S-[3,5-bis(methoxymethoxy)benzyl] thioacetate | 943139-46-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: S-[3,5-bis(methoxymethoxy)benzyl] thioacetate
• 英文别名: 3,5-bis(methoxymethyloxy)benzyl thiolacetate；S-[[3,5-bis(methoxymethoxy)phenyl]methyl] ethanethioate
• CAS: 943139-46-6
• 化学式: C₁₃H₁₈O₅S
• 分子量: 286.349
• InChiKey: DIMBLZNYNWPUGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  79.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  S-[3,5-bis(methoxymethoxy)benzyl] thioacetate 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 1,3,5-triethyl-2,4,6-tris((3,5-bis(methoxymethyloxy)benzylthio)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：

  3,5-双(甲氧基甲基氧)苄醇 、 硫代乙酸 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以77%的产率得到S-[3,5-bis(methoxymethoxy)benzyl] thioacetate
  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

• <i>C</i>₃<i>_v</i>-Symmetrical Tribenzotriquinacenes Extended by Six C₁-Functional Groups and the First Triquinacene-Based Tris(dithiametacyclophanes)
  作者：Ling Zhou、Tao-Xiang Zhang、Bing-Rui Li、Xiao-Ping Cao、Dietmar Kuck

  DOI：10.1021/jo070565e

  日期：2007.8.1

  The first examples of novel bowl-shaped tribenzotriquinacenes (TBTQs) bearing three dithiametacyclophane units within their arene peripheries are reported. The synthesis is based on a C3v-symmetrical hexakis(chloromethyl)tribenzotriquinacene as the key intermediate and yields the inter-ring metacyclophane-type macrocyclization instead of the intra-ring orthocyclophane-type cyclocondensation. Multiple

  据报道，新颖的碗形三苯并三喹硫酮（TBTQs）在其芳烃周围带有三个二硫代甲环烷单元的第一个例子。综合基于C 3 v-对称的六（氯甲基）三苯并三喹并苯为主要中间体，并产生环间的metaphanphane型大环化，而不是环内的orthocyclophane型环缩合。相同关键中间体的多次亲核取代会导致许多其他新的6倍官能化的三苯并三苯并二氢呋喃，其中一些作为构建新型碗形有机网络的易于获得的构建基可能是令人感兴趣的。通过X射线分析确定了新型的三（二硫代间环已烷）以及六（氯甲基）-和六（羟甲基）三苯并三苯并蒽的分子结构，并讨论了固体中有趣的主体/客体聚集和扭转效应。