2-(Naphthalen-2-ylmethylsulfanyl)-butyric acid | 165072-25-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(Naphthalen-2-ylmethylsulfanyl)-butyric acid
• 英文别名: 2-(Naphthalen-2-ylmethylsulfanyl)butanoic acid；2-(naphthalen-2-ylmethylsulfanyl)butanoic acid
• CAS: 165072-25-3
• 化学式: C₁₅H₁₆O₂S
• 分子量: 260.357
• InChiKey: SGPZMTRSRWUQHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(Naphthalen-2-ylmethylsulfanyl)-butyric acid 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 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：

  naphthalen-2-ylmethyl carbamimidothioate monohydrobromide 在 N,N-二甲基丙烯基脲 、 sodium hydroxide 、 碘 、 lithium diisopropyl amide 作用下， 反应 5.5h， 生成 2-(Naphthalen-2-ylmethylsulfanyl)-butyric acid
  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

文献信息

• Searching for Minimum Increments of Hydrophobic Collapse: Flexible Dinaphthyl Carboxylates
  作者：Lisa F. Newcomb、Tasir S. Haque、Samuel H. Gellman

  DOI：10.1021/ja00129a014

  日期：1995.6

  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.