2-methoxy-2-(4-nitrophenyl)ethanol | 41959-09-5

• 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: 2-methoxy-2-(4-nitrophenyl)ethanol
• 英文别名: 2-methoxy-(p-nitrophenyl)ethanol；2-Methoxy-2-(p-nitrophenyl)-aethanol
• CAS: 41959-09-5
• 化学式: C₉H₁₁NO₄
• 分子量: 197.191
• InChiKey: LITBSQWRYUNWKR-UHFFFAOYSA-N

物化性质

• 沸点：
  340.9±32.0 °C(Predicted)
• 密度：
  1.270±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  75.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methoxy-2-(4-nitrophenyl)ethanol 在 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 生成 methoxy-(4-nitro-phenyl)-acetic acid
  参考文献：
  名称：

  构象对药物活性的影响。4.1-（对硝基苯基）-2-异丙基氨基乙醇的环状类似物。2-（对硝基苯基）-4-异丙基吗啉的肾上腺素β受体阻断活性的合成和评价。

  摘要：

  DOI：

  10.1021/jm00261a012
• 作为产物：
  描述：

  甲醇 、 (P-硝基苯基)环氧乙烷 在 三溴(丙-2-烯基)锡烷 作用下， 反应 24.0h， 以35%的产率得到2-methoxy-2-(4-nitrophenyl)ethanol
  参考文献：
  名称：

  烯丙基三溴化锡：一种多用途的试剂，涉及环氧化物的开环

  摘要：

  本文提出了一种用于环氧化物裂解的通用试剂。三溴化烯丙基锡可以作为一种新颖且易于制备的烯丙基化试剂和卤化物原子供体，分别在温和的反应条件下以高收率将环氧化物高产率地转化为相应的烯丙基醇和卤代醇。它也可以作为路易斯酸来催化环氧化物与醇的开环反应。

  DOI：

  10.1007/s11426-010-3200-3

文献信息

• Secondary deuterium isotope effects on epoxide methanolysis reactions
  作者：Robert P. Hanzlik、Richard B. Westkaemper

  DOI：10.1021/ja00527a060

  日期：1980.3

  tosylates and in the thermal cic-trans isomerization of cyclopropane derivatives. Another interesting result is the parallelism that the major reactions in acid and base both involve late or product-like transition states, while both minor reactions involve early or reactant-like transition states. These studies have shown that secondary deuterium isotope effects provide a sensitive and predictable probe

  二次动力学氘同位素效应最近被广泛用作反应机制和过渡态结构的探针。由于 CH 和 CD 键的面外弯曲能量不同，反应碳上的同位素取代会产生所谓的 ..cap alpha.. 效应；这些影响通常被解释为反应过程中反应碳上杂化的变化。或者，在与反应碳相邻的碳上进行同位素取代会导致 ..beta.. 效应，这可能是由于 CH 和 CD 带通过超共轭与反应碳上的轨道相互作用的能力不同而引起的。结合环氧化物-二醇途径的机理研究，二次氘同位素效应用于比较细胞色素 P-450 对烯烃的环氧化与间氯过苯甲酸对烯烃的环氧化。报道了二次氘同位素对 p-硝基苯乙烯氧化物的酸和碱催化甲醇分解作用的观察结果，这是一种环氧化物水合酶系统的化学模型系统。这是第一次观察到 ..cap alpha.. 效应在 ..beta.. 碳上或在相邻碳上的次要效应，不能归因于超共轭现象。这种效应可能是预期的，但在甲苯磺酸酯的溶剂分解和环丙烷衍生物的热
• Effects of para-substituents on the mechanisms of solvolysis of styrene oxides
  作者：Jeffrey J. Blumenstein、Victoria C. Ukachukwu、Ram S. Mohan、Dale L. Whalen

  DOI：10.1021/jo00056a027

  日期：1993.2

  Rate and product studies of the hydronium ion-catalyzed, hydroxide ion-catalyzed, and spontaneous reactions of styrene oxide and its p-CH3O-, p-CH3-, p-Cl-, and P-O2N-derivatives in water solutions have been carried out. A Hammett correlation of log k for the acid-catalyzed reactions vs sigma+ gives a slope rho+ of -4.2 and only diol products are formed. An intermediate in the hydronium ion-catalyzed hydrolysis of p-methoxystyrene oxide is trapped, subsequent to its rate-limiting formation, by azide ion. The spontaneous reactions of p-methylstyrene oxide and styrene oxide yield only diol products, and their reactions in 180-water indicate that greater-than-or-equal-to 98 % and ca. 95 %, respectively, of O-18 is incorporated into the benzyl positions. Nucleophilic addition of water to the benzyl carbon of neutral epoxide is proposed as the mechanism of the primary component of the spontaneous reaction for the p-CH3-, p-H- and p-Cl-substrates on the basis of a Hammett rho of -2.0. The spontaneous rate constant for reaction of p-methoxystyrene oxide is much greater than that expected from a Hammett correlation for the p-CH3-, p-H-, and p-Cl-styrene oxides. This increased rate is attributed to the incursion of a reaction that yields mainly (>80%) p-methoxyphenylacetaldehyde. The regiochemistries of addition of hydroxide ion in O-18-water to p-CH3-, p-H-, and p-Cl-substituted styrene oxides and addition of methoxide ion in methanol to p-CH3H, p-H-, p-Cl-, and P-O2N-substituted styrene oxides were also determined and found to vary as functions of the para substituent. Addition of hydroxide and methoxide ions to the a-carbon is favored by electron-donating groups in the phenyl ring, and addition of these nucleophiles to the beta-carbon is favored by electron-withdrawing groups in the phenyl ring.
• Carbon-13 and oxygen-18 kinetic isotope effects on methanolysis of p-nitrostyrene oxide
  作者：Stephen P. Jacober、Robert P. Hanzlik

  DOI：10.1021/ja00267a033

  日期：1986.4
• Wan, Peter; Muralidharan, S.; McAuley, Iain, Canadian Journal of Chemistry, 1987, vol. 65, p. 1775 - 1783
  作者：Wan, Peter、Muralidharan, S.、McAuley, Iain、Babbage, Christopher A.

  DOI：——

  日期：——
• WAN, PETER;MURALIDHARAN, S.;MCAULEY, IAIN;BABBAGE, CHRISTOPHER A., CAN. J. CHEM., 65,(1987) N 8, 1775-1783
  作者：WAN, PETER、MURALIDHARAN, S.、MCAULEY, IAIN、BABBAGE, CHRISTOPHER A.

  DOI：——

  日期：——