(Z)-α-(2-chloroethyl)cinnamaldehyde | 143008-11-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 英文名称: (Z)-α-(2-chloroethyl)cinnamaldehyde
• 英文别名: (2Z)-2-benzylidene-4-chlorobutanal
• CAS: 143008-11-1
• 化学式: C₁₁H₁₁ClO
• 分子量: 194.661
• InChiKey: OUWZOQJFDDYTDF-FLIBITNWSA-N

物化性质

• 沸点：
  337.1±37.0 °C(Predicted)
• 密度：
  1.132±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  苯甲醛二乙缩醛 在 盐酸 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 43.5h， 生成 (Z)-α-(2-chloroethyl)cinnamaldehyde
  参考文献：
  名称：

  Additions of 1-(.alpha.-alkoxybenzyl)benzotriazoles to enol ethers. New routes to 1,3-diethers

  摘要：

  1-(alpha-Alkoxybenzyl)benzotriazoles undergo reversible ionization in solution to a benzotriazolyl anion (Bt-) and carboxonium cations PhCH:O+R. These cations can attack the beta-carbon atom of enol ethers to give cation adducts which add the Bt- to form new alpha-(benzotriazol-1-yl)alkyl ethers in which the carbon chains are extended by an alpha-ethoxybenzyl group. Reactions of these adducts with Grignard reagents produce the corresponding 1,3-diethers in high yield. Reduction of the adducts with lithium aluminum hydride gives the corresponding diethers via substitution of the benzotriazolyl moiety with a hydrogen atom or 1-(3-alkoxyalkyl)benzotriazoles via substitution of the alpha-alkoxy group, depending on the reaction conditions and the nature of the adduct.

  DOI：

  10.1021/jo00044a030

文献信息

• Additions of 1-(.alpha.-aminoalkyl)benzotriazoles to enol ethers. New routes to 1,3-amino ethers
  作者：Alan R. Katritzky、Stanislaw Rachwal、Bogumila Rachwal、Peter J. Steel

  DOI：10.1021/jo00044a031

  日期：1992.8

  1-(alpha-Aminoalkyl)benzotriazoles add readily to enol ethers to give the corresponding 1-benzotriazolyl-3-aminoalkyl ethers in high yields. Subsequent replacement of the benzotriazole moiety by an alkyl or aryl group (with a Grignard reagent) or by a hydrogen atom (with lithium aluminum hydride) affords 1,3-amino-ethers in good yields. Anchimeric assistance by the amino groups in the substitutions of the benzotriazolyl moiety facilitates the reactions. Full stereochemistry is assigned to the stereoisomeric products on the basis of NMR techniques and X-ray diffraction.
• Additions of 1-(.alpha.-alkoxybenzyl)benzotriazoles to enol ethers. New routes to 1,3-diethers
  作者：Alan R. Katritzky、Stanislaw Rachwal、Bogumila Rachwal、Peter J. Steel

  DOI：10.1021/jo00044a030

  日期：1992.8

  1-(alpha-Alkoxybenzyl)benzotriazoles undergo reversible ionization in solution to a benzotriazolyl anion (Bt-) and carboxonium cations PhCH:O+R. These cations can attack the beta-carbon atom of enol ethers to give cation adducts which add the Bt- to form new alpha-(benzotriazol-1-yl)alkyl ethers in which the carbon chains are extended by an alpha-ethoxybenzyl group. Reactions of these adducts with Grignard reagents produce the corresponding 1,3-diethers in high yield. Reduction of the adducts with lithium aluminum hydride gives the corresponding diethers via substitution of the benzotriazolyl moiety with a hydrogen atom or 1-(3-alkoxyalkyl)benzotriazoles via substitution of the alpha-alkoxy group, depending on the reaction conditions and the nature of the adduct.