3,6,9,12,20,23,26,29,35,36-Decaaza-tricyclo[29.3.1.1^14,18]hexatriaconta-1(35),14,16,18(36),31,33-hexaene-2,13,19,30-tetraone | 905733-22-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: 3,6,9,12,20,23,26,29,35,36-Decaaza-tricyclo[29.3.1.1^14,18]hexatriaconta-1(35),14,16,18(36),31,33-hexaene-2,13,19,30-tetraone
• 英文别名: 3,6,9,12,20,23,26,29,35,36-Decazatricyclo[29.3.1.114,18]hexatriaconta-1(35),14(36),15,17,31,33-hexaene-2,13,19,30-tetrone；3,6,9,12,20,23,26,29,35,36-decazatricyclo[29.3.1.114,18]hexatriaconta-1(35),14(36),15,17,31,33-hexaene-2,13,19,30-tetrone
• CAS: 905733-22-4
• 化学式: C₂₆H₃₈N₁₀O₄
• 分子量: 554.652
• InChiKey: KBNIKJJVIKLNNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  40
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  190
• 氢给体数：
  8
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3,6,9,12,20,23,26,29,35,36-Decaaza-tricyclo[29.3.1.1^14,18]hexatriaconta-1(35),14,16,18(36),31,33-hexaene-2,13,19,30-tetraone 、 聚合甲醛 在 甲酸 作用下， 以 水 为溶剂， 以34%的产率得到6,9,23,26-Tetramethyl-3,6,9,12,20,23,26,29,35,36-decazatricyclo[29.3.1.114,18]hexatriaconta-1(35),14(36),15,17,31,33-hexaene-2,13,19,30-tetrone
  参考文献：
  名称：

  Anion and Carboxylic Acid Binding to Monotopic and Ditopic Amidopyridine Macrocycles

  摘要：

  Binding of inorganic anions, carboxylic acids, and tetraalkylammonium carboxylates by macrocyclic compounds of different size was studied by NMR in DMSO-d(6). It has been shown that at least a 15-membered ring is necessary for successful recognition of fluoride. Larger macrocycles were shown to bind HSO(4)(-), H(2)PO(4)(-), Cl(-), and carboxylic acid salts. Effects of binding topicity are discussed. The 30-membered macrocycles 4 and 4m selectively bind substrates that are size- and shape-complementary: maximum binding is observed for dicarboxylic acids and dicarboxylates with four-carbon chains, and the binding constant for association of fumaric acid and 4 is ca. 5 orders of magnitude higher than that of maleic acid. The 30-membered macrocycle 4m showed selectivity toward alpha-ketocarboxylic acids. Secondary amino groups were not crucial for binding of fluoride to the macrocycles; however, they proved to be very important for selectivity and strength of carboxylic acid binding. The X-ray structure of the adduct of 4 and nitrobenzoic acid confirmed the guest H-bonding with both the amide and the secondary amino groups of the 30-membered macrocyclic host.

  DOI：

  10.1021/jo800128r
• 作为产物：
  描述：

  三乙烯四胺 以 甲醇 为溶剂， 反应 24.0h， 生成 3,6,9,12,20,23,26,29,35,36-Decaaza-tricyclo[29.3.1.1^14,18]hexatriaconta-1(35),14,16,18(36),31,33-hexaene-2,13,19,30-tetraone
  参考文献：
  名称：

  与单和双位大环酰胺结合的阴离子。

  摘要：

  [结构：见正文]在DMSO-d6中通过NMR研究了不同大小的大环化合物与氟阴离子以及羧酸四烷基铵盐的结合。已经发现，成功识别氟化物至少需要一个15元环。在[2 + 2]环化中获得的较大的大环化合物显示与二羧酸盐结合。讨论了绑定主题的影响。

  DOI：

  10.1021/ol060786r

文献信息

• Anion Binding to Monotopic and Ditopic Macrocyclic Amides
  作者：Ivan V. Korendovych、Mimi Cho、Phillip L. Butler、Richard J. Staples、Elena V. Rybak-Akimova

  DOI：10.1021/ol060786r

  日期：2006.7.1

  [Structure: see text] Binding of fluoride anion as well as carboxylic acid tetraalkylammonium salts by macrocyclic compounds of different size was studied by NMR in DMSO-d6. It has been found that at least a 15-membered ring is necessary for successful recognition of fluoride. Larger macrocycles obtained in a [2+2] cyclization were shown to bind dicarboxylic acid salts. Effects of binding topicity

  [结构：见正文]在DMSO-d6中通过NMR研究了不同大小的大环化合物与氟阴离子以及羧酸四烷基铵盐的结合。已经发现，成功识别氟化物至少需要一个15元环。在[2 + 2]环化中获得的较大的大环化合物显示与二羧酸盐结合。讨论了绑定主题的影响。
• Anion and Carboxylic Acid Binding to Monotopic and Ditopic Amidopyridine Macrocycles
  作者：Ivan V. Korendovych、Mimi Cho、Olga V. Makhlynets、Phillip L. Butler、Richard J. Staples、Elena V. Rybak-Akimova

  DOI：10.1021/jo800128r

  日期：2008.7.1

  Binding of inorganic anions, carboxylic acids, and tetraalkylammonium carboxylates by macrocyclic compounds of different size was studied by NMR in DMSO-d(6). It has been shown that at least a 15-membered ring is necessary for successful recognition of fluoride. Larger macrocycles were shown to bind HSO(4)(-), H(2)PO(4)(-), Cl(-), and carboxylic acid salts. Effects of binding topicity are discussed. The 30-membered macrocycles 4 and 4m selectively bind substrates that are size- and shape-complementary: maximum binding is observed for dicarboxylic acids and dicarboxylates with four-carbon chains, and the binding constant for association of fumaric acid and 4 is ca. 5 orders of magnitude higher than that of maleic acid. The 30-membered macrocycle 4m showed selectivity toward alpha-ketocarboxylic acids. Secondary amino groups were not crucial for binding of fluoride to the macrocycles; however, they proved to be very important for selectivity and strength of carboxylic acid binding. The X-ray structure of the adduct of 4 and nitrobenzoic acid confirmed the guest H-bonding with both the amide and the secondary amino groups of the 30-membered macrocyclic host.