4-(tert-butoxy)-2-methylquinoline | 1040365-70-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-(tert-butoxy)-2-methylquinoline
• 英文别名: 2-Methyl-4-[(2-methylpropan-2-yl)oxy]quinoline；2-methyl-4-[(2-methylpropan-2-yl)oxy]quinoline
• CAS: 1040365-70-5
• 化学式: C₁₄H₁₇NO
• 分子量: 215.295
• InChiKey: QDSGNPKQLRGTPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-氯喹哪啶 、 sodium t-butanolate 在 tris(dibenzylideneacetone)dipalladium (0) 2-Ph-C₆H₄-P-tBu₂ 作用下， 以 甲苯 、 叔丁醇 为溶剂， 反应 0.03h， 以65%的产率得到4-(tert-butoxy)-2-methylquinoline
  参考文献：
  名称：

  Palladium-mediated C–N, C–C, and C–O functionalization of azolopyrimidines: a new total synthesis of variolin B

  摘要：

  A new total synthesis of the alkaloid variolin B is achieved by a selective and sequential palladium-mediated functionalization of a trihalo-substituted pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine. This intermediate is obtained by a new heterocyclization reaction between an appropriate bromomethyl azaindole and N-tosylmethyl dichloroformimide. The methodology may be effective for the synthesis of some analogs by substitution on the relatively unexplored C4 and C9 positions of the alkaloid. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.04.063

文献信息

• Comparative Screening of DalPhos/Ni Catalysts in C‐N Cross‐couplings of (Hetero)aryl Chlorides Enables Development of Aminopyrazole Cross‐couplings with Amine Base
  作者：Nicole Martinek、Kathleen M. Morrison、Justin M. Field、Samuel A. Fisher、Mark Stradiotto

  DOI：10.1002/chem.202203394

  日期：2023.2

  nucleophiles, electrophiles, solvents, and bases enabled the development of the first metal-catalyzed C−N cross-couplings of aminopyrazoles and related heteroatom-dense nucleophiles with (hetero)aryl chlorides using an amine ‘dual-base’ system.

  对镍催化的 C−N 交叉偶联中 DalPhos 配体家族的竞争性评估涉及一组不同的测试亲核试剂、亲电试剂、溶剂和碱，从而能够开发第一个金属催化的氨基吡唑和使用胺“双碱基”系统与（杂）芳基氯相关的杂原子致密亲核试剂。
• Palladium-mediated C–N, C–C, and C–O functionalization of azolopyrimidines: a new total synthesis of variolin B
  作者：Alejandro Baeza、Javier Mendiola、Carolina Burgos、Julio Alvarez-Builla、Juan J. Vaquero

  DOI：10.1016/j.tetlet.2008.04.063

  日期：2008.6

  A new total synthesis of the alkaloid variolin B is achieved by a selective and sequential palladium-mediated functionalization of a trihalo-substituted pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine. This intermediate is obtained by a new heterocyclization reaction between an appropriate bromomethyl azaindole and N-tosylmethyl dichloroformimide. The methodology may be effective for the synthesis of some analogs by substitution on the relatively unexplored C4 and C9 positions of the alkaloid. (C) 2008 Elsevier Ltd. All rights reserved.