catalyzed <i>o</i>-Alkenylation of Phenols
  作者：Chunhui Huang、Buddhadeb Chattopadhyay、Vladimir Gevorgyan

  DOI：10.1021/ja204924j

  日期：2011.8.17

  A silanol-directed, Pd(II)-catalyzed C-H alkenylation of phenols is reported. This work features silanol, as a novel traceless directing group, and a directed o-C-H alkenylation of phenols. This new method allows for efficient synthesis of diverse alkenylated phenols, including an estrone derivative.
• 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: