allyltrityldimethylsilane | 177658-58-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: allyltrityldimethylsilane
• 英文别名: tritylallyldimethylsilane；allyldimethyltritylsilane；Dimethyl-prop-2-enyl-tritylsilane
• CAS: 177658-58-1
• 化学式: C₂₄H₂₆Si
• 分子量: 342.556
• InChiKey: UXUGMLBQUSCROA-UHFFFAOYSA-N

物化性质

• 熔点：
  86-89 °C
• 沸点：
  414.2±14.0 °C(Predicted)
• 密度：
  0.989±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.45
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  allyltrityldimethylsilane 在 四丁基氟化铵 、 四氯化钛 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 1-[(1R,3R)-3-(Methoxy-dimethyl-silanyl)-cyclopentyl]-3,3-dimethyl-butan-1-one
  参考文献：
  名称：

  Tritylallyldimethylsilane−TiCl₄ Annulations to Electron Deficient Olefins. Diastereomerically Pure 3-Substituted and 3,4-Disubstituted Cyclopentanols

  摘要：

  DOI：

  10.1021/jo9601021
• 作为产物：
  描述：

  二甲基三苯甲基溴硅烷 、 氯丙烯镁 以 四氢呋喃 为溶剂， 反应 12.0h， 以77%的产率得到allyltrityldimethylsilane
  参考文献：
  名称：

  Allyldimethyltritylsilane. Synthesis of Cyclopentanols, Oxetanes, and Tetrahydrofurans by Reaction with Electron Deficient Olefins

  摘要：

  Allyldimethyltritylsilane (ADTS, 1) has been employed to access a variety of cyclopentanols via Lewis acid mediated annulation to electron deficient olefins. The intermediate silylcyclopentanes were converted to their respective cyclopentanols under mild, nonepimerizing oxidative conditions. In addition, ADTS undergoes efficient annulation onto aldehydes to provide oxetanes and tetrahydrofurans. Same preliminary investigations of this annulation to chiral nonracemic bicyclic lactams are presented.

  DOI：

  10.1021/jo9805652

文献信息

• Stereoselective Synthesis of Tetrahydropyrans via Formal [4 + 2]-Cycloaddition:  A Comparison of Allylsilane and Crotylsilane
  作者：Steven R. Angle、Dominique S. Belanger、Nahla A. El-Said

  DOI：10.1021/jo0203342

  日期：2002.11.1

  two diastereomers with allylsilane, but only a single diastereomer was observed in the case of crotylsilanes. The reaction time for crotylsilanes was longer than that for allylsilanes likely due to the increased steric hindrance. Allylsilanes afforded tetrahydropyrans in 34-67% yields, and crotylsilanes provided products in 0-62% yields.

  描述了一系列β-（三乙基甲硅烷氧基）醛与几种烯丙基硅烷和巴豆基二甲基苯基硅烷的反应。具有α-立体中心的醛以两种非对映异构体与烯丙基硅烷的混合物形式提供四氢吡喃，但是在巴豆基硅烷的情况下仅观察到单一的非对映异构体。巴豆硅烷的反应时间长于烯丙基硅烷的反应时间，这可能是由于空间位阻增加所致。烯丙基硅烷以34-67％的产率提供四氢吡喃，而巴豆基硅烷以0-62％的产率提供产物。
• Stereoselective Synthesis of Tetrahydropyrans via a Formal [4 + 2]-Cycloaddition of Allylsilanes
  作者：Steven R. Angle、Nahla A. El-Said

  DOI：10.1021/ja991861e

  日期：1999.11.1
• Allyldimethyltritylsilane: construction of enantiomerically pure cyclobutano[c]fused pyrrolidines
  作者：Michael D Groaning、Gregory P Brengel、A.I Meyers

  DOI：10.1016/s0040-4020(01)00083-7

  日期：2001.3

  Cyclobutannulation of the bicyclic lactam with allyldimethyltritylsilane is accomplished in high yield with good diastereoselectivity. The resulting tricyclic system is converted to a enantiomerically pure cyclobutane-fused pyrrolidine. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Allyldimethyltritylsilane. Synthesis of Cyclopentanols, Oxetanes, and Tetrahydrofurans by Reaction with Electron Deficient Olefins
  作者：Michael D. Groaning、Gregory P. Brengel、A. I. Meyers

  DOI：10.1021/jo9805652

  日期：1998.8.1

  Allyldimethyltritylsilane (ADTS, 1) has been employed to access a variety of cyclopentanols via Lewis acid mediated annulation to electron deficient olefins. The intermediate silylcyclopentanes were converted to their respective cyclopentanols under mild, nonepimerizing oxidative conditions. In addition, ADTS undergoes efficient annulation onto aldehydes to provide oxetanes and tetrahydrofurans. Same preliminary investigations of this annulation to chiral nonracemic bicyclic lactams are presented.
• Tritylallyldimethylsilane−TiCl₄ Annulations to Electron Deficient Olefins. Diastereomerically Pure 3-Substituted and 3,4-Disubstituted Cyclopentanols
  作者：Gregory P. Brengel、A. I. Meyers

  DOI：10.1021/jo9601021

  日期：1996.1.1