2,3-cis-3,4-trans-4-tert-butyl-2-hydroxy-3-phenyl-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester

• 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: 2,3-cis-3,4-trans-4-tert-butyl-2-hydroxy-3-phenyl-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2S,3R,4R)-4-tert-butyl-2-hydroxy-3-phenyl-3,4-dihydro-2H-quinoline-1-carboxylate
• 化学式: C₂₄H₃₁NO₃
• 分子量: 381.515
• InChiKey: SKXOYDMYULOVMV-HBMCJLEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(叔丁氧基羰基)-2-溴苯胺 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 水 、 正戊烷 为溶剂， 反应 21.42h， 生成 2,3-cis-3,4-trans-4-tert-butyl-2-hydroxy-3-phenyl-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Regioselective Carbolithiation of o-Amino-(E)-Stilbenes:  Cascade Route to the Quinoline Scaffold

  摘要：

  The regioselective carbolithiation of substituted ortho-amino-(E)-stilbenes can be exploited to initiate cascade reaction sequences that can be utilized as new routes to substituted 3,4-dihydro-1H-quinolin-2-ones,1,2,3,4-tetrahydroquinolines, 1,4-dihydroquinolines, and quinolines.

  DOI：

  10.1021/ol061348n

文献信息

• Carbolithiation of <i>o</i>-Amino-(<i>E</i>)-Stilbenes:  Diastereoselective Electrophile Substitution with Applications to Quinoline Synthesis
  作者：Anne-Marie L. Hogan、Donal F. O'Shea

  DOI：10.1021/jo7017679

  日期：2007.12.1

  [GRAPHICS]A regioselective carbolithiation of o-amino-(E)-stilbenes has been achieved with a series of alkyllithiums when THF is employed as the reaction solvent. The use of other solvents, such as diethyl ether or hydrocarbons, leads to a pronounced loss in regioselectivity. Moreover, high levels of diastereoselectivity have been obtained following reaction of the lithiated intermediate in THF with different electrophiles such as MeOD, CO2, and Bu3SnCl. It was shown that diastereoselectivity was influenced by the ortho-amino substituent and the alkyllithium utilized for carbolithiation with N-Boc substituent and t-BuLi proving optimal. In the case of carbolithiated intermediate 3a, obtained from the reaction of N-Boc substituted stilbene with t-BuLi, H-1 and C-13 NMR analysis revealed predominantly one diastereoisomer which was stable at room temperature. Application of the carbolithiation/electrophile reaction methodology to the synthesis of six-membered quinoline ring systems is demonstrated with substituted 3,4-dihydroquinolin-2-ones, 1,2,3,4-tetrahydroquinolines, 1,4-dihydroquinolines, and quinolines all prepared by a common cascade route.