naproxen N,N-diisopropyl amide | 134780-13-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: naproxen N,N-diisopropyl amide
• 英文别名: (R)-N,N-diisopropyl-2-(6-methoxy-2-naphthyl)propionamide；(R)-naproxen N,N-diisopropyl amide；(2R)-2-(6-methoxynaphthalen-2-yl)-N,N-di(propan-2-yl)propanamide
• CAS: 134780-13-5
• 化学式: C₂₀H₂₇NO₂
• 分子量: 313.44
• InChiKey: PNEPTOHNOPKCIH-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  lithium;(Z)-1-[di(propan-2-yl)amino]-2-(6-methoxynaphthalen-2-yl)prop-1-en-1-olate 以90%的产率得到
  参考文献：
  名称：

  Vedejs E., Lee N., Sakata S. T., J. Amer. Chem. Soc., 116 (1994) N 5, S 2175-2176

  摘要：

  DOI：

文献信息

• Enantioselective Enolate Protonation with Chiral Anilines:  Scope, Structural Requirements, and Mechanistic Implications
  作者：E. Vedejs、A. W. Kruger、N. Lee、S. T. Sakata、M. Stec、E. Suna

  DOI：10.1021/ja994437m

  日期：2000.5.1

  substitution at the γ-carbon, γ-protonation can be a competing reaction in the case of the aliphatic substrates 12, 14b, 14d, and 18. The evidence is most consistent with a mechanism that involves proton transfer from 1a to a mixed aggregate consisting of enolate 4a and the lithiated amide 5, but direct proton transfer from 1a to the enolate is not ruled out.

  源自某些 β,γ 不饱和酸的 N,N-二异丙基酰胺（表 1，条目 1-4、7 和 10-13）的质子化已证明具有高对映选择性。根据双键几何结构和 γ-碳的取代度，在脂肪族底物 12、14b、14d 和 18 的情况下，γ-质子化可能是一种竞争反应。证据与涉及的机制最一致质子从 1a 转移到由烯醇化物 4a 和锂化酰胺 5 组成的混合聚集体，但不排除质子从 1a 直接转移到烯醇化物。
• Substituted Isoquinolines by Noyori Transfer Hydrogenation:  Enantioselective Synthesis of Chiral Diamines Containing an Aniline Subunit
  作者：E. Vedejs、P. Trapencieris、E. Suna

  DOI：10.1021/jo990594s

  日期：1999.9.1

  Transfer hydrogenation using the Noyori catalyst 5-Ts is effective for the enantioselective hydrogenation of imines containing fully substituted nitrogen groups (12 or 13). Analogues such as Ile could not be reduced in practical yield, apparently due to product inhibition of the catalyst. Asymmetric transfer hydrogenation of the aniline imine 8a was possible, but required. impractical purity levels for the substrate, and the nitro analogue 7 could not be reduced efficiently. The best results were Obtained with the bromophenyl imine 20, In the case of 20b, the product 21b was formed with 98.7% ee, and the material could be upgraded to >99% ee by crystallization of the hydrochloride salt. Reaction of 21b with NH3 or MeNH2 in the presence of Cu/CuCl gave the chiral anilines 10b or 23b. The latter substance is comparable to the commercially available 1 as a chiral proton donor fog amide enolates and provides access to the hitherto unavailable enantiomeric series.
• Enantioselective Enolate Protonation:  Matching Chiral Aniline and Substrate Acidity
  作者：E. Vedejs、A. W. Kruger、E. Suna

  DOI：10.1021/jo990897m

  日期：1999.10.1

  A comparison of chiral anilines 1a-f in the asymmetric protonation of enolate 15 shows that the optimum Delta pK(a) value (chiral acid vs protonated enolate) for the highest enantioselectivity is ca. 3 (Table 2). An extension of this concept to amino acid enolates was possible, and le was found to give the best enantioselectivity (85% ee) with the alanine-derived N-lithioenolate 5a (Table 3). Changes in aniline pK(a) due to variation of substituents at the aniline nitrogen were evaluated briefly, but these changes did not show consistent trends in the enantioselectivity vs pK(a).
• Lewis acid-induced internal proton return: enantiocontrolled protonation of an amide enolate
  作者：E. Vedejs、Namkyu Lee

  DOI：10.1021/ja00014a066

  日期：1991.7
• Catalytic Asymmetric Protonation of Amide Enolates:  Optimization of Kinetic Acidity in the Catalytic Cycle
  作者：Edwin Vedejs、Albert W. Kruger

  DOI：10.1021/jo972147n

  日期：1998.5.1