[(8R,9S,10R,13S,14S)-10,13-dimethyl-3-trimethylsilyloxy-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-17-yl]oxy-trimethylsilane | 32206-51-2

• 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,10R,13S,14S)-10,13-dimethyl-3-trimethylsilyloxy-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-17-yl]oxy-trimethylsilane
• CAS: 32206-51-2；147729-21-3
• 化学式: C₂₅H₄₄O₂Si₂
• 分子量: 432.794
• InChiKey: VEYGGCOAFMQLPU-ZUNILWNPSA-N

物化性质

• 沸点：
  438.4±45.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.51
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 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：

  [(8R,9S,10R,13S,14S)-10,13-dimethyl-3-trimethylsilyloxy-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-17-yl]oxy-trimethylsilane 在 palladium diacetate 、 1,2-双(二苯基膦)乙烷 碳酸二稀丙酯 作用下， 以 苯甲腈 为溶剂， 以52%的产率得到3-hydroxy-5,15-androstadiene-17-one
  参考文献：
  名称：

  甲硅烷基烯醇醚，乙烯酮甲硅烷基缩醛和烯醇乙酸酯与碳酸烯丙酯的钯催化反应，合成α，β-不饱和酮，醛，酯和内酯的新方法

  摘要：

  通过使用钯-双（二苯基膦基）乙烷（dppe）用碳酸烯丙酯进行高收率处理，将由酮，醛，酯和内酯衍生的甲硅烷基烯醇醚和乙烯酮甲硅烷基缩醛转化为α，β-不饱和酮，醛，酯和内酯。 ）络合物作为催化剂。不含磷的钯催化剂代替钯-膦配合物为制备环戊烯酮，环辛烯酮，二烯酮，α，β-不饱和酯和内酯提供了更高的选择性。作为溶剂，必不可少的是使用乙腈等腈。在其他溶剂中，发生烯丙基化。通过使用钯配合物和甲醇三丁基锡作为双金属催化剂，通过与乙腈中的碳酸烯丙酯反应，将衍生自酮的烯醇乙酸酯转化为α，β-不饱和酮。

  DOI：

  10.1016/s0040-4020(01)90587-3
• 作为产物：
  描述：

  三氟甲磺酸三甲基硅酯 、 3-hydroxy-5-androsten-17-one 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 1.5h， 生成 [(8R,9S,10R,13S,14S)-10,13-dimethyl-3-trimethylsilyloxy-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-17-yl]oxy-trimethylsilane
  参考文献：
  名称：

  Site-selective fluorination of organic compounds using 1-alkyl-4-fluoro-1,4-diazabicyclo[2.2.2]octane salts (selectfluor reagents)

  摘要：

  The new ''N-F''-type electrophilic reagent family of 1-alkyl-4-fluoro-1,4-diazabicyclo[2.2.2]octane salts8d (derived from elemental fluorine (F2) and 1-alkyl-1,4-diazabicyclo[2.2.2]octane salts) has been found to be very effective for the fluorination of a wide variety of organic substrates. These include steroidal enol acetates and silyl enol ethers, phenyl-substituted olefins, sulfides bearing alpha-H atoms, certain carbanions, and mildly activated aromatic compounds. The products were obtained with good yields and regioselectivity under very mild reaction conditions.

  DOI：

  10.1021/jo00062a023

文献信息

• New synthetic methods for α,β -unsaturated ketones, aldehydes, esters and lactones by the palladium-catalyzed reactions of silyl enol ethers, ketene silyl acetals, and enol acetates with allyl carbonates
  作者：Ichiro Minami、Kazuhiko Takahashi、Isao Shimizu、Tsuneo Kimura、Jiro Tsuji

  DOI：10.1016/s0040-4020(01)90587-3

  日期：1986.1

  Silyl enol ethers and ketene silyl acetals derived from ketones, aldehydes, esters and lactones are converted into α,β-unsaturated ketones, aldehydes, esters and lactones by treatment with allyl carbonates in high yields using the palladium—bis(diphenylphosphino)ethane (dppe) complex as catalyst. Phosphine-free palladium catalyst instead of the palladium—phosphine complex gives a higher selectivity

  通过使用钯-双（二苯基膦基）乙烷（dppe）用碳酸烯丙酯进行高收率处理，将由酮，醛，酯和内酯衍生的甲硅烷基烯醇醚和乙烯酮甲硅烷基缩醛转化为α，β-不饱和酮，醛，酯和内酯。 ）络合物作为催化剂。不含磷的钯催化剂代替钯-膦配合物为制备环戊烯酮，环辛烯酮，二烯酮，α，β-不饱和酯和内酯提供了更高的选择性。作为溶剂，必不可少的是使用乙腈等腈。在其他溶剂中，发生烯丙基化。通过使用钯配合物和甲醇三丁基锡作为双金属催化剂，通过与乙腈中的碳酸烯丙酯反应，将衍生自酮的烯醇乙酸酯转化为α，β-不饱和酮。
• Site-selective fluorination of organic compounds using 1-alkyl-4-fluoro-1,4-diazabicyclo[2.2.2]octane salts (selectfluor reagents)
  作者：G. Sankar Lal

  DOI：10.1021/jo00062a023

  日期：1993.5

  The new ''N-F''-type electrophilic reagent family of 1-alkyl-4-fluoro-1,4-diazabicyclo[2.2.2]octane salts8d (derived from elemental fluorine (F2) and 1-alkyl-1,4-diazabicyclo[2.2.2]octane salts) has been found to be very effective for the fluorination of a wide variety of organic substrates. These include steroidal enol acetates and silyl enol ethers, phenyl-substituted olefins, sulfides bearing alpha-H atoms, certain carbanions, and mildly activated aromatic compounds. The products were obtained with good yields and regioselectivity under very mild reaction conditions.