5-甲酰基-3-甲基-1H-吡咯-2,4-二羧酸二乙酯 | 2199-60-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 5-甲酰基-3-甲基-1H-吡咯-2,4-二羧酸二乙酯
• 中文别名: 4-甲基-3,5-二乙氧羰基-2-甲酰基吡咯
• 英文名称: diethyl 5-formyl-3-methylpyrrole-2,4-dicarboxylate
• 英文别名: diethyl 5-formyl-3-methyl-1H-pyrrole-2,4-dicarboxylate；2-Formyl-4-methyl-3,5-diethoxycarbonylpyrrol；3,5-Diethoxycarbonyl-2-formyl-4-methyl-pyrrol
• CAS: 2199-60-2
• 化学式: C₁₂H₁₅NO₅
• mdl: MFCD00030389
• 分子量: 253.255
• InChiKey: WPKKEQCPXUTCDZ-UHFFFAOYSA-N

物化性质

• 熔点：
  125 °C
• 沸点：
  439.7±45.0 °C(Predicted)
• 密度：
  1.238±0.06 g/cm3(Predicted)
• 溶解度：
  20.7 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  85.5
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  5-甲酰基-3-甲基-1H-吡咯-2,4-二羧酸二乙酯 在 3-苄基羟乙基甲基噻唑氯化锂 、 对甲苯磺酸 sodium acetate 、 三乙胺 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 4.0h， 生成 diethyl 4-methyl-2-(2-methyl-1-phenyl-5-pyrrolyl)pyrrole-3,5-dicarboxylate
  参考文献：
  名称：

  吡咯研究。：第36部分1 2,2'-联吡咯及其相关化合物的合成

  摘要：

  与噻唑鎓盐反应生成的2-甲酰基吡咯的酰基阴离子当量，对but-1-en-3-one进行亲核加成，生成1-（2-吡咯基）pent-1,4-二酮，并经Paal-与氨和伯胺的克诺尔反应，得到2,2'-联吡咯。或者，可以通过2-叠氮基-5-（2-吡咯基）戊-2，4-二烯酸酯的热解获得2，2′-联吡咯系统。

  DOI：

  10.1016/s0040-4020(01)87527-x
• 作为产物：
  描述：

  2,4-二甲基吡咯-3,5-二羧酸二乙酯 在 ammonium cerium(IV) nitrate 作用下， 以 四氢呋喃 、 水 、 溶剂黄146 为溶剂， 反应 1.0h， 以86%的产率得到5-甲酰基-3-甲基-1H-吡咯-2,4-二羧酸二乙酯
  参考文献：
  名称：

  硝酸铈铵将吡咯α-甲基氧化为甲酰基

  摘要：

  当吡咯环也具有α-羧酸酯基时，可以通过用硝酸铈铵氧化吡咯α-甲基来高产率地制备吡咯α-醛。

  DOI：

  10.1016/0040-4039(95)00790-j

文献信息

• Electron-withdrawing group effect in aryl group of allyl bromides for the successful synthesis of indolizines via a novel [3+3] annulation approach
  作者：Sujin Park、Ikyon Kim

  DOI：10.1016/j.tet.2015.02.013

  日期：2015.4

  A new synthetic approach to 6,7-disubstituted indolizines has been developed from pyrrole-2-carboxaldehydes and allyl bromides via two successive base-mediated reactions. As three-carbon units for formation of pyridine moiety of indolizines, allyl bromides easily derived from Morita–Baylis–Hillman (MBH) adducts were employed. We found that positioning electron-withdrawing group(s) at the aromatic ring

  通过两个连续的碱介导的反应，由吡咯-2-羧醛和烯丙基溴开发了一种新的合成方法来合成6,7-二取代的吲哚嗪。作为形成吲哚嗪吡啶部分的三碳单元，采用了容易从森田-贝利斯-希尔曼（MBH）加合物衍生的烯丙基溴。我们发现，在烯丙基溴的芳香环上放置吸电子基团是成功闭环的关键，以允许获得具有独特取代方式的吲哚嗪。同样通过该方法组装结构上相关的咪唑并[1,2- a ]吡啶和吡啶并[1,2- a ]吲哚。
• Domino Knoevenagel Condensation/Intramolecular Aldol Cyclization Route to Diverse Indolizines with Densely Functionalized Pyridine Units
  作者：Myungock Kim、Youngeun Jung、Ikyon Kim

  DOI：10.1021/jo401801j

  日期：2013.10.18

  A highly efficient [4 + 2] annulation route to polysubstituted indolizines is described employing a domino Knoevenagel condensation/intramolecular aldol cyclization process as a key step. Construction of pyridine rings in indolizine skeleton was rapidly achieved from several pyrrole-2-carboxaldehydes in good to excellent yields, leading to indolizines with various substituents at the 5, 6, and 7 positions

  描述了采用多米诺Knoevenagel缩合/分子内羟醛环化过程作为关键步骤的高效[4 + 2]环合成多取代吲哚嗪的方法。吲哚嗪骨架中吡啶环的构建可以快速地以良好至极佳的产率由几种吡咯-2-羧醛实现，这导致吲哚嗪类在5、6和7位具有各种取代基，具体取决于反应的活性亚甲基配偶体。
• 인돌리진 유도체, 이의 약학적으로 허용 가능한 염, 이의 제조방법 및 이를 유효성분으로 포함하는 약학적 조성물
  申请人：UIF (University Industry Foundation), Yonsei University 연세대학교 산학협력단(220050095099) BRN ▼110-82-10500

  公开号：KR101558475B1

  公开（公告）日：2015-10-07

  본 발명은 인돌리진 유도체, 이의 약학적으로 허용 가능한 염, 이의 제조방법 및 이를 유효성분으로 포함하는 골 질환 또는 암의 예방 또는 치료용 약학적 조성물에 관한 것이다. 본 발명의 인돌리진 유도체는 파골세포의 분화를 억제하여 골다공증과 같은 파골세포 관련 골 질환에 대한 치료 효과를 나타내며, 암세포의 사멸을 유도하여 항암 활성을 나타내므로, 골 질환과 암에 대한 예방 및 치료제로서 유용하게 이용될 수 있다.

  本发明涉及吲哚啉衍生物，其药学上可接受的盐，其制备方法以及包含其作为有效成分的用于预防或治疗骨疾病或癌症的药学组合物。该吲哚啉衍生物抑制成骨细胞的分化，表现出对与成骨细胞相关的骨疾病如骨质疏松症的治疗效果，并诱导癌细胞凋亡，表现出抗癌活性，因此可作为预防和治疗骨疾病和癌症的药物。
• Solvothermal Synthesis of Multiple Dihydropyrimidinones at a Time as Inhibitors of Eg5
  作者：Xiao-Qiang Jiang、Shi-Quan Chen、Yan-Fei Liu、Xin-Guang Pan、Dan Chen、Shi-Fan Wang

  DOI：10.3390/molecules26071925

  日期：——

  Solvothermal synthesis of multiple dihydropyrimidinones at a time has been developed in inexpensive and green bio-based solvent lactic acid without any additional catalysts or additives. By this method, thirty new dihydropyrimidinone derivatives were synthesized in two batches and characterized. All of the compounds were screened by Eg5 motor protein ATPase assay, and the positive compounds were tested against the Caco-2 cell line, HeLa cell line, L929 cell line and T24 cell line in vitro. Among them, compound C9 exhibited the best inhibitory activity against motor protein ATPase with an IC50 value of 30.25 μM and significant cytotoxic activity in the micromolar range against the cells above. The Lineweaver–Burk plot revealed that compound C9 was a mixed-type Eg5 inhibitor. A molecular modeling study using the Discovery Studio program was performed, where compound C9 exhibited good binding interaction with Eg5 motor protein ATPase, and this was consistent with the attained experimental results.

  在廉价且绿色的生物基溶剂乳酸中，已经开发出一种同时合成多个二氢嘧啶酮的溶剂热合成方法，无需任何额外的催化剂或添加剂。通过这种方法，已经合成并表征了30种新的二氢嘧啶酮衍生物。所有化合物均通过Eg5马达蛋白ATP酶活性分析进行筛选，并对阳性化合物进行了体外针对Caco-2细胞系、HeLa细胞系、L929细胞系和T24细胞系的测试。其中，化合物C9对马达蛋白ATP酶表现出最佳的抑制活性，IC50值为30.25 μM，并在微摩尔范围内对上述细胞表现出显著的细胞毒性活性。Lineweaver–Burk图表明，化合物C9是一种混合型Eg5抑制剂。使用Discovery Studio程序进行的分子建模研究显示，化合物C9与Eg5马达蛋白ATP酶有良好的结合相互作用，与实验结果一致。
• Readily Synthesized Novel Fluorescent Dipyrrinones
  作者：Stefan E. Boiadjiev、David A. Lightner

  DOI：10.1021/jo040183y

  日期：2005.1.1

  A new, highly fluorescent (φF up to 0.85) rigid anti-Z-dipyrrinone chromophore has been synthesized in high yield in a one-pot reaction by condensing two monopyrroles in the presence of DBU to form the pyrrolo[3,2-f]indolizine-4,6-dione nucleus.

  一个新的，高荧光（φ ˚F高达0.85）刚性抗- ž -dipyrrinone发色团已经在一个单釜反应高收率由在DBU存在缩合两种monopyrroles以形成吡咯合成[3,2- ˚F ] indolizine-4,6-dione核。