N,N-diisopropyl-2-phenylbutanamide | 94430-02-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N-diisopropyl-2-phenylbutanamide
• 英文别名: N,N-diisopropyl-2-phenylbutyramide；α-Ethyl-phenylessigsaeure-diisopropylamid；2-phenyl-N,N-di(propan-2-yl)butanamide
• CAS: 94430-02-1
• 化学式: C₁₆H₂₅NO
• 分子量: 247.381
• InChiKey: SZRQPHRFSSRMAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N-diisopropyl-2-phenylbutanamide 在 N-fluorobis<(trifluoromethyl)sulfonyl>imide 、 lithium diisopropyl amide 作用下， 生成 N,N-diisopropyl-2-fluoro-2-phenylbutyramide
  参考文献：
  名称：

  N-fluorobis[(trifluoromethyl)sulfonyl]imide: an efficient reagent for the .alpha.-fluorination of functionalized carbonyl compounds

  摘要：

  The N-fluorobis[(trifluoromethyl)sulfonyl]imide (1) has been used in the electrophilic fluorination of the lithium enolate of esters, amides, and ketones. The corresponding alpha-fluorocarbonyl compounds have been obtained in good yields. The alpha-fluorination of beta-diesters, beta-diamides, beta-keto esters, and beta-diketones has been performed either on the neutral compounds or on the metal enolates. In this way some geminal azafluoro, chlorofluoro, fluorooxy compounds have been prepared in nearly quantitative yields. Also some alpha-keto esters and acids have been selectively monofluorinated in the beta-position by simple treatment of the neutral compound with 1.

  DOI：

  10.1021/jo00016a022
• 作为产物：
  描述：

  二异丙胺 在 水 、 cesium fluoride 氯化镍二甲氧基乙烷 、 左旋去甲麻黄碱 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 N,N-二甲基乙酰胺 为溶剂， 反应 17.0h， 生成 N,N-diisopropyl-2-phenylbutanamide
  参考文献：
  名称：

  镍/去氧麻黄碱络合物催化的活化和未活化仲烷基卤的Hiyama反应。

  摘要：

  DOI：

  10.1002/anie.200700440

文献信息

• The synthesis and characterisation of deuteriated amides
  作者：Gregory S. Coumbarides、Jason Eames、Stephanos Ghilagaber

  DOI：10.1002/jlcr.737

  日期：2003.10.15

  Results are reported on the regioselective C-deuteriation of a series of enolates derived from the addition of sec-BuLi to a variety of substituted amides. The outcomes of the reactions are discussed in terms of the structural nature of the amides and the deuteriated sources employed. Copyright © 2003 John Wiley & Sons, Ltd.

  报告了对一系列烯醇类化合物进行区域选择性 C 去氘化的结果，这些烯醇类化合物是通过仲丁基锂与各种取代酰胺的加成反应得到的。根据酰胺的结构性质和所采用的去氘代来源，对反应的结果进行了讨论。Copyright © 2003 John Wiley & Sons, Ltd. All Rights Reserved.
• 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。
• Hiyama Reactions of Activated and Unactivated Secondary Alkyl Halides Catalyzed by a Nickel/Norephedrine Complex
  作者：Neil A. Strotman、Stefan Sommer、Gregory C. Fu

  DOI：10.1002/anie.200700440

  日期：2007.5.4
• N-fluorobis[(trifluoromethyl)sulfonyl]imide: an efficient reagent for the .alpha.-fluorination of functionalized carbonyl compounds
  作者：Giuseppe Resnati、Darryl D. DesMarteau

  DOI：10.1021/jo00016a022

  日期：1991.8

  The N-fluorobis[(trifluoromethyl)sulfonyl]imide (1) has been used in the electrophilic fluorination of the lithium enolate of esters, amides, and ketones. The corresponding alpha-fluorocarbonyl compounds have been obtained in good yields. The alpha-fluorination of beta-diesters, beta-diamides, beta-keto esters, and beta-diketones has been performed either on the neutral compounds or on the metal enolates. In this way some geminal azafluoro, chlorofluoro, fluorooxy compounds have been prepared in nearly quantitative yields. Also some alpha-keto esters and acids have been selectively monofluorinated in the beta-position by simple treatment of the neutral compound with 1.