3-methyl-4-phenyl-3-pyrrolin-2-one | 10137-07-2

• 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-methyl-4-phenyl-3-pyrrolin-2-one
• 英文别名: 3-methyl-4-phenyl-1H-pyrrol-2(5H)-one；3-Methyl-4-phenyl-3-pyrrolin-2-on；4-Methyl-3-phenyl-1,2-dihydropyrrol-5-one；4-methyl-3-phenyl-1,2-dihydropyrrol-5-one
• CAS: 10137-07-2
• 化学式: C₁₁H₁₁NO
• 分子量: 173.214
• InChiKey: YKTLZEBAKGQAPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-methyl-4-phenyl-3-pyrrolin-2-one 在 甲醇 、 镍 作用下， 生成 (+/-)-cis-3-methyl-4-phenyl-pyrrolidin-2-one
  参考文献：
  名称：

  Heterocyclic Studies. IV. Evidence for the Structure of 2,3-Dihydro-5-methyl-6-phenyl-4H-1,2-diazepin-4-one¹

  摘要：

  DOI：

  10.1021/ja01531a044
• 作为产物：
  描述：

  1-(4-methylbenzensulfonyl)-4-phenyl-1H-1,2,3-triazole 在 dirhodium tetraacetate 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 1,2-二氯乙烷 、 苯 为溶剂， 生成 3-methyl-4-phenyl-3-pyrrolin-2-one
  参考文献：
  名称：

  铑催化的1-磺酰基-1,2,3-三唑与乙炔基甲硅烷基缩醛的铑催化合成3-吡咯啉-2-酮

  摘要：

  由1-磺酰基1,2,3-三唑生成的α-氨基铑类胡萝卜素与乙烯酮甲硅烷基缩醛应用于3 + 2环加成反应，提供了一种新颖而直接的合成方法，可合成具有广泛底物的生物学上令人感兴趣的化合物3-吡咯啉-2-酮范围。

  DOI：

  10.1021/ol501514b

文献信息

• Lewis base-catalyzed cyanation of Morita-Baylis-Hillman carbonates. Synthesis of allylamine derivatives
  作者：Hai Ma、Feng Sui、Qing-He Zhao、Ning Zhang、Yi Sun、Jing Xian、Meng-Jiao Jiao、Yu-ling Liu、Zhi-Min Wang

  DOI：10.1016/j.tetlet.2017.07.038

  日期：2017.8

  DABCO-catalyzed cyanation of MBH carbonates via 1,3-proton shift transfer is reported. The adducts of cyanation are converted in one step to allylic amines derivatives. The salient features of this reaction include readily available starting materials, mild conditions, broad substrate scope, high efficiency and valuable further applications. The process of the 1,3-proton shift transfer was conducted

  据报道，DABCO通过1，3-质子转移转移催化了MBH碳酸酯的氰化反应。一步将氰化加合物转化为烯丙基胺衍生物。该反应的显着特征包括容易获得的起始原料，温和的条件，广泛的底物范围，高效和有价值的进一步应用。1,3-质子转移转移的过程是通过NMR和DFT计算的联合研究进行的。
• Aromatic congeners of bilirubin: synthesis, stereochemistry, glucuronidation and hepatic transport
  作者：Justin O Brower、David A Lightner、Antony F McDonagh

  DOI：10.1016/s0040-4020(01)00773-6

  日期：2001.9

  A new synthetic analog (1) of the bile pigment bilirubin-IXα (bilirubin, Fig. 1) with phenyl groups replacing vinyl was prepared by a constitutional scrambling reaction of a mixture of two new, symmetric phenylrubin analogs (2 and 3) of bilirubin-XIIIα and IIIα. The former (2) with two endo-phenyls, and the latter (3) with two exo-phenyls were synthesized by condensation of a dipyrrylmethane dialdehyde

  通过将两个新的对称胆红素苯基胆红素类似物（2和3）的混合物进行结构加扰反应，制备了一个新的苯酚色素胆红素-IXα（胆红素，图1）的合成类似物（1），其中苯基取代了乙烯基。 -XIIIα和IIIα。前者（2）具有两个内切-phenyls，而后者（3）具有两个外-phenyls通过一个dipyrrylmethane二醛与适当methylphenylpyrrolinones，将其在几个步骤中制备的由4-甲基-3-苯基-2的缩合合成-（对甲苯磺酰基）吡咯，由Barton-Zard吡咯合成而得。核过载效应11 – 3的1 H NMR研究证实，与它们的胆红素当量一样，这些橙黄色颜料采用分子内氢键键合的脊-瓦构象。反相HPLC和TLC表明3的极性小于2，而1的极性中等。在的感应圆二色光谱差异大1 - 3中的人血清白蛋白的pH7.4的缓冲水溶液中发现。
• Synthesis, properties, and hepatic metabolism of strongly fluorescent fluorodipyrrinones
  作者：Stefan E. Boiadjiev、Zachary R. Woydziak、Antony F. McDonagh、David A. Lightner

  DOI：10.1016/j.tet.2006.04.046

  日期：2006.7

  From non-fluorescent 8-H fluorophenyldipyrrinones, highly fluorescent (phi(F) 0.4-0.6) analogs have been synthesized by reaction with 1,1'-carbonyidiimidazole to bridge the dipyrrinone nitrogens and form an NiN'-carbonyldipyrrinone (3H,5H-dipyrrolo[1,2-c:2',1'-f]-pyrimidine-3,5-dione). Amphiphilic, water-soluble 8-sulfonic acid derivatives are then obtained by reaction with coned H2SO4. The resulting fluorinated and sulfonated N,N'-carbonyl-bridged dipyrrinones, isolated as their sodium salts, are potential cholephilic fluorescence and F-19 MRI imaging agents for use in probing liver and biliary metabolism. After intravenous injection in the rat they were excreted rapidly and largely unchanged in bile. F-19 NMR spectroscopy of a pentafluorophenyl-tosylpyrrolinone synthetic precursor exhibited rarely seen diastereotopicity. (c) 2006 Elsevier Ltd. All rights reserved.