3,5-bis(methoxymethyloxy)benzyl thiol | 943139-47-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,5-bis(methoxymethyloxy)benzyl thiol
• 英文别名: [3,5-Bis(methoxymethoxy)phenyl]methanethiol；[3,5-bis(methoxymethoxy)phenyl]methanethiol
• CAS: 943139-47-7
• 化学式: C₁₁H₁₆O₄S
• 分子量: 244.312
• InChiKey: NWVUMSKUMATNIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  37.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,5-bis(methoxymethyloxy)benzyl thiol 在 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 1,3,5-tris((3,5-dihydroxybenzylthio)methyl)benzene
  参考文献：
  名称：

  Macrotricycles Featuring a π-Basic Tetrahedral Cavity:  Preference for NH₄⁺ Detected by Electrospray Ionization Mass Spectrometry

  摘要：

  Cation-pi interactions play an important role in biology. The title compounds are C-3-symmetric macrotricycles built from resorcinol, a pi electron-rich arene. They were prepared in up to 18% yield by intramolecular cyclization of 1,3,5-trisubstituted benzene tripods bearing pendant resorcinol groups, with methylene acetal bridges. Positive ESI-MS showed that these receptors recognize NH4+ over K+, and poorly respond to the large t-BuNH3+ cation, suggesting that they bind NH4+ intramolecularly, presumably via cation-pi interactions.

  DOI：

  10.1021/ol070498a
• 作为产物：
  描述：

  S-[3,5-bis(methoxymethoxy)benzyl] thioacetate 在 lithium aluminium tetrahydride 、 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以100%的产率得到3,5-bis(methoxymethyloxy)benzyl thiol
  参考文献：
  名称：

  Macrotricycles Featuring a π-Basic Tetrahedral Cavity:  Preference for NH₄⁺ Detected by Electrospray Ionization Mass Spectrometry

  摘要：

  Cation-pi interactions play an important role in biology. The title compounds are C-3-symmetric macrotricycles built from resorcinol, a pi electron-rich arene. They were prepared in up to 18% yield by intramolecular cyclization of 1,3,5-trisubstituted benzene tripods bearing pendant resorcinol groups, with methylene acetal bridges. Positive ESI-MS showed that these receptors recognize NH4+ over K+, and poorly respond to the large t-BuNH3+ cation, suggesting that they bind NH4+ intramolecularly, presumably via cation-pi interactions.

  DOI：

  10.1021/ol070498a

文献信息

• Macrotricycles Featuring a π-Basic Tetrahedral Cavity:  Preference for NH₄⁺ Detected by Electrospray Ionization Mass Spectrometry
  作者：Anne Lélias-Vanderperre、Jean-Claude Chambron、Enrique Espinosa、Peran Terrier、Emmanuelle Leize-Wagner

  DOI：10.1021/ol070498a

  日期：2007.8.1

  Cation-pi interactions play an important role in biology. The title compounds are C-3-symmetric macrotricycles built from resorcinol, a pi electron-rich arene. They were prepared in up to 18% yield by intramolecular cyclization of 1,3,5-trisubstituted benzene tripods bearing pendant resorcinol groups, with methylene acetal bridges. Positive ESI-MS showed that these receptors recognize NH4+ over K+, and poorly respond to the large t-BuNH3+ cation, suggesting that they bind NH4+ intramolecularly, presumably via cation-pi interactions.