5,11,17,23-tetra-tert-butyl-25,26-dihydroxy-27,28-(1,4,7,10-tetraoxadecane-1,10-diyl)thiacalix[4]arene | 483342-38-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5,11,17,23-tetra-tert-butyl-25,26-dihydroxy-27,28-(1,4,7,10-tetraoxadecane-1,10-diyl)thiacalix[4]arene
• 英文别名: 3,9,15,21-Tetratert-butyl-25,28,31,34-tetraoxa-6,12,18,36-tetrathiahexacyclo[21.12.1.17,11.113,17.05,35.019,24]octatriaconta-1,3,5(35),7,9,11(38),13(37),14,16,19(24),20,22-dodecaene-37,38-diol
• CAS: 483342-38-7
• 化学式: C₄₆H₅₈O₆S₄
• 分子量: 835.227
• InChiKey: TWFHCYFKSITYHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.7
• 重原子数：
  56
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  179
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  5,11,17,23-tetra-tert-butyl-25,26-dihydroxy-27,28-(1,4,7,10-tetraoxadecane-1,10-diyl)thiacalix[4]arene 在 氢氧化钾 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 96.0h， 生成 syn-5,11,17,23-tetra-tert-butyl-25-hydroxy-26-hydroxycarbonylmethoxy-27,28-(1,4,7,10-tetraoxadecane-1,10-diyl)thiacalix[4]arene
  参考文献：
  名称：

  Synthesis of an inherently chiral O,O′-bridged thiacalix[4]crowncarboxylic acid and its application to a chiral solvating agent

  摘要：

  Treatment of readily available O,O'-1,1,3,3-tetraisopropyldisiloxane-1,3-diyl-bridged p-tert-butylthiacalix[4]arene (1) with tri(ethylene glycol) di-p-tosylate and subsequent desilylation gave O,O'-bridged thiacalix [4] crown 3 in an excellent yield. Mono-O-alkylation of 3 with ethyl bromoacetate, followed by optical resolution by chiral HPLC, and subsequent hydrolysis of the ester moiety gave inherently chiral O,O'-bridged thiacalix[4]crowncarboxylic acid (+)-6, which clearly discriminated enantiomeric primary amines, as well as amino esters, by H-1 NMR spectroscopy. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.074
• 作为产物：
  描述：

  三乙二醇二(对甲苯磺酸酯) 在 四丁基氟化铵 、 caesium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 31.0h， 生成 5,11,17,23-tetra-tert-butyl-25,26-dihydroxy-27,28-(1,4,7,10-tetraoxadecane-1,10-diyl)thiacalix[4]arene
  参考文献：
  名称：

  First synthesis of 25,26-bridged thiacalix[4]crowns by the use of a 25,26-O-disiloxanediyl-capped p-tert-butylthiacalix[4]arene

  摘要：

  通过用以下物质处理容易获得的 25,26-O-四异丙基二硅氧烷二基封端的对叔丁基 thiacalix[4] 芳烃 (3)，首次简便地合成了 25,26-桥联 thiacalix[4] 冠 (2a-f)。双官能烷基化剂 (5a–f) 和随后的脱甲硅烷基化。

  DOI：

  10.1039/b206050g

文献信息

• First synthesis of 25,26-bridged thiacalix[4]crowns by the use of a 25,26-O-disiloxanediyl-capped p-tert-butylthiacalix[4]arene
  作者：Fumitaka Narumi、Nobuji Matsumura、Naoya Morohashi、Hiroshi Kameyama、Sotaro Miyano

  DOI：10.1039/b206050g

  日期：2002.8.8

  The first and facile synthesis of 25,26-bridged thiacalix[4]crowns (2a–f) is disclosed by treatment of readily available 25,26-O-tetraisopropyldisiloxanediyl-capped p-tert-butylthiacalix[4]arene (3) with difunctional alkylating agents (5a–f) and subsequent desilylation.

  通过用以下物质处理容易获得的 25,26-O-四异丙基二硅氧烷二基封端的对叔丁基 thiacalix[4] 芳烃 (3)，首次简便地合成了 25,26-桥联 thiacalix[4] 冠 (2a-f)。双官能烷基化剂 (5a–f) 和随后的脱甲硅烷基化。
• Synthesis of an inherently chiral O,O′-bridged thiacalix[4]crowncarboxylic acid and its application to a chiral solvating agent
  作者：Fumitaka Narumi、Tetsutaro Hattori、Nobuji Matsumura、Toru Onodera、Hiroshi Katagiri、Chizuko Kabuto、Hiroshi Kameyama、Sotaro Miyano

  DOI：10.1016/j.tet.2004.06.074

  日期：2004.8

  Treatment of readily available O,O'-1,1,3,3-tetraisopropyldisiloxane-1,3-diyl-bridged p-tert-butylthiacalix[4]arene (1) with tri(ethylene glycol) di-p-tosylate and subsequent desilylation gave O,O'-bridged thiacalix [4] crown 3 in an excellent yield. Mono-O-alkylation of 3 with ethyl bromoacetate, followed by optical resolution by chiral HPLC, and subsequent hydrolysis of the ester moiety gave inherently chiral O,O'-bridged thiacalix[4]crowncarboxylic acid (+)-6, which clearly discriminated enantiomeric primary amines, as well as amino esters, by H-1 NMR spectroscopy. (C) 2004 Elsevier Ltd. All rights reserved.