4-{1-[(trimethylsilyl)methyl]ethenyl}benzaldehyde | 137190-14-8

• 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: 4-{1-[(trimethylsilyl)methyl]ethenyl}benzaldehyde
• 英文别名: 4-(3-Trimethylsilylprop-1-en-2-yl)benzaldehyde
• CAS: 137190-14-8
• 化学式: C₁₃H₁₈OSi
• 分子量: 218.371
• InChiKey: FSHWBWAQWLKPON-UHFFFAOYSA-N

物化性质

• 沸点：
  299.1±28.0 °C(Predicted)
• 密度：
  0.940±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.85
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  甲基4-甲酰苯甲酸酯二缩醛 在 cerium(III) chloride 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 为溶剂， 生成 4-{1-[(trimethylsilyl)methyl]ethenyl}benzaldehyde
  参考文献：
  名称：

  Asymmetric Synthesis of Chiral Polymers by Means of Repetitive Addition of Allylsilane to Aldehyde

  摘要：

  制备了同时具有烯丙基三甲基硅氧基和甲酰基的单体。采用手性（酰氧基）硼烷启动单体的重复聚加反应，得到具有主链构型手性的光学活性聚合物。通过对降解产物的分析评估了手性聚合物的光学纯度。

  DOI：

  10.1055/s-2002-28502

文献信息

• Ionic Liquid-Promoted, Highly Regioselective Heck Arylation of Electron-Rich Olefins by Aryl Halides
  作者：Jun Mo、Lijin Xu、Jianliang Xiao

  DOI：10.1021/ja0450861

  日期：2005.1.1

  arylation reaction in molecular solvents led to mixtures of regioisomers under similar conditions. Several lines of evidence point to the unique regiocontrol stemming from the ionic environment provided by the ionic liquid that alters the reaction pathway. The chemistry provides a simple, effective method for preparing branched, arylated olefins and contributes to the extension of Heck reaction to a wider

  钯催化的富电子烯烃、乙烯基醚 1a-d、烯酰胺 1e-g 和烯丙基三甲基硅烷 1h 的区域选择性 Heck 芳基化已在咪唑鎓离子液体中完成，使用范围广泛的芳基溴化物和碘化物代替常用的芳基溴化物和碘化物，但市售且昂贵的芳基三氟甲磺酸酯。该反应以高效率和显着的区域选择性进行，不需要昂贵或有毒的卤化物清除剂，仅导致 1a-g 杂原子的烯烃碳和 1a-g 杂原子的 β 被具有不同电子和空间性质的芳基取代。 1小时。相比之下，分子溶剂中的芳基化反应在类似条件下导致区域异构体的混合物。几条证据表明独特的区域控制源于离子液体提供的离子环境，它改变了反应途径。该化学反应为制备支化、芳基化烯烃提供了一种简单、有效的方法，并有助于将 Heck 反应扩展到更广泛的底物。
• Asymmetric Polymer Synthesis by Repetitive SakuraiHosomi Allylation Reaction of Compounds Possessing Both Formyl and Allylsilane Functions
  作者：Shinichi Itsuno、Toshihiro Kumagai

  DOI：10.1002/1522-2675(200210)85:10<3185::aid-hlca3185>3.0.co;2-b

  日期：2002.10

  Trialkylallylsilanes generally react with aldehydes in the presence of a Lewis acid to the corresponding homoallylic alcohols. Chiral Lewis acids promote the same reaction to yield the enantiomerically-enriched homoallylalcohols. We have prepared four compounds (7-10) that possess both formyl and allylsilane functions. Lewis acids initiated self-polyaddition reactions of these compounds by means of repetitive allylation. The use of chiral Lewis acids resulted in the formation of optically active polymers that possess exo-methylene and secondary OH functions in their main chain. The optical purity of these chiral polymers was estimated based on the results of model asymmetric reactions between benzaldehyde and beta-substituted allylsilanes and by controlled degradation.
• Synthesis of functionalized allylsilanes via palladium-catalyzed cross-coupling of 2-stannyl-3-silylpropene with organic halides.
  作者：Kyung-Tae Kang、Soung Sin Kim、Jae Chul Lee

  DOI：10.1016/s0040-4039(00)92165-8

  日期：1991.1

  Allylsilanes bearing the various functionalities were prepared from the palladium-catalyzed cross-coupling reactions of 2-trimethylstannyl-3-trimethylsilylpropene with acid chlorides and with aryl halides.
• Asymmetric Synthesis of Chiral Polymers by Means of Repetitive Addition of Allylsilane to Aldehyde
  作者：Shinichi Itsuno、Toshihiro Kumagai

  DOI：10.1055/s-2002-28502

  日期：——

  Monomers having both allyltrimethylsilyl and formyl groups were prepared. Chiral (acyloxy)borane initiated the repetitive polyaddition of the monomers to give optically active polymers having main chain configurational chirality. Optical purity of the chiral polymer was evaluated by the analysis of the degradation product.

  制备了同时具有烯丙基三甲基硅氧基和甲酰基的单体。采用手性（酰氧基）硼烷启动单体的重复聚加反应，得到具有主链构型手性的光学活性聚合物。通过对降解产物的分析评估了手性聚合物的光学纯度。