(E)-3-(Triethylsilyl)-2-propenal | 21207-54-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-3-(Triethylsilyl)-2-propenal
• 英文别名: (E)-3-triethylsilylpropenal；3t-Triaethylsilyl-acrylaldehyd；(E)-3-triethylsilylprop-2-enal
• CAS: 21207-54-5
• 化学式: C₉H₁₈OSi
• 分子量: 170.327
• InChiKey: RBGZJJCZKLAAQU-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-3-(Triethylsilyl)-2-propenal 在 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 生成 α-Triaethylsilylacrylsaeure
  参考文献：
  名称：

  Triethylsilylacrylic acids

  摘要：

  DOI：

  10.1007/bf00932110
• 作为产物：
  描述：

  3-(三乙基甲硅烷基)-2-丙炔-1-醇 在 manganese(IV) oxide 、 红铝 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 12.0h， 生成 (E)-3-(Triethylsilyl)-2-propenal
  参考文献：
  名称：

  Catalytic Asymmetric Addition of Polyfunctional Dialkylzincs to .beta.-Stannylated and .beta.-Silylated Unsaturated Aldehydes

  摘要：

  The addition of functionalized dialkylzincs to readily available beta-stannylated or beta-silylated unsaturated aldehydes in the presence of a catalytic amount of (1R,2R)-1,2-bis(trifluorosulfonamido)cyclohexane (8 mol%) provides chiral allylic alcohols in good yields (60-90%) and excellent enantioselectivity (usually in the range of 85-95% ee). The synthetic utility of these allylic alcohols as chiral building blacks is demonstrated. The gamma-stannylated allylic alcohols were submitted to a Stille coupling leading to polyfunctional allylic alcohols and gamma-alkoxy enones. A treatment with CuCN in N-methylpyrrolidone at 130 degrees C provided chiral unsaturated gamma-hydroxy nitriles. Finally, the desilylation of the gamma-silylated alcohols gave chiral allylic alcohols having a terminal double bond. The catalytic asymmetric addition was found to show an important inverse temperature dependance. A mechanism for this addition is proposed.

  DOI：

  10.1021/jo00094a027

文献信息

• Synthesis of Heterocyclic Quinones by Aza-Diels-Alder Reaction of a 4-Stannyl-1-azadiene
  作者：Juan Cuerva、Antonio Echavarren

  DOI：10.1055/s-1997-735

  日期：1997.2

  4-Stannyl-1-azadiene 2 undergoes aza-Diels-Alder reactions with activated dienophiles. Selective oxidation of the adducts proceeds with allylic inversion allowing for the efficient preparation of new heterocyclic quinones.

  4-Stannyl-1-azadiene 2 与活化的亲二烯体发生 aza-Diels-Alder 反应。加合物的选择性氧化通过烯丙基反转进行，从而可以有效制备新的杂环醌。
• Komarov,N.V. et al., Journal of general chemistry of the USSR, 1968, vol. 38, p. 2035 - 2038
  作者：Komarov,N.V. et al.

  DOI：——

  日期：——
• Ostwald Roswitha, Chavant Pierre-Yves, Stadtmueller Heinz, Knochel Paul, J. Org. Chem., 59 (1994) N 15, S 4143-4153
  作者：Ostwald Roswitha, Chavant Pierre-Yves, Stadtmueller Heinz, Knochel Paul

  DOI：——

  日期：——
• Catalytic Asymmetric Addition of Polyfunctional Dialkylzincs to .beta.-Stannylated and .beta.-Silylated Unsaturated Aldehydes
  作者：Roswitha Ostwald、Pierre-Yves Chavant、Heinz Stadtmueller、Paul Knochel

  DOI：10.1021/jo00094a027

  日期：1994.7

  The addition of functionalized dialkylzincs to readily available beta-stannylated or beta-silylated unsaturated aldehydes in the presence of a catalytic amount of (1R,2R)-1,2-bis(trifluorosulfonamido)cyclohexane (8 mol%) provides chiral allylic alcohols in good yields (60-90%) and excellent enantioselectivity (usually in the range of 85-95% ee). The synthetic utility of these allylic alcohols as chiral building blacks is demonstrated. The gamma-stannylated allylic alcohols were submitted to a Stille coupling leading to polyfunctional allylic alcohols and gamma-alkoxy enones. A treatment with CuCN in N-methylpyrrolidone at 130 degrees C provided chiral unsaturated gamma-hydroxy nitriles. Finally, the desilylation of the gamma-silylated alcohols gave chiral allylic alcohols having a terminal double bond. The catalytic asymmetric addition was found to show an important inverse temperature dependance. A mechanism for this addition is proposed.
• Triethylsilylacrylic acids
  作者：M. G. Voronkov、S. V. Kirpichenko、V. V. Keiko、E. O. Tsetlina

  DOI：10.1007/bf00932110

  日期：1973.8