2-nitrobenzoic acid 1-hexyl ester | 117375-30-1

• 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: 2-nitrobenzoic acid 1-hexyl ester
• 英文别名: n-hexyl 2-nitrobenzoate；hexyl 2-nitrobenzoate；2-nitro-benzoic acid hexyl ester；2-Nitro-benzoesaeure-hexylester
• CAS: 117375-30-1
• 化学式: C₁₃H₁₇NO₄
• 分子量: 251.282
• InChiKey: ROFHAYXXTGCRHO-UHFFFAOYSA-N

物化性质

• 沸点：
  344.3±15.0 °C(Predicted)
• 密度：
  1.133±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-nitrobenzoic acid 1-hexyl ester 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 2-[2-(2-nitrobenzoylamino)-4-methoxycarbonylbenzoylamino]benzoic acid 1-hexyl ester
  参考文献：
  名称：

  Oligoanthranilamides. Non-Peptide Subunits That Show Formation of Specific Secondary Structure

  摘要：

  A family of novel oligomers based on the anthranilamide nucleus has been prepared and shown to form well-defined secondary structural features. H-1 NMR and X-ray crystallographic techniques have demonstrated that intramolecular hydrogen bonds play a key role in stabilizing both linear sheet and helical conformational forms.

  DOI：

  10.1021/ja9539857
• 作为产物：
  描述：

  己基叠氮化物 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 2-nitrobenzoic acid 1-hexyl ester
  参考文献：
  名称：

  己基三氮杂丁二烯作为有效的烷基化剂

  摘要：

  烷基重氮离子是合成化学家武器库中最具反应性的烷基化剂。就是说，很少有方法可以选择性和安全地利用这种化学方法。本文中，我们显示了使用稳定的己基三氮杂丁二烯作为反应性重氮离子的来源，该反应性重氮离子经过弱亲核试剂（如羧酸盐，甚至磺酸盐）的取代化学反应。在不存在亲核试剂的情况下，观察到发生消除。为了克服源于该反应副产物抑制的问题，我们显示了三氮杂丁二烯可以用异氰酸甲苯磺酰基预活化。

  DOI：

  10.1016/j.tetlet.2017.05.056

文献信息

• Epoxide as precatalyst for metal-free catalytic transesterification
  作者：Shinji Tanaka、Takuya Nakashima、Naoto Satou、Hiromi Oono、Yoshihiro Kon、Masanori Tamura、Kazuhiko Sato

  DOI：10.1016/j.tetlet.2019.06.056

  日期：2019.7

  Transesterification of methyl esters was accelerated by an in situ-generated metal-free catalyst comprising a quaternary alkylammonium salt and an epoxide. The combination of a quaternary alkylammonium acetate and glycidol is optimal, and various esters were synthesized from methyl esters with alcohols in good to excellent yield. Analysis of the catalyst solution revealed that basic species are generated

  通过原位生成的包含季烷基铵盐和环氧化物的无金属催化剂促进了甲酯的酯交换反应。乙酸季烷基铵和缩水甘油的组合是最佳的，并且由甲基酯与醇合成各种酯，收率良好至极佳。催化剂溶液的分析表明，碱性物质是由环氧化物的开环反应产生的。
• Steric Effects in Acid-Catalyzed Decomposition and Base-Catalyzed Cyclization of 1-(2-Alkoxycarbonylphenyl)-3-phenyltriazenes
  作者：Oldřich Pytela、Aleš Halama

  DOI：10.1135/cccc19960751

  日期：——

  Eight derivatives of 1-(2-alkoxycarbonylphenyl)-3-phenyltriazene (R = methyl, ethyl, propyl, isopropyl, butyl, isobutyl, hexyl, and allyl) have been synthesized and their UV-VIS, IR, ¹H and ¹³C NMR spectra measured. The NMR spectra have been interpreted in detail. The kinetics of acid-catalyzed decomposition and base-catalyzed cyclization of the title compounds have been measured in 52.1% w/w methanol at 25.0 °C. The unit reaction order has been verified and the cyclization product has been identified. The pH-profiles obtained have been used to calculate the catalytic rate constants k_A (acid-catalyzed decomposition) and k_B (base-catalyzed cyclization) of all the derivatives; the constants have been interpreted with regard to inductive and steric effects. The catalytic rate constant k_A has been found to be independent of the substituents. The catalytic rate constant k_B depends statistically significantly upon both inductive and steric effects, the sensitivity to the former being more significant. The experimental results and their interpretation confirm the base-catalyzed cyclization mechanism with formation of tetrahedral intermediate as the rate-limiting step.

  已合成了1-(2-烷氧羰基苯基)-3-苯基三氮烯的八种衍生物（R = 甲基、乙基、丙基、异丙基、丁基、异丁基、己基和烯丙基），并测量了它们的紫外-可见、红外、^1H和^13C核磁共振光谱。详细解释了核磁共振光谱。在25.0°C的52.1% w/w甲醇中测定了这些化合物的酸催化分解和碱催化环化的动力学。验证了单位反应阶数，并鉴定了环化产物。利用得到的pH-曲线计算了所有衍生物的酸催化分解催化速率常数kA和碱催化环化催化速率常数kB；这些常数已根据归纳和空间效应进行了解释。发现酸催化分解催化速率常数kA与取代基无关。碱催化环化催化速率常数kB在统计上显著取决于归纳和空间效应，对前者的敏感性更显著。实验结果及其解释证实了碱催化环化机制，形成四面体中间体作为速率限制步骤。
• ZHANG, JINGWEN;XU, ZHILUO;HUANG, HUAMIN;CENG, WEI, ACTA SCI. NATUR. UNIV. JILINENSIS,(1988) N 1, 112-114
  作者：ZHANG, JINGWEN、XU, ZHILUO、HUANG, HUAMIN、CENG, WEI

  DOI：——

  日期：——