(+/-)-(E)-2-benzhydryldimethylsilyl-3-pentene | 274676-37-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+/-)-(E)-2-benzhydryldimethylsilyl-3-pentene
• 英文别名: benzhydryl-dimethyl-[(E)-pent-3-en-2-yl]silane
• CAS: 274676-37-8
• 化学式: C₂₀H₂₆Si
• 分子量: 294.512
• InChiKey: AMBNNERMIXJAMS-LFYBBSHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.03
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• 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：

  氯磺酰异氰酸酯 、 (+/-)-(E)-2-benzhydryldimethylsilyl-3-pentene 在 sodium sulfite 作用下， 以 甲苯 、 二氯甲烷 为溶剂， 反应 22.0h， 以88%的产率得到(3S*,4R*,5S*)-4-benzhydryldimethylsilyl-3,5-dimethyl-2-pyrrolidinone
  参考文献：
  名称：

  Benzhydryldimethylsilyl Allylic Silanes:  Syntheses and Applications to [3 + 2] Annulation Reactions

  摘要：

  A new silyl group, the benzhydryldimethylsilyl group, has been developed that is easily synthesized and that undergoes facile oxidation. The [3 + 2] annulation reactions of allylic silanes with this silyl group provide a variety of highly substituted five-membered carbocycles and heterocycles with high stereoselectivities. The silyl groups of these cyclic compounds have been oxidized to hydroxyl groups to demonstrate the general synthetic utility of the method.

  DOI：

  10.1021/ol005676d
• 作为产物：
  描述：

  benzhydryldimethylchlorosilane 在 正丁基锂 、 dimethyl sulfide borane 、 环己烯 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 28.16h， 生成 (+/-)-(E)-2-benzhydryldimethylsilyl-3-pentene
  参考文献：
  名称：

  Benzhydryldimethylsilyl Allylic Silanes:  Syntheses and Applications to [3 + 2] Annulation Reactions

  摘要：

  A new silyl group, the benzhydryldimethylsilyl group, has been developed that is easily synthesized and that undergoes facile oxidation. The [3 + 2] annulation reactions of allylic silanes with this silyl group provide a variety of highly substituted five-membered carbocycles and heterocycles with high stereoselectivities. The silyl groups of these cyclic compounds have been oxidized to hydroxyl groups to demonstrate the general synthetic utility of the method.

  DOI：

  10.1021/ol005676d

文献信息

• Stereoselective Synthesis of Substituted γ-Butyrolactones by the [3 + 2] Annulation of Allylic Silanes with Chlorosulfonyl Isocyanate:  Enantioselective Total Synthesis of (+)-Blastmycinone
  作者：Zhi-Hui Peng、K. A. Woerpel

  DOI：10.1021/ol0069960

  日期：2001.3.1

  [GRAPHICS]A stereoselective synthesis of gamma -butyrolactones by the [3 + 2] annulation of allylic silanes with N-chlorosulfonyl isocyanate (CSI) was developed. An enantioselective total synthesis of (+)-blastmycinone was accomplished using this annulation as the key step.
• Benzhydryldimethylsilyl Allylic Silanes:  Syntheses and Applications to [3 + 2] Annulation Reactions
  作者：Zhi-Hui Peng、K. A. Woerpel

  DOI：10.1021/ol005676d

  日期：2000.5.1

  A new silyl group, the benzhydryldimethylsilyl group, has been developed that is easily synthesized and that undergoes facile oxidation. The [3 + 2] annulation reactions of allylic silanes with this silyl group provide a variety of highly substituted five-membered carbocycles and heterocycles with high stereoselectivities. The silyl groups of these cyclic compounds have been oxidized to hydroxyl groups to demonstrate the general synthetic utility of the method.