7-tert-Butoxycarbonylamino-2-chloro-[1,8]naphthyridine-3-carboxylic acid ethyl ester | 213680-84-3

• 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: 7-tert-Butoxycarbonylamino-2-chloro-[1,8]naphthyridine-3-carboxylic acid ethyl ester
• 英文别名: Ethyl 2-chloro-7-[(2-methylpropan-2-yl)oxycarbonylamino]-1,8-naphthyridine-3-carboxylate
• CAS: 213680-84-3
• 化学式: C₁₆H₁₈ClN₃O₄
• 分子量: 351.79
• InChiKey: OJPJPDNZHQEHEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  90.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7-tert-Butoxycarbonylamino-2-chloro-[1,8]naphthyridine-3-carboxylic acid ethyl ester 在 18-冠醚-6 、 potassium carbonate 、 三氟乙酸 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 、 叔丁醇 为溶剂， 反应 28.33h， 生成 7-[3,5-Bis-(3,5-di-tert-butyl-benzyloxy)-benzylamino]-2-ethylamino-3H-1,3,8,9-tetraaza-anthracen-4-one
  参考文献：
  名称：

  Supramolecular Polymer Chemistry:  Self-Assembling Dendrimers Using the DDA·AAD (GC-like) Hydrogen Bonding Motif

  摘要：

  Heterocyclic unit 2 containing complementary donor-donor-acceptor (DDA) and acceptor-acceptor-donor (AAD) hydrogen bonding arrays at an angle of about 601 Was designed to self-assemble into a hexamer. To investigate whether this unit could self-assemble dendrimers, the 2,8-diamino-2-N-ethylpyrimido-(4,5-b)(1, 8)naphthyridine-3H-4-one subunit was synthesized with a first (2a), second (2b), and third generation (2c) Frechet-type dendron attached to the 8-amino group. The synthesis of 2a-c was accomplished in 11 steps beginning with 2,6-diaminopyridine and the corresponding dendron bromide. Studies using H-1 NMR, size exclusion chromatography (SEC), and dynamic light scattering (DLS) support the cooperative formation of cyclic hexamers in apolar solvents. The stability of the self-assembled dendrimers is dependent on the size of the attached dendron, and mixing studies with 2a-c indicate their usefulness in constructing dynamic combinatorial libraries.

  DOI：

  10.1021/ja0202006
• 作为产物：
  描述：

  7-Amino-3-carbethoxy-1,8-naphthyridin-2(1H)-one 在 吡啶 、 4-二甲氨基吡啶 、 乙醇 、 potassium carbonate 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 55.0h， 生成 7-tert-Butoxycarbonylamino-2-chloro-[1,8]naphthyridine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Supramolecular Polymer Chemistry:  Self-Assembling Dendrimers Using the DDA·AAD (GC-like) Hydrogen Bonding Motif

  摘要：

  Heterocyclic unit 2 containing complementary donor-donor-acceptor (DDA) and acceptor-acceptor-donor (AAD) hydrogen bonding arrays at an angle of about 601 Was designed to self-assemble into a hexamer. To investigate whether this unit could self-assemble dendrimers, the 2,8-diamino-2-N-ethylpyrimido-(4,5-b)(1, 8)naphthyridine-3H-4-one subunit was synthesized with a first (2a), second (2b), and third generation (2c) Frechet-type dendron attached to the 8-amino group. The synthesis of 2a-c was accomplished in 11 steps beginning with 2,6-diaminopyridine and the corresponding dendron bromide. Studies using H-1 NMR, size exclusion chromatography (SEC), and dynamic light scattering (DLS) support the cooperative formation of cyclic hexamers in apolar solvents. The stability of the self-assembled dendrimers is dependent on the size of the attached dendron, and mixing studies with 2a-c indicate their usefulness in constructing dynamic combinatorial libraries.

  DOI：

  10.1021/ja0202006

文献信息

• Chiral eighteen-component three-dimensional supramolecular entities stabilized by the hydrogen bonding and coordination interactions
  作者：Shi-Gui Chen、Yong-Chun Fu、Gui-Tao Wang、Guang-Yu Li、Yuguo Ma、Xi-Kui Jiang、Zhan-Ting Li

  DOI：10.1016/j.tet.2010.04.009

  日期：2010.6

  class of chiral eighteen-component three-dimensional supramolecular entities has been assembled in toluene and chloroform from twelve zinc porphyrin-appended 2-(ethylamino)- pyrimido[4,5-b][1,8]naphthyridin-4(3H)-one monomers and six chiral bipyridyl compounds. The heterocyclic segments form two C6-symmetric cyclic hexamers, which are stabilized by a well-established DDA–AAD hydrogen bonding motif, while

  从十二个卟啉锌加成的2-（乙基氨基）-嘧啶[4,5- b ] [1,8]萘啶-4（3 ）在甲苯和氯仿中组装了一类新的手性十八组分三维超分子实体H）一单体和六种手性联吡啶化合物。杂环链段形成两个C 6对称的环状六聚体，它们由成熟的DDA-AAD氢键基序稳定，而六个手性双吡啶配体与相应的卟啉锌单元配位，形成两层结构。该结构的特点是11 H NMR，UV-vis和圆二色性实验也表明，当单体的浓度足够高时，手性超分子实体可以排他地形成。
• Self-Assembly Mediated by the Donor−Donor−Acceptor·Acceptor−Acceptor−Donor (DDA·AAD) Hydrogen-Bonding Motif:  Formation of a Robust Hexameric Aggregate
  作者：Sergei V. Kolotuchin、Steven C. Zimmerman

  DOI：10.1021/ja981862r

  日期：1998.9.1