1,2,3-三甲氧基-5-(硝基甲基)苯 | 512797-31-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1,2,3-三甲氧基-5-(硝基甲基)苯
• 英文名称: 1,2,3-trimethoxy-5-(nitromethyl)benzene
• CAS: 512797-31-8
• 化学式: C₁₀H₁₃NO₅
• 分子量: 227.217
• InChiKey: HXNVJOMWNSCARA-UHFFFAOYSA-N

物化性质

• 沸点：
  335.9±37.0 °C(Predicted)
• 密度：
  1.192±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  73.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,4,5-三甲氧基甲苯 在 硝酸 、 溶剂黄146 作用下， 反应 1.5h， 以35%的产率得到1,2,3-三甲氧基-5-(硝基甲基)苯
  参考文献：
  名称：

  A Switchable Oxidation Process Leading to Two Various Versatile Pharmaceutical Intermediates

  摘要：

  An efficient high-yielding and environmentally benign switchable oxidation process that can selectively produce two different versatile synthetic intermediates is disclosed. One of the two intermediates, 2,3-dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (coenzyme Q(0)), is obtained by menu of a telescoped two-step synthetic protocol that in the first step involves treatment of the substrate (1,2,3-trimethoxy-5-methylbenzene) with hydrogen peroxide in acetic acid with p-toluene sulphonic acid present as a Bronsted acid catalyst, succeeded by a telescoped second step that entails treatment with fuming nitric acid to achieve the target molecule in an excellent isolated yield (88%). If the substrate is treated directly with nitric acid (659) in glacial acetic acid two different products can be obtained, namely acetic acid 3,4,5-trimethoxybenzyl ester in a superb isolated yield (93%) or, under slightly altered reaction conditions, 1,2,3-trimethoxy-5-(nitromethyl)benzene in a moderate to low yield (35%) and low selectivity. The two pathways leading to the two different products in the nitric acid oxidation protocol were investigated by means of DFT calculations as an aid to elaborate a proposal for the reaction mechanism.

  DOI：

  10.1021/op100185x

文献信息

• Preparation of Ring-Methoxylated Arylnitromethanes by the Victor Meyer Reaction
  作者：Victor P. Kislyi、Anna S. Maksimenko、Petr A. Buikin、Elena D. Daeva、Victor V. Semenov

  DOI：10.1055/s-0041-1737534

  日期：2022.6

  arylnitromethanes and nitrite esters. A modified approach for the isolation of arylnitromethanes is described, which represents a valuable improvement of the established Victor Meyer reaction. The isolation technique, which involves reaction of the nitrite ester with urea in methanol, allows the desired arylnitromethanes to be isolated, without loss, in 29–75% yields, and generates the corresponding recyclable

  易于获得且稳定的环甲氧基化苄基氯与 AgNO2 反应生成相应的芳基硝基甲烷和亚硝酸酯的混合物。描述了一种改进的芳基硝基甲烷分离方法，它代表了对已建立的 Victor Meyer 反应的有价值的改进。该分离技术涉及亚硝酸酯与脲在甲醇中的反应，可以以 29-75% 的收率无损失地分离出所需的芳基硝基甲烷，并生成相应的可回收苯甲醇。出乎意料的是，环甲氧基化苄基碘不能使用，因为它们不够稳定并且在开发的反应条件下会产生焦油。