methyl 1-(1-hydroxyethyl)cyclohexanecarboxylate | 72335-92-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: methyl 1-(1-hydroxyethyl)cyclohexanecarboxylate
• 英文别名: methyl 1-(1-hydroxyethyl)-cyclohexyl-carboxylate；Methyl 1-(1-hydroxyethyl)cyclohexane-1-carboxylate
• CAS: 72335-92-3
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: MRTULELNUACCPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 1-(1-hydroxyethyl)cyclohexanecarboxylate 在 lithium aluminium tetrahydride 、 正丁基锂 、 triphenylmethylium hexachloroantimonate(V) 、 三乙胺 、 pyridinium chlorochromate 、 三氟乙酸 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 50.25h， 生成 methyl 3(SR)-hydroxy-4-<1-<1(SR)-(mesitylthio)ethyl>cyclohexyl>-2,2-dimethylbutyrate
  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：

  环己甲酸甲酯 、 乙醛 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以74%的产率得到methyl 1-(1-hydroxyethyl)cyclohexanecarboxylate
  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

文献信息

• US4283420A
  申请人：——

  公开号：US4283420A

  公开（公告）日：1981-08-11