3-[(trimethylsilyl)methyl]but-3-enyl 4-formylbenzoate | 494205-59-3

• 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: 3-[(trimethylsilyl)methyl]but-3-enyl 4-formylbenzoate
• 英文别名: 3-(Trimethylsilylmethyl)but-3-enyl 4-formylbenzoate；3-(trimethylsilylmethyl)but-3-enyl 4-formylbenzoate
• CAS: 494205-59-3
• 化学式: C₁₆H₂₂O₃Si
• 分子量: 290.434
• InChiKey: KACBIIQNCJGRNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.94
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-(三甲基甲硅烷基甲基)丁-3-烯酸 在 lithium aluminium tetrahydride 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 3-[(trimethylsilyl)methyl]but-3-enyl 4-formylbenzoate
  参考文献：
  名称：

  Asymmetric Polymer Synthesis by Repetitive SakuraiHosomi Allylation Reaction of Compounds Possessing Both Formyl and Allylsilane Functions

  摘要：

  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.

  DOI：

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

文献信息

• 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.