allyl(bromomethyl)dimethylsilane | 32367-49-0

• 分子结构分类: 有机化合物 - 有机盐 - 有机金属盐
• 英文名称: allyl(bromomethyl)dimethylsilane
• 英文别名: Bromomethyl-dimethyl-prop-2-enylsilane
• CAS: 32367-49-0
• 化学式: C₆H₁₃BrSi
• 分子量: 193.159
• InChiKey: KCRSPOZVPOFERM-UHFFFAOYSA-N

物化性质

• 沸点：
  154.1±15.0 °C(Predicted)
• 密度：
  1.125±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.81
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  allyl(bromomethyl)dimethylsilane 在 偶氮二异丁腈 、 氢溴酸 作用下， 以 正戊烷 为溶剂， 生成 γ-Brompropyl-brommethyl-dimethylsilan
  参考文献：
  名称：

  WO2006/66872

  摘要：

  公开号：
• 作为产物：
  描述：

  溴甲基二甲基氯硅烷 、 氯丙烯镁 在 盐酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 allyl(bromomethyl)dimethylsilane
  参考文献：
  名称：

  WO2006/66872

  摘要：

  公开号：

文献信息

• Zinc mediated allylations of chlorosilanes promoted by ultrasound: Synthesis of novel constrained sila amino acids
  作者：Remya Ramesh、D. Srinivasa Reddy

  DOI：10.1039/c4ob00294f

  日期：——

  A simple, fast and efficient method for allylation and propargylation of chlorosilanes through zinc mediation and ultrasound promotion is reported. As a direct application of the resulting bis-allylsilanes, three novel, constrained sila amino acids are prepared for the first time.

  通过锌介导和超声波促进，报道了一种用于氯硅烷的烯基化和丙炔基化的简单、快速和高效方法。作为产生的双烯基硅烷的直接应用，首次制备了三种新颖的约束硅氨基酸。
• Chiral organosilicon compounds in organic synthesis II. Enantioselective synthesis of homoallylic alcohols
  作者：T.H. Chan、D. Wang

  DOI：10.1016/s0040-4039(00)99397-3

  日期：1989.1

  Condensations of – with aldehydes under Lewis acid conditions give optically active homoallylic alcohols with enantiomeric excess of up to 50%. The results are discussed in terms of competition between antiperiplanar and synclinal transition states.

  -在路易斯酸条件下与-醛的缩合反应生成对映体过量高达50％的旋光均丙醇。根据反周平面和向斜过渡状态之间的竞争来讨论结果。
• Regioselective Fluorohydrin Synthesis from Allylsilanes and Evidence for a Silicon–Fluorine Gauche Effect
  作者：Alexie W. Clover、Adam P. Jones、Robert F. Berger、Werner Kaminsky、Gregory. W. O’Neil

  DOI：10.1021/acs.joc.3c02163

  日期：2024.4.5

  conditions (e.g., higher reaction temperature), opening of allylsilane-derived epoxides with this reagent occurs at room temperature. We attribute this rate acceleration along with the observed regioselectivity to a β-silyl effect that stabilizes a proposed cationic intermediate. The use of enantioenriched epoxides indicates that both SN1- and SN2-type mechanisms may be operable depending on substitution at

  使用环氧化序列，然后用HF·Et 3 N处理，分离或不分离中间体环氧化物，可以将烯丙基硅烷以良好的收率区域选择性地转化为相应的3-甲硅烷基氟代醇。可以容忍各种硅取代，从而通过该方法产生一系列 2-氟-3-甲硅烷基丙-1-醇产品。然而使用HF·Et 3 N通过环氧化物开环合成其他氟代醇通常需要更多的强制条件（例如，更高的反应温度），而用该试剂对烯丙基硅烷衍生的环氧化物的开环发生在室温下。我们将这种速率加速以及观察到的区域选择性归因于稳定所提出的阳离子中间体的β-甲硅烷基效应。对映体富集环氧化物的使用表明，S N 1 型和S N 2 型机制均可根据硅上的取代而起作用。通过 NMR 和理论进行的构象分析以及通过 X 射线衍射获得的晶体结构表明，硅和氟在产品中倾向于彼此接近，这可能是由于静电相互作用而受到青睐。
• Catalytic Enantioselective Cyclization/Cross-Coupling with Alkyl Electrophiles
  作者：Huan Cong、Gregory C. Fu

  DOI：10.1021/ja500706v

  日期：2014.3.12

  As part of our ongoing effort to expand the scope of cross-coupling reactions of alkyl electrophiles, we have pursued a strategy wherein the nucleophilic coupling partner includes a pendant olefin; after transmetalation by such a substrate, if beta-migratory insertion proceeds faster than direct cross-coupling, an additional carbon carbon bond and stereocenter can be formed. With the aid of a nickel/diamine catalyst (both components are commercially available), we have established the viability of this approach for the catalytic asymmetric synthesis of 2,3-dihydrobenzofurans and indanes. Furthermore, we have applied this new method to the construction of the dihydrobenzofuran core of fasiglifam, as well as to a cross-coupling with a racemic alkyl electrophile; in the latter process, the chiral catalyst controls two stereocenters, one that is newly generated in a beta-migratory insertion and one that begins as a mixture of enantiomers.
• Transannular interactions of the silyl center with distant keto groups in the mass spectra of medium-sized organosilicon heterocycles. Improved synthetic routes to six-, seven-, and eight-membered silicon ring systems
  作者：William P. Weber、Raymond A. Felix、Alvin K. Willard、Richard M. Laine、Heinz G. Boettger

  DOI：10.1021/jo00825a012

  日期：1971.12