2-Benzyl-3-trimethylsilylpropene | 105941-67-1

• 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: 2-Benzyl-3-trimethylsilylpropene
• 英文别名: (2-benzylallyl)trimethylsilane；Silane, trimethyl[2-(phenylmethyl)-2-propenyl]-；2-benzylprop-2-enyl(trimethyl)silane
• CAS: 105941-67-1
• 化学式: C₁₃H₂₀Si
• 分子量: 204.387
• InChiKey: AJRSFHYDAJWRIV-UHFFFAOYSA-N

物化性质

• 沸点：
  251.1±19.0 °C(Predicted)
• 密度：
  0.868±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.12
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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-Benzyl-3-trimethylsilylpropene 在 四氯化锡 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 50.0h， 生成 (4S,5R)-4-benzyl-5-(2-benzylprop-3-enyl)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine
  参考文献：
  名称：

  Allyltrichlorostannane Additions to α-Amino Aldehydes: Application to the Total Synthesis of the Aspartyl Protease Inhibitorsl-682,679,l-684,414,l-685,434, andl-685,458

  摘要：

  羟基亚乙基二肽等排体l-682,679、l-684,414、l-685,434和l-685,458通过一系列步骤合成，包括与α-氨基醛的烯丙基三氯锡烷偶联、相应的1,2-顺式和1,2-反式氨基醇的氢硼化反应生成二醇、在TPAP条件下内酯化、内酯开环以及与所需胺或二肽酰胺的肽偶联。这种合成方法为其他大量二肽等排体的制备提供了一条实用的途径。

  DOI：

  10.1055/s-2003-37649
• 作为产物：
  描述：

  2,2-dibromostyrene 在 palladium diacetate 、 4-甲基苯磺酸吡啶 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 乙腈 为溶剂， 反应 48.0h， 生成 2-Benzyl-3-trimethylsilylpropene
  参考文献：
  名称：

  Preparation of 2-trimethylsilylmethyl-1-alkene; cross-coupling and protodesilylation sequence from 1,1-dibromo-1-alkene

  摘要：

  A new method for the preparation of exomethylene type allylsilane is described. Selective mono-protodesilylation of 1-trimethylsityl-2-trimethylsilylmethyl-2-alkenes 2 with PPTS afforded 2-trimethylsilylmethyl-l-alkeiles 4 in excellent yields. Since the resulting allylsilanes 4 possess an exomethylene unit, the reactions of 4 with carbonyl compounds in the presence of Lewis acids gave the corresponding product 7 having an exomethylene unit in excellent yields. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.12.044

文献信息

• Organozinc reagents in synthesis: the facile generation of 2-(trialkylsilyl)prop-2-enylzinc from 2-bromo-1-trimethylsilylprop-2-ene
  作者：James J. Eshelby、Philip J. Parsons、Patrick J. Crowley

  DOI：10.1039/p19960000191

  日期：——

  A range of electrophiles react with 2-(trimethylsilyl)prop-2-enylzinc chloride, which is prepared by sequentially treating 2-bromo-1-trimethylsilylprop-2-ene with ButLi and then zinc chloride. The addition of transition metal catalysts can alter the reactivity of the organometallic compound from prop-2-enylation to prop-1-en-2-ylation.

  一系列亲电体可与 2-(三甲基硅基)丙-2-烯基氯化锌发生反应，而 2-(三甲基硅基)丙-2-烯基氯化锌是先用丁锂处理 2-溴-1-三甲基硅基丙-2-烯，然后再用氯化锌处理 2-溴-1-三甲基硅基丙-2-烯。过渡金属催化剂的加入可以改变有机金属化合物的反应活性，使其从丙-2-烯基化反应转变为丙-1-烯-2-基化反应。
• Allyltrichlorostannane additions to chiral dipeptide aldehydes
  作者：Luiz C Dias、Edı́lson Ferreira

  DOI：10.1016/s0040-4039(01)01502-7

  日期：2001.10

  The first examples of successful allylsilane additions to chiral dipeptide aldehydes are described. Treatment of allylsilanes with tin tetrachloride at room temperature affords allyltrichlorostarnnane intermediates that reacts with dipeptide aldehydes to give 1,2-syn-homoallylic alcohols, potential intermediates for the synthesis of hydroxyethylene dipeptide isosteres. (C) 2001 Elsevier Science Ltd. All rights reserved.
• An efficient procedure for the synthesis of 2-N-Boc-amino-3,5-diols
  作者：Luiz C. Dias、Juliana Fattori、Carla C. Perez、Vanda M. de Oliveira、Andrea M. Aguilar

  DOI：10.1016/j.tet.2008.04.049

  日期：2008.6

  AWe wish to describe here the diastereoselective reaction between chiral N-Boc-alpha-amino aldehydes with both achiral allyltrichlorostannanes leading to 1,2-syn-N-Boc-alpha-amino alcohols, which are easily converted to the corresponding 4-N-Boc-amino-3-hydroxy ketones after treatment with catalytic amounts of OsO4 in the presence of NaIO4. After reduction of the carbonyl function, these 4-N-Boc-amino-3-hydroxy ketones were converted to 1-deoxy-5-hydroxy sphingosine analogues. (C) 2008 Elsevier Ltd. All rights reserved.
• Addition of allyltrichlorostannanes to aldehydes: application in the synthesis of 4-N-Boc-amino-3-hydroxy ketones
  作者：Luiz C. Dias、Juliana Fattori、Carla Cristina Perez

  DOI：10.1016/j.tetlet.2007.11.072

  日期：2008.1

  We wish to describe here the diastereoselective reaction between chiral N-Boc-alpha-amino aldehydes and achiral allyltrichlorostannanes leading to 1,2-syn-N-Boc-alpha-amino alcohols, which are treated with catalytic amounts of OSO4 in the presence of NaIO4 to provide the corresponding 4-N-Boc-amino-3-hydroxy ketones. (C) 2007 Elsevier Ltd. All rights reserved.
• Silyl-substituted π-allylnickel halides. A convenient synthesis of allylsilanes.
  作者：Gary A. Molander、David C. Shubert

  DOI：10.1016/s0040-4039(00)84101-5

  日期：1986.1