3-(4,5-Methylenedioxy-2-nitrophenyl)propanoic acid | 180589-04-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 3-(4,5-Methylenedioxy-2-nitrophenyl)propanoic acid
• 英文别名: 3-(6-nitro-benzo[1,3]dioxol-5-yl)-propionic acid；3-(6-Nitro-benzo[1,3]dioxol-5-yl)-propionsaeure；3-(6-Nitro-1,3-benzodioxol-5-yl)propanoic acid
• CAS: 180589-04-2
• 化学式: C₁₀H₉NO₆
• 分子量: 239.185
• InChiKey: UIWBKWAQFQOIBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(4,5-Methylenedioxy-2-nitrophenyl)propanoic acid 在 吡啶 、 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 3-(6-nitrobenzo[d][1,3]dioxol-5-yl)-N-phenylpropanamide
  参考文献：
  名称：

  New orally effective 3-(2-nitro)phenylpropanamide analgesic derivatives: Synthesis and antinociceptive evaluation

  摘要：

  A series of substituted 6-nitrophenylpropanamide derivatives (1-20) were synthesized using either the TDAE strategy or classical organic reactions. All these compounds were characterized by fusion point, 1H NMR,13C NMR, elemental analysis or mass spectrometry data. Because of their structural analogy with recently published compounds possessing antinociceptive properties, our derivatives were screened for peripheral analgesic activities on acetic acid-induced writhing in mice. Compound 13 showed the best result at 100 junol/kg ip (50% inhibition vs 59% for aspirin). This antinociceptive activity was maintained after oral administration (40% inhibition vs 31.6% for aspirin). Both hot-plate and actimetry-based tests were non-significant suggesting the analgesic activity of 13 linked to a peripheral mechanism. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.041
• 作为产物：
  描述：

  3-[3,4-(亚甲二氧基)苯基]丙酸 在 硝酸 作用下， 以 溶剂黄146 为溶剂， 反应 3.0h， 生成 3-(4,5-Methylenedioxy-2-nitrophenyl)propanoic acid
  参考文献：
  名称：

  Novel 1,3,4-thiadiazolium-2-phenylamine chlorides derived from natural piperine as trypanocidal agents: Chemical and biological studies

  摘要：

  We herein describe the synthesis and characterization of nine new 1,3,4-thiadiazolium-2-phenylamine chlorides derived from natural piperine. We evaluate their toxic effects against the different evolutive forms of Trypanosoma cruzi, and the host cell (murine macrophages). The results obtained show that mesoionic hydrochloride MI possesses the best activity profile. Compound MI may be a prototype for use in the development of a new chemotherapeutic agent with high efficiency, which may be employed in the treatment of Chagas' disease. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.12.049

文献信息

• Condensation of Carboxylic Acids with Non-Nucleophilic <i>N</i>-Heterocycles and Anilides Using Boc₂O
  作者：Atsushi Umehara、Hirofumi Ueda、Hidetoshi Tokuyama

  DOI：10.1021/acs.joc.6b02097

  日期：2016.11.18

  A novel condensation reaction of carboxylic acids with various non-nucleophilic N-heterocycles and anilides was developed. The reaction proceeds in the presence of di-tert-butyl dicarbonate (Boc2O), catalytic 4-(dimethylamino)pyridine (DMAP), and 2,6-lutidine and is applicable to the acylation of a wide range of non-nucleophilic nitrogen compounds, including indoles, pyrroles, pyrazole, carbazole,

  开发了一种新型的羧酸与各种非亲核N-杂环和苯甲酸酯的缩合反应。在二-的存在下该反应进行叔丁基酯（BOC 2 O），催化4-（二甲氨基）吡啶（DMAP），和2,6-二甲基吡啶，并适用于范围广泛的非亲核的酰化具有高官能团相容性的氮化合物，包括吲哚，吡咯，吡唑，咔唑，内酰胺，恶唑烷酮和苯甲酸酯。还研究了吲哚，羧酸和苯胺的范围。
• A Search for Quantitative Acylation of α-Trinositol (1<scp>d</scp>-<i>myo</i>-Inositol 1,2,6-<i>tris</i>(dihydrogen phosphate) Pentasodium Salt)
  作者：Mats Malmberg、Nicola Rehnberg

  DOI：10.1080/07328309608005666

  日期：1996.5

  The acylation of alpha-trinositol is very sensitive to reaction conditions. Competing condensation reactions may give pyrophosphates and cyclic phosphates. Treatment of a tert-ammonium salt corresponding to alpha-trinositol with carboxylic acid anhydride and DMAP gives a good yield of the expected esters.
• Narang et al., Journal of the Indian Chemical Society, 1936, vol. 13, p. 260,262
  作者：Narang et al.

  DOI：——

  日期：——
• Baker; Robinson, Journal of the Chemical Society, 1925, vol. 127, p. 1433
  作者：Baker、Robinson

  DOI：——

  日期：——
• Synthesis of an Acyloxymethyl Prodrug of the Inositol Phosphate α-Trinositol
  作者：Anneli Lindahl、Mats Malmberg、Nicola Rehnberg

  DOI：10.1080/07328309608005673

  日期：1996.7

  Acyloxymethylation of an acylated silver salt of alpha-trinositol gives, after deprotection, membrane permeable 1D-myo-inositol 1,2,6-tris(ethoxycarbonyloxymethyl sodium phosphate). The acyl groups, 3-(4,5-methylenedioxy-2-nitrophenyl)propanoyl are cleaved by hydrogenolysis.