2,2-diphenyl-2,3,4,5,6,7-hexahydro-2-sila-1H-indene | 144241-81-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 2,2-diphenyl-2,3,4,5,6,7-hexahydro-2-sila-1H-indene
• 英文别名: 2,2-diphenyl-1,3,4,5,6,7-hexahydrobenzo[c]silole；2,2-Diphenyl-1,3,4,5,6,7-hexahydro-2-benzosilole
• CAS: 144241-81-6
• 化学式: C₂₀H₂₂Si
• 分子量: 290.48
• InChiKey: FOQGNYKGUCRBID-UHFFFAOYSA-N

物化性质

• 沸点：
  393.0±35.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.13
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2,2-diphenyl-2,3,4,5,6,7-hexahydro-2-sila-1H-indene 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到2,2-diphenyl-1,3,4,5,6,7-hexahydro-7a-oxo-benzo[c]silole
  参考文献：
  名称：

  硅酮的Diels-Alder化学及其转化为Cyclohex-2-ene-1,4-顺式二醇

  摘要：

  描述了具有与天然产物合成连续的取代模式的硅醇盐的合成。通过热反应，路易斯酸和高压反应探索了它们在Diels-Alder化学中的反应性。此外，双环加合物被氧化裂解以显示高度官能化的环己烯核心。

  DOI：

  10.1021/ol101453e
• 作为产物：
  描述：

  1,2-二甲撑环己烷 在 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 7.5h， 生成 2,2-diphenyl-2,3,4,5,6,7-hexahydro-2-sila-1H-indene
  参考文献：
  名称：

  One-step spiroannulation using 1,2-bis(methylene)cycloalkane-magnesium reagents

  摘要：

  A one-step method for the synthesis of a wide variety of spirocyclic systems has been developed based on the reactions of bis-electrophiles with a series of new 1,3-diene-magnesium reagents, the magnesium complexes of 1,2-bis(methylene)cycloalkanes. The direct metalation of 1,2-bis(methylene)cycloalkanes with highly reactive magnesium in THF at ambient temperature generates the corresponding diene-magnesium reagents in high yields. Reactions of the diene-magnesium reagents with 1,n-dibromoalkanes produce a large number of spirocarbocycles containing an exocyclic double bond. The ring sizes of the accessible spiro compounds can be any combinations of four- to seven-membered rings. In most cases, the initially alkylated intermediates can be trapped by protonation, giving the corresponding bromo olefins. Significantly, treatment of the diene-magnesium reagents with bromoalkyl nitriles leads to a one-step synthesis of keto-functionalized spirocycles. The initial adduct is believed to be a Grignard reagent containing a cyano group. When a bromo nitrile containing a cyclic moiety is used as the bis-electrophile, the approach provides a direct access to dispiroenones.

  DOI：

  10.1021/jo00050a036

文献信息

• Diels−Alder Chemistry of Siloles and Their Transformation into Cyclohex-2-ene-1,4-<i>cis</i>-diols
  作者：Andrew C. Stevens、Brian L. Pagenkopf

  DOI：10.1021/ol101453e

  日期：2010.8.20

  The synthesis of siloles with substitution patterns that are continuative toward natural product synthesis are described. Their reactivity in Diels−Alder chemistry was explored through thermal, Lewis acid, and high-pressure reactions. Furthermore, bicyclic adducts were oxidatively cleaved to reveal a highly functionalized cyclohexene core.

  描述了具有与天然产物合成连续的取代模式的硅醇盐的合成。通过热反应，路易斯酸和高压反应探索了它们在Diels-Alder化学中的反应性。此外，双环加合物被氧化裂解以显示高度官能化的环己烯核心。
• One-step spiroannulation using 1,2-bis(methylene)cycloalkane-magnesium reagents
  作者：Reuben D. Rieke、Heping Xiong

  DOI：10.1021/jo00050a036

  日期：1992.11

  A one-step method for the synthesis of a wide variety of spirocyclic systems has been developed based on the reactions of bis-electrophiles with a series of new 1,3-diene-magnesium reagents, the magnesium complexes of 1,2-bis(methylene)cycloalkanes. The direct metalation of 1,2-bis(methylene)cycloalkanes with highly reactive magnesium in THF at ambient temperature generates the corresponding diene-magnesium reagents in high yields. Reactions of the diene-magnesium reagents with 1,n-dibromoalkanes produce a large number of spirocarbocycles containing an exocyclic double bond. The ring sizes of the accessible spiro compounds can be any combinations of four- to seven-membered rings. In most cases, the initially alkylated intermediates can be trapped by protonation, giving the corresponding bromo olefins. Significantly, treatment of the diene-magnesium reagents with bromoalkyl nitriles leads to a one-step synthesis of keto-functionalized spirocycles. The initial adduct is believed to be a Grignard reagent containing a cyano group. When a bromo nitrile containing a cyclic moiety is used as the bis-electrophile, the approach provides a direct access to dispiroenones.