<1,1,3,3-(2)H5>-4-hydroxy-4-(4'-nitrophenyl)butan-2-one | 155257-84-4

• 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: <1,1,3,3-(2)H5>-4-hydroxy-4-(4'-nitrophenyl)butan-2-one
• 英文别名: (4R,4S)-hydroxy-4-(4'-nitrophenyl)butan-2-one-1,1,1,3,3-d5；4-hydroxy-4-(4'-nitrophenyl)-(1,1,1,3,3-2H5)butan-2-one；1,1,1,3,3-pentadeuterio-4-hydroxy-4-(4-nitrophenyl)butan-2-one
• CAS: 155257-84-4
• 化学式: C₁₀H₁₁NO₄
• 分子量: 214.162
• InChiKey: DKESASVLMZGECV-YRYIGFSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.61
• 重原子数：
  15.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  80.44
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  <1,1,3,3-(2)H5>-4-hydroxy-4-(4'-nitrophenyl)butan-2-one 在 五氯化磷 、 水 作用下， 以 乙醚 为溶剂， 生成 <1,1,3,3-(2)H5>-4-chloro-4-(4'-nitrophenyl)butan-2-one
  参考文献：
  名称：

  Mechanisms of elimination and substitution reactions. Spontaneous solvolysis reactions via carbanion and carbocation intermediates

  摘要：

  The reactions of 4-(4'-nitrophenyl)-4-X-butan-2-one (1-X; X = Cl, OTs) with added bases/nucleophiles exhibit second-order kinetics. These substitution and elimination reactions are concluded to be of concerted S(N)2 type and irreversible E1cB type, respectively. The spontaneous formation of alkene from the chloride L-CI is suggested to occur by a water-promoted E1cB reaction. The fraction of elimination product is smaller with the tosylate 1-OTs. It is plausible that the elimination and substitution reactions of 1-OTs are carbocation reactions since the Bronsted plot with substituted acetate anion bases shows a tenfold positive deviation for the 'water-catalyzed' elimination reaction, and there is a trace of substitution reaction with the acetonitrile component of the solvent yielding 1-NHCOMe. These results are consistent with a common, very short-lived, carbocation intermediate. Copyright (C) 1999 John Wiley & Sons, Ltd.

  DOI：

  10.1002/(sici)1099-1395(199902)12:2<116::aid-poc102>3.0.co;2-8
• 作为产物：
  描述：

  氘代丙酮 、 对硝基苯甲醛 生成 <1,1,3,3-(2)H5>-4-hydroxy-4-(4'-nitrophenyl)butan-2-one
  参考文献：
  名称：

  Mechanisms of elimination and substitution reactions. Spontaneous solvolysis reactions via carbanion and carbocation intermediates

  摘要：

  The reactions of 4-(4'-nitrophenyl)-4-X-butan-2-one (1-X; X = Cl, OTs) with added bases/nucleophiles exhibit second-order kinetics. These substitution and elimination reactions are concluded to be of concerted S(N)2 type and irreversible E1cB type, respectively. The spontaneous formation of alkene from the chloride L-CI is suggested to occur by a water-promoted E1cB reaction. The fraction of elimination product is smaller with the tosylate 1-OTs. It is plausible that the elimination and substitution reactions of 1-OTs are carbocation reactions since the Bronsted plot with substituted acetate anion bases shows a tenfold positive deviation for the 'water-catalyzed' elimination reaction, and there is a trace of substitution reaction with the acetonitrile component of the solvent yielding 1-NHCOMe. These results are consistent with a common, very short-lived, carbocation intermediate. Copyright (C) 1999 John Wiley & Sons, Ltd.

  DOI：

  10.1002/(sici)1099-1395(199902)12:2<116::aid-poc102>3.0.co;2-8

文献信息

• The Mechanism of Base-Promoted HF Elimination from 4-Fluoro-4-(4-nitrophenyl)butan-2-one Is E1cB. Evidence from Double Isotopic Fractionation Experiments
  作者：Per Ryberg、Olle Matsson

  DOI：10.1021/jo010773l

  日期：2002.2.1

  Leaving-group fluorine and secondary deuterium multiple kinetic isotope effects (KIEs) have been determined for the base-promoted HF elimination from the 4-fluoro-4-(4'-nitrophenyl)-(1,1,1,3,3-(2)H(5))butan-2-one. The fluorine KIE was determined by using the accelerator-produced short-lived radionuclide (18)F in combination with the naturally abundant (19)F. The (19)F substrate was labeled with (14)C

  已确定了从4-氟-4-（4'-硝基苯基）-（1,1,1,3,3-）碱促进的HF消除的离去氟和次级氘多重动力学同位素效应（KIE） （2）H（5））丁-2-。通过使用促进剂生产的短寿命放射性核素（18）F与天然富集的（19）F的组合来确定氟KIE。（19）F底物在远处用（14）​​C标记，以能够测量两种底物的放射性。当使用乙酸盐作为碱时，测定的氟KIE的尺寸为1.0009 +/- 0.0010。甲酸，乙酸盐和咪唑的次级氘KIE分别为1.009 +/- 0.017、1.000 +/- 0.018和1.010 +/- 0.023。与我们最近报道的质子底物的相应KIE相比，这些KIE的大小明显较小。
• Shokat; Uno; Schultz, Journal of the American Chemical Society, 1994, vol. 116, # 6, p. 2261 - 2270
  作者：Shokat、Uno、Schultz

  DOI：——

  日期：——