58-Bromo-12,40-dioxa-18,34-dithianonacyclo[40.2.2.27,10.213,16.220,23.229,32.236,39.12,6.124,28]octapentaconta-1(44),2(58),3,5,7(57),8,10(56),13(55),14,16(54),20(53),21,23(52),24,26,28(51),29,31,36,38,42,45,47,49-tetracosaene | 154488-19-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 58-Bromo-12,40-dioxa-18,34-dithianonacyclo[40.2.2.27,10.213,16.220,23.229,32.236,39.12,6.124,28]octapentaconta-1(44),2(58),3,5,7(57),8,10(56),13(55),14,16(54),20(53),21,23(52),24,26,28(51),29,31,36,38,42,45,47,49-tetracosaene
• CAS: 154488-19-4
• 化学式: C₅₄H₄₃BrO₂S₂
• 分子量: 867.97
• InChiKey: JLNADXRQMJFJNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14
• 重原子数：
  59
• 可旋转键数：
  0
• 环数：
  18.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  69.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  58-Bromo-12,40-dioxa-18,34-dithianonacyclo[40.2.2.27,10.213,16.220,23.229,32.236,39.12,6.124,28]octapentaconta-1(44),2(58),3,5,7(57),8,10(56),13(55),14,16(54),20(53),21,23(52),24,26,28(51),29,31,36,38,42,45,47,49-tetracosaene 在 盐酸 、 正丁基锂 作用下， 生成 12,40-Dioxa-18,34-dithianonacyclo[40.2.2.27,10.213,16.220,23.229,32.236,39.12,6.124,28]octapentaconta-1(44),2(58),3,5,7(57),8,10(56),13(55),14,16(54),20(53),21,23(52),24,26,28(51),29,31,36,38,42,45,47,49-tetracosaene
  参考文献：
  名称：

  Synthesis of Cyclophanes with Intra-Annular Functionality and Cage Structure

  摘要：

  Cyclophanes of the type 1 and 2, with large cavity sizes, have been synthesized from the corresponding dichloride 8 or 8a and o-xylene-alpha,alpha'-dithiol (9), p-xylene-alpha,alpha'-dithiol (10), or m-terphenyldithiol (11). Similarly, cyclophanes of the type 3 with intra-annular functionality have been obtained by the coupling of the corresponding dithiol 15 or 19 and m-terphenyl dibromide 5, 5a, 5b, or 5c. With the aim of introducing multifunctionality, cyclophanes of the type 21 and 23 were prepared from 3,5-bis(mercaptomethyl)anisole or 3,5-bis(mercaptomethyl)phenol and the corresponding substituted m-terphenyl dibromide Bb or 5c. Cyclophanes 24, 24a, 24b, and 32, with a new type of cage structure, have been obtained by the coupling of the corresponding tetrathiol as with 2 equiv of the dibromides 5c, 5a, and 5b or 1 equiv of the tetrabromide 31, respectively. Further, the sodium salts of the cyclophanes 3c, 21, and 24b were completely characterized by H-1 NMR spectroscopy. XRD analysis of the cyclophane 21 revealed the presence of an ethanol molecule inside the cavity, indicating the facile formation of a host-guest complex.

  DOI：

  10.1021/jo950957y
• 作为产物：
  描述：

  1,3-di(p-tolyl)benzene 在 氢氧化钾 、 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醇 、 苯 为溶剂， 反应 64.0h， 生成 58-Bromo-12,40-dioxa-18,34-dithianonacyclo[40.2.2.27,10.213,16.220,23.229,32.236,39.12,6.124,28]octapentaconta-1(44),2(58),3,5,7(57),8,10(56),13(55),14,16(54),20(53),21,23(52),24,26,28(51),29,31,36,38,42,45,47,49-tetracosaene
  参考文献：
  名称：

  Synthesis of Cyclophanes with Intra-Annular Functionality and Cage Structure

  摘要：

  Cyclophanes of the type 1 and 2, with large cavity sizes, have been synthesized from the corresponding dichloride 8 or 8a and o-xylene-alpha,alpha'-dithiol (9), p-xylene-alpha,alpha'-dithiol (10), or m-terphenyldithiol (11). Similarly, cyclophanes of the type 3 with intra-annular functionality have been obtained by the coupling of the corresponding dithiol 15 or 19 and m-terphenyl dibromide 5, 5a, 5b, or 5c. With the aim of introducing multifunctionality, cyclophanes of the type 21 and 23 were prepared from 3,5-bis(mercaptomethyl)anisole or 3,5-bis(mercaptomethyl)phenol and the corresponding substituted m-terphenyl dibromide Bb or 5c. Cyclophanes 24, 24a, 24b, and 32, with a new type of cage structure, have been obtained by the coupling of the corresponding tetrathiol as with 2 equiv of the dibromides 5c, 5a, and 5b or 1 equiv of the tetrabromide 31, respectively. Further, the sodium salts of the cyclophanes 3c, 21, and 24b were completely characterized by H-1 NMR spectroscopy. XRD analysis of the cyclophane 21 revealed the presence of an ethanol molecule inside the cavity, indicating the facile formation of a host-guest complex.

  DOI：

  10.1021/jo950957y

文献信息

• Synthesis of dithiacyclophanes with large molecular cavity
  作者：Perumal Rajakumar、Arunachalam Kannan

  DOI：10.1016/s0040-4039(00)79365-8

  日期：1993.7

  Coupling of the dichlorides 9 & 10 with xylenedithiols and m-terphenyldithiol under high dilution technique in presence of KOH in benzene-ethanol afforded the cyclophanes of the class 1 & 2.
• Synthesis of Cyclophanes with Intra-Annular Functionality and Cage Structure
  作者：Arunachalam Kannan、Perumal Rajakumar、V. Kabaleeswaran、S. S. Rajan

  DOI：10.1021/jo950957y

  日期：1996.1.1

  Cyclophanes of the type 1 and 2, with large cavity sizes, have been synthesized from the corresponding dichloride 8 or 8a and o-xylene-alpha,alpha'-dithiol (9), p-xylene-alpha,alpha'-dithiol (10), or m-terphenyldithiol (11). Similarly, cyclophanes of the type 3 with intra-annular functionality have been obtained by the coupling of the corresponding dithiol 15 or 19 and m-terphenyl dibromide 5, 5a, 5b, or 5c. With the aim of introducing multifunctionality, cyclophanes of the type 21 and 23 were prepared from 3,5-bis(mercaptomethyl)anisole or 3,5-bis(mercaptomethyl)phenol and the corresponding substituted m-terphenyl dibromide Bb or 5c. Cyclophanes 24, 24a, 24b, and 32, with a new type of cage structure, have been obtained by the coupling of the corresponding tetrathiol as with 2 equiv of the dibromides 5c, 5a, and 5b or 1 equiv of the tetrabromide 31, respectively. Further, the sodium salts of the cyclophanes 3c, 21, and 24b were completely characterized by H-1 NMR spectroscopy. XRD analysis of the cyclophane 21 revealed the presence of an ethanol molecule inside the cavity, indicating the facile formation of a host-guest complex.