2,4,7-trimethyl-1,8-naphthyridine | 14757-44-9

• 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: 2,4,7-trimethyl-1,8-naphthyridine
• CAS: 14757-44-9
• 化学式: C₁₁H₁₂N₂
• 分子量: 172.23
• InChiKey: WJJNPDSYYWZSBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,4,7-trimethyl-1,8-naphthyridine 在 正丁基锂 、 重水 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 2,7-Bis(deuteriomethyl)-4-methyl-1,8-naphthyridine
  参考文献：
  名称：

  Regioselective Addition ofn-Alkyllithiums to α,α′-Disubstituted-1,8-Naphthyridines: Synthesis of 6-Amino-3-Pyridinol Analogs of α-Tocopherol

  摘要：

  在非极性溶剂（如 Et2O-己烷混合物）中，将正烷基锂加入到δ,δ′-二取代的-1,8-萘啶中。在极性溶剂（如四氢呋喃）中，烷基锂充当碱而不是亲核体。对于能够与（烷基）锂试剂进行五元环螯合的底物，可实现区域选择性加成。以 TBS 保护醇作为共螯合基团的底物具有最佳的产率和区域选择性。这种方法被成功用于制备五甲基色醇（PMC）的两种 6-氨基-3-吡啶醇类似物，PMC 是一种δ-生育酚衍生物，其异戊烯侧链被截断为一个甲基。

  DOI：

  10.1055/s-2005-865308

文献信息

• BIOMOLECULE BINDING LIGANDS
  申请人：Lowe Christopher Robin

  公开号：US20100203650A1

  公开（公告）日：2010-08-12

  The invention provides biomolecule binding ligands, collections of biomolecule binding ligands, and their use in the purification of biological mixtures and in the identification of ligands having an affinity for a substance. The ligand is a compound of formula (III) or a compound of formula (IV): wherein for compounds of formula (I) one of R 1a , R 1b , R 2 , R 3 and R 4 is a group comprising a linker attached to a support, and the others of R 1a , R 1b , R 2 , R 3 and R 4 are independently selected from optionally substituted C 1-20 alkyl, optionally substituted C 3-20 heterocyclyl or optionally substituted C 5-20 aryl, and R 1a , R 1b and R 2 are additionally selected from hydrogen, and R 2 is additionally further selected from —S(═O)R 5 and —C(═S)NR 6 R 7 , wherein R 5 , R 6 and R 7 are independently optionally substituted C 1-20 alkyl, optionally substituted C 3-20 heterocyclyl or optionally substituted C 5-20 aryl, or, optionally, two or more of the others of R 1a , R 1b , R 2 , R 3 and R 4 , together with the atoms to which they are bound, may form a ring; and for compounds of formula (II) one of R 1a , R 1b , R 3 and R 4 is a group comprising a linker attached to a support, and the others of R 1a , R 1b , R 3 and R 4 are independently selected optionally substituted C 1-20 alkyl, optionally substituted C 3-20 heterocyclyl or optionally substituted C 5-20 aryl, and R 1a , and R 1b are additionally selected from hydrogen, or, optionally, two or more of the others of R 1a , R 1b , R 3 and R 4 , together with the atoms to which they are bound, may form a ring.
• [EN] BIOMOLECULE BINDING LIGANDS<br/>[FR] LIGANDS SE LIANT À DES BIOMOLÉCULES
  申请人：CAMBRIDGE ENTPR LTD

  公开号：WO2009007676A2

  公开（公告）日：2009-01-15

  The invention provides biomolecule binding ligands, collections of biomolecule binding ligands, and their use in the purification of biological mixtures and in the identification of ligands having an affinity for a substance. The ligand is a compound of formula (III) or a compound of formula (IV): wherein for compounds of formula (I) one of R1a, R1b,R2, R3 and R4 is a group comprising a linker attached to a support, and the others of R1a, R1b,R2, R3 and R4 are independently selected from optionally substituted C1-20 alkyl, optionally substituted C3-20 heterocyclyl or optionally substituted C5-20 aryl, and R1a, R1b and R2 are additionally selected from hydrogen, and R2 is additionally further selected from -S(=O)R5 and -C(=S)NR6R7, wherein R5, R6 and R7 are independently optionally substituted C1-20 alkyl, optionally substituted C3-20 heterocyclyl or optionally substituted C5-20 aryl, or, optionally, two or more of the others of R1a, R1b,R2, R3 and R4, together with the atoms to which they are bound, may form a ring; and for compounds of formula (II) one of R1a, R1b, R3 and R4 is a group comprising a linker attached to a support, and the others of R1a, R1b, R3 and R4 are independently selected optionally substituted C1-20 alkyl, optionally substituted C3-20 heterocyclyl or optionally substituted C5-20 aryl, and R1a, and R1b are additionally selected from hydrogen, or, optionally, two or more of the others of R1a, R1b, R3 and R4, together with the atoms to which they are bound, may form a ring.
• Regioselective Addition of<i>n</i>-Alkyllithiums to α,α′-Disubstituted-1,8-Naphthyridines: Synthesis of 6-Amino-3-Pyridinol Analogs of α-Tocopherol
  作者：Derek A. Pratt、Ned A. Porter、Tae-gyu Nam、Maikel Wijtmans

  DOI：10.1055/s-2005-865308

  日期：——

  n-Alkyllithiums were added to α,α′-disubstituted-1,8-naphthyridines in non-polar solvents such as Et2O-hexane mixtures. In polar solvents such as THF, alkyllithium acts as a base rather than a nucleophile. Regioselective addition was achieved for substrates capable of five-membered cyclic chelation of the (alkyl)lithium reagent. Substrates with a TBS-protected alcohol as the co-chelating moiety afforded the best combination of yield and regioselectivity. This methodology was successfully employed in the preparation of two 6-amino-3-pyridinol analogs of pentamethylchromanol (PMC), an α-tocopherol derivative with its isoprenoid side chain truncated to a methyl group.

  在非极性溶剂（如 Et2O-己烷混合物）中，将正烷基锂加入到δ,δ′-二取代的-1,8-萘啶中。在极性溶剂（如四氢呋喃）中，烷基锂充当碱而不是亲核体。对于能够与（烷基）锂试剂进行五元环螯合的底物，可实现区域选择性加成。以 TBS 保护醇作为共螯合基团的底物具有最佳的产率和区域选择性。这种方法被成功用于制备五甲基色醇（PMC）的两种 6-氨基-3-吡啶醇类似物，PMC 是一种δ-生育酚衍生物，其异戊烯侧链被截断为一个甲基。

表征谱图