4-(mesitylthio)pentanal | 164912-49-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-(mesitylthio)pentanal
• CAS: 164912-49-6
• 化学式: C₁₄H₂₀OS
• 分子量: 236.378
• InChiKey: BDZDHSVXORSAOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-甲氧基-1-(三甲基甲硅氧基)-2-甲基-1-丙烯 、 4-(mesitylthio)pentanal 在 triphenylmethylium hexachloroantimonate(V) 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 生成 methyl 3(RS)-hydroxy-6(SR)-mesitylthio-2,2-dimethylheptanone 、 methyl 3(SR)-hydroxy-6(SR)-mesitylthio-2,2-dimethylheptanone
  参考文献：
  名称：

  Remote asymmetric induction using neighboring group participation of a sulfenyl group

  摘要：

  2-[1-(Mesitylthio)alkyl]benzaldehydes and their dimethyl acetals react with silylated carbon nucleophiles under Lewis acidic conditions to give the corresponding aldol adducts with high diastereoselectivity, and in some cases, the products were obtained as almost a single diastereomer. Such a high diastereoselectivity is interpreted as the result of the 1,4-remote asymmetric induction through the benzene ring from the chiral ortho substituents of the substrates to the reaction centers. In the same manner, gamma-mesitylthiolated aliphatic aldehydes and their acetals also react diastereoselectively to give the corresponding aldol adducts. In this case, the remote asymmetric induction occurs without the aid of a rigid benzene ring on the main chain of the substrates. In both reactions, a 5-membered cyclic sulfonium ion intermediate is thought to exist in the reaction pathway, which is formed by the intramolecular S(N)2 reaction of the mesitylthio group, namely, the neighboring group participation of the sulfenyl group.

  DOI：

  10.1016/s0040-4020(01)85555-1
• 作为产物：
  描述：

  ethyl 3-(mesitylthio)butyrate 在 正丁基锂 、 二异丁基氢化铝 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 4-(mesitylthio)pentanal
  参考文献：
  名称：

  Remote asymmetric induction using neighboring group participation of a sulfenyl group

  摘要：

  2-[1-(Mesitylthio)alkyl]benzaldehydes and their dimethyl acetals react with silylated carbon nucleophiles under Lewis acidic conditions to give the corresponding aldol adducts with high diastereoselectivity, and in some cases, the products were obtained as almost a single diastereomer. Such a high diastereoselectivity is interpreted as the result of the 1,4-remote asymmetric induction through the benzene ring from the chiral ortho substituents of the substrates to the reaction centers. In the same manner, gamma-mesitylthiolated aliphatic aldehydes and their acetals also react diastereoselectively to give the corresponding aldol adducts. In this case, the remote asymmetric induction occurs without the aid of a rigid benzene ring on the main chain of the substrates. In both reactions, a 5-membered cyclic sulfonium ion intermediate is thought to exist in the reaction pathway, which is formed by the intramolecular S(N)2 reaction of the mesitylthio group, namely, the neighboring group participation of the sulfenyl group.

  DOI：

  10.1016/s0040-4020(01)85555-1