二甲基三苯甲基溴硅烷 | 62092-85-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 中文名称: 二甲基三苯甲基溴硅烷
• 英文名称: trityldimethylsilylbromide
• 英文别名: dimethyltritylbromosilane；Trityldimethylbromosilane；bromo-dimethyl-tritylsilane
• CAS: 62092-85-7
• 化学式: C₂₁H₂₁BrSi
• 分子量: 381.387
• InChiKey: HMYFIHNULFGLHS-UHFFFAOYSA-N

物化性质

• 熔点：
  200-202°C
• 沸点：
  442.4±44.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.34
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 危险等级：
  8
• 危险品运输编号：
  UN 1759
• 海关编码：
  2931900090
• 包装等级：
  III
• 危险类别：
  8

反应信息

• 作为反应物：
  描述：

  二甲基三苯甲基溴硅烷 在 四氯化钛 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 1-[(1R,3R)-3-(Dimethyl-trityl-silanyl)-cyclopentyl]-3,3-dimethyl-butan-1-one
  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

• Exo-Selective Diels−Alder Reactions of Vinylazepines. Origin of Divergent Stereoselectivity in Diels−Alder Reactions of Vinylazepines, Vinylpiperideines, and Vinylcycloalkenes
  作者：Brant Boren、Jennifer S. Hirschi、Joseph H. Reibenspies、Matthew D. Tallant、Daniel A. Singleton、Gary A. Sulikowski

  DOI：10.1021/jo034462h

  日期：2003.11.1

  Diels-Alder reactions of vinylazepines with N-phenylmaleimide afforded exclusively the exo cycloadduct, while high endo stereoselectivity was observed, as previously reported, in analogous reactions of vinylpiperideines. This curious contrast was confirmed by X-ray analysis of cycloadducts not susceptible to epimerization. The stereoselectivity of Diels-Alder reactions of vinylazepines, vinylpiperideines

  乙烯基氮杂s与N-苯基马来酰亚胺的狄尔斯-阿尔德反应仅提供环外加成，而如先前报道的，在乙烯基哌啶的类似反应中观察到高的内消旋立体选择性。通过对不易发生差向异构化的环加合物进行X射线分析，证实了这种奇怪的对比。乙烯基氮杂环庚烷，乙烯基哌啶和乙烯基环烯烃的Diels-Alder反应的立体选择性表现出令人惊讶的差异，这取决于详细的二烯结构，并通过DFT计算（Becke3LYP）阐明了这些发现。模型计算可以正确预测这些反应中的主要立体异构体，尽管它们往往会大大低估立体选择性。
• Enantioselective Strategy to the Spirocyclic Core of Palau'amine and Related Bisguanidine Marine Alkaloids
  作者：Anja S. Dilley、Daniel Romo

  DOI：10.1021/ol015864j

  日期：2001.5.1

  enantioselective strategy to the spirocyclic core found in the oroidin-derived family of bisguanidine marine alkaloids has been devised, premised on a biosynthetic proposal. Herein, we describe the successful implementation of this strategy, which entails a Diels-Alder reaction and a chlorination/ring contraction sequence that delivers the fully functionalized spirocyclic core. In this initial report, an intermolecular

  [结构：见正文]在生物合成方案的基础上，已设计出一种对映体选择性策略，该策略是在源自鸟苷的双胍海洋生物碱家族中发现的螺环核心。在本文中，我们描述了该策略的成功实施，该策略涉及Diels-Alder反应和提供完全功能化螺环核心的氯化/环收缩序列。在该初始报告中，分子间氯化反应生成的环戊烷在C17处相对于帕劳胺而言是异构体，在C11时相对于乙酰丙胺而言是异构体。
• A unified synthetic strategy toward oroidin-derived alkaloids premised on a biosynthetic proposal
  作者：Paul J. Dransfield、Anja S. Dilley、Shaohui Wang、Daniel Romo

  DOI：10.1016/j.tet.2005.12.068

  日期：2006.5

  Details of the evolution of a synthetic strategy toward the spirocyclic chlorocyclopentane core of oroidin-derived alkaloids, including the axinellamines and potentially adaptable to palau'amine, are described. A proposed refinement of the Kinnel-Scheuer biosynthetic proposal for palau'amine is posited. Studies undertaken to improve the regioselectivity and efficiency of a key Diels-Alder reaction utilizing a novel protecting group strategy, microwave chemistry, and other strategies are described. Further insights regarding the suitability of different protecting groups during the epoxidation/chlorination/ring contraction sequence are disclosed. Several interesting by-products from this reaction sequence are reported. These studies have led to a unified synthetic strategy to the axinellamines and palau'amine. (c) 2006 Elsevier Ltd. All rights reserved.
• Intramolecular, Nucleophile-Catalyzed Aldol-Lactonization (NCAL) Reactions:  Catalytic, Asymmetric Synthesis of Bicyclic β-Lactones
  作者：Guillermo S. Cortez、Reginald L. Tennyson、Daniel Romo

  DOI：10.1021/ja016134+

  日期：2001.8.1
• 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.