3,4,5-trimethoxybenzoic acid 2,5-dioxo-1-pyrrolidinyl ester | 69705-20-0

• 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: 3,4,5-trimethoxybenzoic acid 2,5-dioxo-1-pyrrolidinyl ester
• 英文别名: Cambridge id 5274185；(2,5-dioxopyrrolidin-1-yl) 3,4,5-trimethoxybenzoate
• CAS: 69705-20-0
• 化学式: C₁₄H₁₅NO₇
• 分子量: 309.276
• InChiKey: FKVDOCZMBDDTLH-UHFFFAOYSA-N

物化性质

• 沸点：
  463.9±55.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  91.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3,4,5-trimethoxybenzoic acid 2,5-dioxo-1-pyrrolidinyl ester 、 乙二胺 以 四氢呋喃 为溶剂， 反应 15.0h， 以1.47 g的产率得到2-(3,4,5-trimethoxybenzoyl)aminoethylamine
  参考文献：
  名称：

  Cyclodextrin-Isolated Alkynylpyrenes as UV-Stable and Blue-Light-Emitting Molecules Even in Condensed States

  摘要：

  Encapsulation of highly emissive alkynylpyrenes with permethylated alpha-cyclodextrin (PM-alpha-CD) followed by capping reaction yielded alkynylpyrene-based [3]rotaxanes. The [3]rotaxane emitted only blue light of monomeric pyrene under various circumstances such as lipophilic, hydrophilic, and even condensed states and exhibited extremely high stability for UV irradiation. These properties would result because PM-alpha-CD, like bulletproof glass, protected the alkynylpyrene core from the attack of another excited alkynylpyrene and singlet oxygen generated by the energy transfer from the excited alkynylpyrene.

  DOI：

  10.1021/acs.orglett.6b00420
• 作为产物：
  描述：

  丁二酰亚胺三氟乙酸酯 、 3,4,5-三甲氧基苯甲酸 在 吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以80%的产率得到3,4,5-trimethoxybenzoic acid 2,5-dioxo-1-pyrrolidinyl ester
  参考文献：
  名称：

  Synthesis, Crystal Structure and Anti-Fatigue Effects of Some Benzamide Derivatives

  摘要：

  一系列苯甲酰胺衍生物，如1-(1,3-苯并二氧六环-5-基羰基)哌啶(1-BCP)，通过一种新方法，利用取代的苯甲酸与哌啶、吗啉或吡咯烷反应合成。这些苯甲酰胺衍生物的晶体通过重结晶获得。目标化合物和中间体的结构通过FT-IR、1H-NMR和元素分析以及选择性样品的X射线晶体学确定。这些化合物的晶体结构有望用于识别α-氨基-3-羟基-5-甲基异恶唑-4-丙酸(AMPA)受体的变构调节剂的结合位点。研究了苯甲酰胺衍生物在负重强迫游泳小鼠中的抗疲劳作用，以游泳耐力测试作为疲劳的指标。b3、d3和e3组的力竭游泳时间比咖啡因组更长(p < 0.05)。总之，b3、d3和e3增强了小鼠的强迫游泳能力。抗疲劳作用的机制将在未来进行研究。

  DOI：

  10.3390/molecules19011034

文献信息

• New antiarrhythmic agents. 2,2,5,5-Tetramethyl-3-pyrroline-3-carboxamides and 2,2,5,5-tetramethylpyrrolidine-3-carboxamides.
  作者：Olga H. Hankovsky、Kalman Hideg、Ilona Bodi、Laszlo Frank

  DOI：10.1021/jm00157a005

  日期：1986.7

  by forming the Schiff bases and subsequent sodium borohydride reduction. Other tetramethyl-3-pyrrolinecarboxamide compounds were synthesized by acylating the aminoalkyl compounds with 2,2,6,6-tetramethyl-3,5-dibromo-4-piperidinone in a reaction involving Favorskii rearrangement. Saturation of the double bond of some pyrroline derivatives furnished the pyrrolidinecarboxamides. The new compounds of each

  N-（ω-氨基烷基）-2,2,5,5-四甲基-3-吡咯啉或-吡咯烷-3-羧酰胺通过反应性酸衍生物（酰氯，活化的酯，邻苯二甲酸酐，邻苯二甲酰亚胺，2-烷基-4H-3,1-苯并恶嗪-4-酮）或通过形成席夫碱和随后的硼氢化钠还原将它们烷基化。通过在涉及Favorskii重排的反应中将氨基烷基化合物与2,2,6,6-四甲基-3,5-二溴-4-哌啶酮酰化来合成其他四甲基-3-吡咯啉羧酰胺化合物。一些吡咯啉衍生物的双键的饱和提供了吡咯烷甲酰胺。每种类型的新化合物对乌头碱引起的心律失常均具有活性，其中一些具有比奎尼丁更高的活性和更好的化疗指数。从每种类型的活性新化合物中选出的一些实例显示出对哇巴因引起的心律不齐具有强活性。为了进行比较，选择了已知的药物，如利多卡因，美西律和托卡尼特。最有效的化合物被氧化为顺磁性氮氧化物，后者被还原为N-羟基衍生物。这些产品没有或仅有减少的抗心律失常作用。
• Decarboxylative Amidation of Aryl/Heteroarylacetic Acids via Activated Esters through Traceless α-Functionalized Benzylic Radicals
  作者：Joydev K. Laha、Upma Gulati、Anjali Gupta

  DOI：10.1021/acs.orglett.3c00927

  日期：2023.5.19

  amide synthesis, a decarboxylative amidation of aryl/heteroarylacetic acids by reaction with NHS and tert-butyl nitrite has been reported to afford both aliphatic and (hetero)aromatic amides in satisfactory yields. Mechanistic studies revealed a previously unexplored pathway for the formation of an activated ester through the generation and subsequent reactions of traceless α-functionalized benzylic

  与传统的酰胺合成不同，据报道，芳基/杂芳基乙酸通过与 NHS 和亚硝酸叔丁酯反应进行脱羧酰胺化，以令人满意的收率提供脂肪族和（杂）芳族酰胺。机理研究揭示了一种以前未探索过的活化酯形成途径，即通过无痕α-官能化苄基自由基的产生和随后的反应，随后与胺进行单锅反应形成酰胺。Moclobemide 的克级合成表明其实际适用性。
• Synthesis, Crystal Structure and Anti-Fatigue Effects of Some Benzamide Derivatives
  作者：Xianglong Wu、Wutu Fan、Yalei Pan、Yuankun Zhai、Yinbo Niu、Chenrui Li、Qibing Mei

  DOI：10.3390/molecules19011034

  日期：——

  A series of benzamide derivatives such as 1-(1,3-benzodioxol-5-ylcarbonyl) piperidine (1-BCP) were synthesized by the reaction of substituted benzoic acids with piperidine, morpholine or pyrrolidine using a novel method. The crystals of these benzamide derivatives were obtained by recrystallization. Structures of target and intermediate compounds were determined via FT-IR, 1H-NMR and elemental analysis and X-ray crystallography of select examples. The crystal structures of these compounds have potential applications to identify the binding site for allosteric modulators of the α-amino-3-hydroxy-5-methylisoxazole-4-propionic acid (AMPA) receptor. The anti-fatigue effects of the benzamide derivatives in weight-loaded forced swimming mice were investigated in a swimming endurance capacity test used as an indicator of fatigue. The swimming times to exhaustion were longer in the b3, d3, and e3 groups than in the caffeine group (p < 0.05). In conclusion, b3, d3 and e3 enhanced the forced swimming capacity of mice. The mechanism of the anti-fatigue effects will be studied in the future.

  一系列苯甲酰胺衍生物，如1-(1,3-苯并二氧六环-5-基羰基)哌啶(1-BCP)，通过一种新方法，利用取代的苯甲酸与哌啶、吗啉或吡咯烷反应合成。这些苯甲酰胺衍生物的晶体通过重结晶获得。目标化合物和中间体的结构通过FT-IR、1H-NMR和元素分析以及选择性样品的X射线晶体学确定。这些化合物的晶体结构有望用于识别α-氨基-3-羟基-5-甲基异恶唑-4-丙酸(AMPA)受体的变构调节剂的结合位点。研究了苯甲酰胺衍生物在负重强迫游泳小鼠中的抗疲劳作用，以游泳耐力测试作为疲劳的指标。b3、d3和e3组的力竭游泳时间比咖啡因组更长(p < 0.05)。总之，b3、d3和e3增强了小鼠的强迫游泳能力。抗疲劳作用的机制将在未来进行研究。
• Cyclodextrin-Isolated Alkynylpyrenes as UV-Stable and Blue-Light-Emitting Molecules Even in Condensed States
  作者：Masahiko Inouye、Atsushi Yoshizawa、Mari Shibata、Yuki Yonenaga、Kazuhisa Fujimoto、Takuma Sakata、Shinya Matsumoto、Motoo Shiro

  DOI：10.1021/acs.orglett.6b00420

  日期：2016.5.6

  Encapsulation of highly emissive alkynylpyrenes with permethylated alpha-cyclodextrin (PM-alpha-CD) followed by capping reaction yielded alkynylpyrene-based [3]rotaxanes. The [3]rotaxane emitted only blue light of monomeric pyrene under various circumstances such as lipophilic, hydrophilic, and even condensed states and exhibited extremely high stability for UV irradiation. These properties would result because PM-alpha-CD, like bulletproof glass, protected the alkynylpyrene core from the attack of another excited alkynylpyrene and singlet oxygen generated by the energy transfer from the excited alkynylpyrene.