4-ethyl-3-methyl-5-(p-toluenesulfonyl)-1,5-dihydro-1H-pyrrolin-2-one | 152796-98-0

• 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: 4-ethyl-3-methyl-5-(p-toluenesulfonyl)-1,5-dihydro-1H-pyrrolin-2-one
• 英文别名: 4-ethyl-1,5-dihydro-3-methyl-5-tosyl-2H-pyrrol-2-one；4-ethyl-3-methyl-5-tosyl-1,5-dihydro-2H-pyrrol-2-one；5-tosyl-4-ethyl-3-methyl-pyrrolin-2-one；3-Ethyl-4-methyl-2-(4-methylphenyl)sulfonyl-1,2-dihydropyrrol-5-one
• CAS: 152796-98-0
• 化学式: C₁₄H₁₇NO₃S
• 分子量: 279.36
• InChiKey: WDPNZBXQVCLOST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-ethyl-3-methyl-5-(p-toluenesulfonyl)-1,5-dihydro-1H-pyrrolin-2-one 在 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 乙腈 、 苯 为溶剂， 反应 49.0h， 生成 4-(1-bromoethyl)-1-t-butoxycarbonyl-1,5-dihydro-3-methyl-5-tosyl-2H-pyrrol-2-one
  参考文献：
  名称：

  Efficient Construction of A,B-Rings Component for Syntheses of Phycocyanobilin and Its Derivative

  摘要：

  该方法包括 4-(1-甲氧基乙基)-3-甲基-5-对甲苯磺酰基-1,5-二氢-2H-吡咯-2-酮和 2-甲酰基吡咯衍生物在 nBu3P 和碱存在下的 Wittig 型新偶联反应，然后用铝汞齐还原并进行酸处理。

  DOI：

  10.1246/cl.1998.1227
• 作为产物：
  描述：

  tert-Butyl-(3-ethyl-4-methyl-pyrrolyl-2)-methanoat 在 N-碘代丁二酰亚胺 、 三氟化硼乙醚 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 97.0h， 生成 4-ethyl-3-methyl-5-(p-toluenesulfonyl)-1,5-dihydro-1H-pyrrolin-2-one
  参考文献：
  名称：

  An Efficient Method to Construct the A,B-Rings Component toward Total Syntheses of Phycocyanobilin and Its Derivative as a Photoprobe

  摘要：

  通过开发一种新颖且高效的方法构建A、B环部分，成功完成了藻蓝蛋白胆色素及其在D环上具有光反应基团的衍生物的总合成。该方法包括在nBu3P和碱存在下，4-(1-甲氧基乙基或1-托烯乙基)-3-甲基-5-托烯-1,5-二氢-2H-吡咯烷-2-酮与2-呋喃基吡咯衍生物的Wittig型新偶联反应，随后用铝齐聚物还原，并进行酸或碱处理。

  DOI：

  10.1246/bcsj.73.497

文献信息

• Convenient and Regioselective Syntheses of 3,4-Disubstituted Δ³-Pyrrolin-2-one Derivatives Starting from 2-Tosyl-3,4-Disubstituted Pyrroles
  作者：Hideki Kinoshita、Yoshio Hayashi、Yasue Murata、Katsuhiko Inomata

  DOI：10.1246/cl.1993.1437

  日期：1993.8

  3,4-Disubstituted Δ3-pyrrolin-2-ones were prepared in high yields via 5-tosyl-Δ3-pyrrolin-2-ones (4) starting from 2-tosylpyrroles regioselectively. The compounds 4 were found to be useful intermediates for the preparation of a variety of Δ3-pyrrolin-2-one derivatives. The reactions of 4 with various nucleophiles and active methylene compounds bearing an appropriate leaving group are described.

  通过 5-tosyl-Δ3-pyrrolin-2-ones (4) 从 2-tosylpyrroles 开始区域选择性地制备 3,4-二取代的 Δ3-pyrrolin-2-ones。发现化合物4是用于制备多种Δ3-吡咯啉-2-酮衍生物的有用中间体。描述了 4 与各种亲核试剂和带有适当离去基团的活性亚甲基化合物的反应。
• An improved coupling procedure for the barton-zard pyrrole synthesis
  作者：Pavel Bobál、David A. Lightner

  DOI：10.1002/jhet.5570380239

  日期：2001.3

  final step in the Barton-Zard pyrrole synthesis uses inexpensive potassium carbonate as base in the coupling-cyclization reaction of vic-nitro-acetates with isocyanides. In this modification the isolated yields of synthetically useful 2-carboalkoxypyrroles (1a,b and 3) and 2-(p-toluenesulfonyl)pyrroles (2a,b) consistently rise to the 78-89% range. Conversion of 2a to 5-(p-toluenesulfonyl)-2-pyrrolinone

  Barton-Zard吡咯合成中改进的最终步骤在vic-硝基乙酸酯与异氰酸酯的偶联环化反应中使用廉价的碳酸钾作为碱。在该修饰中，合成上有用的2-羰基烷氧基吡咯（1a，b和3）和2-（对甲苯磺酰基）吡咯（2a，b）的分离产率始终提高到78-89％的范围。通过与30％的过氧化氢在乙酸中反应，可方便而直接地将2a转化为5-（对甲苯磺酰基）-2-吡咯烷酮4，从而避免了涉及溴化然后溶剂分解的两步程序。
• Total Syntheses of Phycocyanobilin Derivatives Bearing a Modified A-Ring toward the Structure/Function Analysis of Phytochrome
  作者：Daisuke Sawamoto、Hiroshi Nakamura、Hideki Kinoshita、Shuhei Fujinami、Katsuhiko Inomata

  DOI：10.1246/cl.2000.1398

  日期：2000.12

  Phycocyanobilin (PCB) derivatives bearing a modified A-ring, including 3,3′-dihydrogenated PCB derivatives, were efficiently synthesized in free acid forms by applying our original methods for the preparation of A-, A/B-, and C/D-ring components toward the structure/function analysis of phytochrome.

  为了对植物色素进行结构/功能分析，我们采用独创的 A-环、A/B-环和 C/D 环成分制备方法，高效合成了具有修饰 A 环的植物花青素（PCB）衍生物，包括 3,3′-二氢化 PCB 衍生物的游离酸形式。
• Novel Linear Tetrapyrroles: Hydrogen Bonding in Diacetylenic Bilirubins
  作者：Bin Tu、Brahmananda Ghosh、David A. Lightner

  DOI：10.1007/s00706-003-0157-3

  日期：2004.5.1

  Bilirubin congeners with dipyrrinones conjoined to a diaceteylene unit (-Cequivalent toC-Cequivalent toC-) rather than to -CH2- were synthesized and examined spectroscopically. This new class of rubrified linear tetrapyrroles cannot easily fold or bend in the middle, but the dipyrrinones can rotate independently about the diacetylene unit. Thus, unlike bilirubin, which is bent in the middle and has a ridge-tile shape, the diacetylene unit orients the attached dipyrrinones along a linear path, and intramolecular hydrogen bonding between the dipyrrinones and opposing carboxylic acids preserves a twisted linear molecular shape when the usual propionic acids are replaced by hexanoic. In a bis-hexanoic acid rubin, the extended planes of the dipyrrinones intersect along the -(Cequivalent toC)(2)- axis at an angle of 102degrees for the conformation stabilized by intramolecular hydrogen bonding. With propionic acid chains, however, neither CO2H can engage an opposing dipyrrinone in intramolecular hydrogen bonding, and the energy-minimum conformation of this linear pigment, shows nearly co-planar dipyrrinones, with an intersection of an angle of similar to180degrees of the extended planes of the dipyrrinones. Spectroscopic evidence for such linearized and twisted (bis-hexanoic) and planar (bis-propionic) structures comes from the pigments' NMR spectral data and their exciton UV-Vis and induced circular dichroism spectra.
• Stable 4E-dipyrrinones
  作者：Stefan E. Boiadjiev、David A. Lightner

  DOI：10.1016/s0040-4020(99)00617-1

  日期：1999.9

  Dipyrrinones formed by DBU and n-Bu3P-promoted condensation of 5-p-toluene-sulfonylpyrrolinones with pyrrole 2-aldehydes, gave high yields of product with predominantly the E-configuration when the aldehyde had a 5-carboethoxy group. The 4E-dipyrrinones were readily purified by chromatography and were stable in solutions shielded from light. (C) 1999 Elsevier Science Ltd. All rights reserved.