7-{[3,5-Bis-(3,5-di-tert-butyl-benzyloxy)-benzyl]-tert-butoxycarbonyl-amino}-2-chloro-[1,8]naphthyridine-3-carboxylic acid ethyl ester | 213680-86-5

• 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: 7-{[3,5-Bis-(3,5-di-tert-butyl-benzyloxy)-benzyl]-tert-butoxycarbonyl-amino}-2-chloro-[1,8]naphthyridine-3-carboxylic acid ethyl ester
• 英文别名: Ethyl 7-[[3,5-bis[(3,5-ditert-butylphenyl)methoxy]phenyl]methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]-2-chloro-1,8-naphthyridine-3-carboxylate
• CAS: 213680-86-5
• 化学式: C₅₃H₆₈ClN₃O₆
• 分子量: 878.592
• InChiKey: UEQCOKXWSNBAIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.8
• 重原子数：
  63
• 可旋转键数：
  18
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  7-{[3,5-Bis-(3,5-di-tert-butyl-benzyloxy)-benzyl]-tert-butoxycarbonyl-amino}-2-chloro-[1,8]naphthyridine-3-carboxylic acid ethyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以86%的产率得到7-[3,5-Bis-(3,5-di-tert-butyl-benzyloxy)-benzylamino]-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
• 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 、 18-冠醚-6 、 乙醇 、 potassium carbonate 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 59.0h， 生成 7-{[3,5-Bis-(3,5-di-tert-butyl-benzyloxy)-benzyl]-tert-butoxycarbonyl-amino}-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

• 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