N'-phenyl-N-[2,9,16-tris-decyl-13,20-bis[(C-hydroxy-N-phenylcarbonimidoyl)amino]-3,10,17-trioxo-2,9,16-triazatetracyclo[16.3.1.14,8.111,15]tetracosa-1(22),4,6,8(24),11,13,15(23),18,20-nonaen-6-yl]carbamimidic acid | 1312807-31-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N'-phenyl-N-[2,9,16-tris-decyl-13,20-bis[(C-hydroxy-N-phenylcarbonimidoyl)amino]-3,10,17-trioxo-2,9,16-triazatetracyclo[16.3.1.14,8.111,15]tetracosa-1(22),4,6,8(24),11,13,15(23),18,20-nonaen-6-yl]carbamimidic acid
• CAS: 1312807-31-0
• 化学式: C₇₂H₉₃N₉O₆
• 分子量: 1180.59
• InChiKey: BJOWMQUVOVNLRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.8
• 重原子数：
  87
• 可旋转键数：
  36
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  195
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N'-phenyl-N-[2,9,16-tris-decyl-13,20-bis[(C-hydroxy-N-phenylcarbonimidoyl)amino]-3,10,17-trioxo-2,9,16-triazatetracyclo[16.3.1.14,8.111,15]tetracosa-1(22),4,6,8(24),11,13,15(23),18,20-nonaen-6-yl]carbamimidic acid 、 tetrabutylammonium tetrafluoroborate 以 氘代氯仿 为溶剂， 生成
  参考文献：
  名称：

  Calix[3]amide-based anion receptors: high affinity for fluoride ions and a twisted binding model

  摘要：

  Tris-phenylurea-substituted calix[3]amides (3a, 3b) and tris-phenylthiourea-substituted calix[3]amides (4a, 4b) were synthesised by the reaction of amine with isocyanates and thioisocyanate, respectively. Single crystal X-ray analysis revealed that the cyclic trimers adopt a syn conformation with all of the urea groups on the same side. The binding affinities of these compounds towards anions were measured using 1H NMR titrations in DMF-d7, DMSO-d6 or CDCl3. Each receptor was observed to bind halogen anions in a 1:1 stoichiometry, exclusively through hydrogen bonding, and the anion selectivity was in the order F- Cl->> Br- I-. DFT calculations revealed that the fluoride anion is anchored in the centre of the six N-H hydrogen atoms of 3a through H center dot center dot center dot F interactions.

  DOI：

  10.1080/10610278.2010.514909
• 作为产物：
  描述：

  1-碘癸烷 在 palladium on activated charcoal 、 氢气 、 chlorotriphenylphosphonium chloride 作用下， 以 六甲基磷酰三胺 、 乙醇 、 氯仿 、 1,1,2,2-四氯乙烷 为溶剂， 反应 35.0h， 生成 N'-phenyl-N-[2,9,16-tris-decyl-13,20-bis[(C-hydroxy-N-phenylcarbonimidoyl)amino]-3,10,17-trioxo-2,9,16-triazatetracyclo[16.3.1.14,8.111,15]tetracosa-1(22),4,6,8(24),11,13,15(23),18,20-nonaen-6-yl]carbamimidic acid
  参考文献：
  名称：

  Calix[3]amide-based anion receptors: high affinity for fluoride ions and a twisted binding model

  摘要：

  Tris-phenylurea-substituted calix[3]amides (3a, 3b) and tris-phenylthiourea-substituted calix[3]amides (4a, 4b) were synthesised by the reaction of amine with isocyanates and thioisocyanate, respectively. Single crystal X-ray analysis revealed that the cyclic trimers adopt a syn conformation with all of the urea groups on the same side. The binding affinities of these compounds towards anions were measured using 1H NMR titrations in DMF-d7, DMSO-d6 or CDCl3. Each receptor was observed to bind halogen anions in a 1:1 stoichiometry, exclusively through hydrogen bonding, and the anion selectivity was in the order F- Cl->> Br- I-. DFT calculations revealed that the fluoride anion is anchored in the centre of the six N-H hydrogen atoms of 3a through H center dot center dot center dot F interactions.

  DOI：

  10.1080/10610278.2010.514909

文献信息

• Calix[3]amide-based anion receptors: high affinity for fluoride ions and a twisted binding model
  作者：Kosuke Katagiri、Taniyuki Furuyama、Hyuma Masu、Takako Kato、Mio Matsumura、Masanobu Uchiyama、Aya Tanatani、Masahide Tominaga、Hiroyuki Kagechika、Kentaro Yamaguchi、Isao Azumaya

  DOI：10.1080/10610278.2010.514909

  日期：2011.1.1

  Tris-phenylurea-substituted calix[3]amides (3a, 3b) and tris-phenylthiourea-substituted calix[3]amides (4a, 4b) were synthesised by the reaction of amine with isocyanates and thioisocyanate, respectively. Single crystal X-ray analysis revealed that the cyclic trimers adopt a syn conformation with all of the urea groups on the same side. The binding affinities of these compounds towards anions were measured using 1H NMR titrations in DMF-d7, DMSO-d6 or CDCl3. Each receptor was observed to bind halogen anions in a 1:1 stoichiometry, exclusively through hydrogen bonding, and the anion selectivity was in the order F- Cl->> Br- I-. DFT calculations revealed that the fluoride anion is anchored in the centre of the six N-H hydrogen atoms of 3a through H center dot center dot center dot F interactions.