2-Ethylsulfanyl-3-naphthalen-2-yl-propionic acid methyl ester | 165072-34-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-Ethylsulfanyl-3-naphthalen-2-yl-propionic acid methyl ester
• CAS: 165072-34-4
• 化学式: C₁₆H₁₈O₂S
• 分子量: 274.384
• InChiKey: GCQTXBJDEJVPJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.68
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-Ethylsulfanyl-3-naphthalen-2-yl-propionic acid methyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Searching for Minimum Increments of Hydrophobic Collapse: Flexible Dinaphthyl Carboxylates

  摘要：

  In an effort to identify minimal units of hydrophobically induced folding, we have examined flexible molecules containing two naphthyl moieties connected by a four-atom linker that also bears a carboxyl group. Crystallographic data show that the linkers allow intramolecular edge-to-face association of the naphthyl groups without excessive strain in the backbone. For the carboxylate forms of the dinaphthyl compounds, the occurrence of intramolecular naphthyl-naphthyl proximity in aqueous solution (24 degrees C) was detected via upfield shifts in the aromatic region H-1 NMR signals, relative to mononaphthyl control compounds. The naphthyl-naphthyl proximity does not appear to be strongly ''hydrophobically driven'', however, because similar upfield shifts (dinaphthyl vs mononaphthyl carboxylates) were observed in 8 M aqueous urea, and for the corresponding carboxylic acids in CDCl3 and C6D6. We conclude that these upfield shifts largely reflect chance encounters between the naphthyl groups resulting from random conformational motion.

  DOI：

  10.1021/ja00129a014
• 作为产物：
  描述：

  Methyl-3-(2-naphthyl)-acrylat 在 palladium on activated charcoal 盐酸 、 N,N-二甲基丙烯基脲 、 sodium hydroxide 、 氢气 、 lithium diisopropyl amide 作用下， 以 1,4-二氧六环 、 甲醇 、 乙酸乙酯 为溶剂， 25.0 ℃ 、275.79 kPa 条件下， 反应 5.0h， 生成 2-Ethylsulfanyl-3-naphthalen-2-yl-propionic acid methyl ester
  参考文献：
  名称：

  Searching for Minimum Increments of Hydrophobic Collapse: Flexible Dinaphthyl Carboxylates

  摘要：

  In an effort to identify minimal units of hydrophobically induced folding, we have examined flexible molecules containing two naphthyl moieties connected by a four-atom linker that also bears a carboxyl group. Crystallographic data show that the linkers allow intramolecular edge-to-face association of the naphthyl groups without excessive strain in the backbone. For the carboxylate forms of the dinaphthyl compounds, the occurrence of intramolecular naphthyl-naphthyl proximity in aqueous solution (24 degrees C) was detected via upfield shifts in the aromatic region H-1 NMR signals, relative to mononaphthyl control compounds. The naphthyl-naphthyl proximity does not appear to be strongly ''hydrophobically driven'', however, because similar upfield shifts (dinaphthyl vs mononaphthyl carboxylates) were observed in 8 M aqueous urea, and for the corresponding carboxylic acids in CDCl3 and C6D6. We conclude that these upfield shifts largely reflect chance encounters between the naphthyl groups resulting from random conformational motion.

  DOI：

  10.1021/ja00129a014