(dioctyl)acetyl[7-(dioctyl)acetylamino-1,8-naphthyridin-2-yl]amide | 773891-79-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: (dioctyl)acetyl[7-(dioctyl)acetylamino-1,8-naphthyridin-2-yl]amide
• 英文别名: 2-octyl-N-[7-(2-octyldecanoylamino)-1,8-naphthyridin-2-yl]decanamide
• CAS: 773891-79-5
• 化学式: C₄₄H₇₆N₄O₂
• 分子量: 693.113
• InChiKey: QCGGVCKCOICCRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17
• 重原子数：
  50
• 可旋转键数：
  32
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  84
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (dioctyl)acetyl[7-(dioctyl)acetylamino-1,8-naphthyridin-2-yl]amide 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 以75%的产率得到N-(7-amino-1,8-naphthyridin-2-yl)-2-octyldecanamide
  参考文献：
  名称：

  Self-assembly of a new series of quadruply hydrogen bonded heterotrimers driven by the donor–acceptor interaction

  摘要：

  This paper describes the self-assembly of a new series of heterotrimers in chloroform-d by utilizing the cooperative interaction of hydrogen bonding and donor-acceptor interaction. Compounds 1 and 11, in which an 2-ureido-4[1H]-pyrimidinone unit is connected to 34-crown-10 or 36-crown-10, were used as donor monomer, and 2 and 19, in which an 2-ureido-4[1H]-pyrimidinone unit is connected to NDI, were used as acceptor monomer, while linear compound 4, which contains two diamido-1,8-naphthyridines, was used as template. A large tri-p-(t-butyl)phenylmethoxyl group was introduced to 19 in order to compare its assembling behavior with that of 2. Mixing 4 with dimer 1 (.) 2 caused 1 (.) 2 to fully decompose and to afford 55% of 'in-in'-oriented heterotrimer 1 (.) 4 (.) 2. Adding 4 to the solution of 2 (.) 11 or 11 (.) 19 in chloroform-d also led to full dissociation of the dimers. However, in these systems the 'in-in'-arranged heterotrimer 2 (.) 4 (.) 11 or 11 (.) 4 (.) 19 could be produced exclusively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.07.075
• 作为产物：
  描述：

  2-octyldecanoyl chloride 、 1,8-萘啶-2,7-二胺 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 10.0h， 以67%的产率得到(dioctyl)acetyl[7-(dioctyl)acetylamino-1,8-naphthyridin-2-yl]amide
  参考文献：
  名称：

  Donor–acceptor interaction-mediated arrangement of hydrogen bonded dimers

  摘要：

  The donor-acceptor interaction-driven supramolecular arrangement of a new series of quadruply hydrogen-bonded homo- and heterodimers have been investigated in chloroform with H-1 NMR and UV-Vis spectroscopy. Two kinds of structurally complementary monomers have been prepared. Monomers 3 and 4 are incorporated with one ureidopyrimidone unit and one electron deficient pyromellitic diimide (PDI) or naphthalene diimide (NDI) unit, respectively, monomers 5 and 6 are incorporated with two ureidopyrimidone units and one PDI or NDI unit, respectively, whereas monomers 7 and 8 consist of one electron rich bis-p-phenylene[34]crown-10 unit and one or two 2,7-diamido-1,6-naphthyridine units, respectively. Compounds 3 and 4 exist exclusively as homodimers, respectively. Adding 1 equiv. of 7 to the solution of 3.3 and 4.4 induced them to partially or fully dissociate to produce heterodimers 3.7 and 4.7 due to intermolecular donor-acceptor interaction and the formation of a new binding mode between the ureidopyrimidone of 3 or 4 and the 2,7-diamido-1,6-naphthyridine unit of 7. Both 5 and 6 exist as cyclic monomer and dimer in chloroform. Adding 1 equiv. of 8 to the solution of 5 or 6 in chloroform caused all the cyclic dimer and most of the cyclic monomer to de-cyclize to form new heterodimers 5.8 and 6.8, respectively. H-1 NMR and UV-vis study revealed that heterodimer 5.8 has a structure in which the PDI of 5 is not threaded through the cavity of the bis-p-phenylene [34] crown-10 unit of 8. In contrast, in addition to the heterodimer similar to 5.8, about 40% of heterodimer 6.8 is generated, in which the PDI of 6 is threaded through the cavity of the bis-p-phenylene[3]crown-10 unit of 8 due to the increased donor-acceptor interaction between NDI and bis-p-phenylene [34] crown-10. Steric hindrance and mismatching of the hydrogen bonding moiety play important roles in the arrangement of the new homo- and heterodimers. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.104

文献信息

• Donor–acceptor interaction-mediated arrangement of hydrogen bonded dimers
  作者：Xiao-Qiang Li、Dai-Jun Feng、Xi-Kui Jiang、Zhan-Ting Li

  DOI：10.1016/j.tet.2004.06.104

  日期：2004.9

  The donor-acceptor interaction-driven supramolecular arrangement of a new series of quadruply hydrogen-bonded homo- and heterodimers have been investigated in chloroform with H-1 NMR and UV-Vis spectroscopy. Two kinds of structurally complementary monomers have been prepared. Monomers 3 and 4 are incorporated with one ureidopyrimidone unit and one electron deficient pyromellitic diimide (PDI) or naphthalene diimide (NDI) unit, respectively, monomers 5 and 6 are incorporated with two ureidopyrimidone units and one PDI or NDI unit, respectively, whereas monomers 7 and 8 consist of one electron rich bis-p-phenylene[34]crown-10 unit and one or two 2,7-diamido-1,6-naphthyridine units, respectively. Compounds 3 and 4 exist exclusively as homodimers, respectively. Adding 1 equiv. of 7 to the solution of 3.3 and 4.4 induced them to partially or fully dissociate to produce heterodimers 3.7 and 4.7 due to intermolecular donor-acceptor interaction and the formation of a new binding mode between the ureidopyrimidone of 3 or 4 and the 2,7-diamido-1,6-naphthyridine unit of 7. Both 5 and 6 exist as cyclic monomer and dimer in chloroform. Adding 1 equiv. of 8 to the solution of 5 or 6 in chloroform caused all the cyclic dimer and most of the cyclic monomer to de-cyclize to form new heterodimers 5.8 and 6.8, respectively. H-1 NMR and UV-vis study revealed that heterodimer 5.8 has a structure in which the PDI of 5 is not threaded through the cavity of the bis-p-phenylene [34] crown-10 unit of 8. In contrast, in addition to the heterodimer similar to 5.8, about 40% of heterodimer 6.8 is generated, in which the PDI of 6 is threaded through the cavity of the bis-p-phenylene[3]crown-10 unit of 8 due to the increased donor-acceptor interaction between NDI and bis-p-phenylene [34] crown-10. Steric hindrance and mismatching of the hydrogen bonding moiety play important roles in the arrangement of the new homo- and heterodimers. (C) 2004 Elsevier Ltd. All rights reserved.
• Self-assembly of a new series of quadruply hydrogen bonded heterotrimers driven by the donor–acceptor interaction
  作者：Xiao-Qiang Li、Mu-Xin Jia、Xiao-Zhong Wang、Xi-Kui Jiang、Zhan-Ting Li、Guang-Ju Chen、Yi-Hua Yu

  DOI：10.1016/j.tet.2005.07.075

  日期：2005.10

  This paper describes the self-assembly of a new series of heterotrimers in chloroform-d by utilizing the cooperative interaction of hydrogen bonding and donor-acceptor interaction. Compounds 1 and 11, in which an 2-ureido-4[1H]-pyrimidinone unit is connected to 34-crown-10 or 36-crown-10, were used as donor monomer, and 2 and 19, in which an 2-ureido-4[1H]-pyrimidinone unit is connected to NDI, were used as acceptor monomer, while linear compound 4, which contains two diamido-1,8-naphthyridines, was used as template. A large tri-p-(t-butyl)phenylmethoxyl group was introduced to 19 in order to compare its assembling behavior with that of 2. Mixing 4 with dimer 1 (.) 2 caused 1 (.) 2 to fully decompose and to afford 55% of 'in-in'-oriented heterotrimer 1 (.) 4 (.) 2. Adding 4 to the solution of 2 (.) 11 or 11 (.) 19 in chloroform-d also led to full dissociation of the dimers. However, in these systems the 'in-in'-arranged heterotrimer 2 (.) 4 (.) 11 or 11 (.) 4 (.) 19 could be produced exclusively. (c) 2005 Elsevier Ltd. All rights reserved.