3-ethyl-4-methyl-5-p-toluenesulfonyl-3-pyrrolin-2-one | 184422-85-3

• 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-ethyl-4-methyl-5-p-toluenesulfonyl-3-pyrrolin-2-one
• 英文别名: 3-ethyl-1,5-dihydro-4-methyl-5-tosyl-2H-pyrrol-2-one；3-ethyl-4-methyl-5-tosyl-1,5-dihydro-2H-pyrrol-2-one；4-ethyl-3-methyl-2-(4-methylphenyl)sulfonyl-1,2-dihydropyrrol-5-one
• CAS: 184422-85-3
• 化学式: C₁₄H₁₇NO₃S
• 分子量: 279.36
• InChiKey: TUZDIQLDWRZBLU-UHFFFAOYSA-N

物化性质

• 沸点：
  538.5±50.0 °C(Predicted)
• 密度：
  1.206±0.06 g/cm3(Predicted)

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：

  3-ethyl-4-methyl-5-p-toluenesulfonyl-3-pyrrolin-2-one 在 sodium tetrahydroborate 作用下， 以76%的产率得到3-乙基-4-甲基-3-吡咯啉-2-酮
  参考文献：
  名称：

  Synthesis and properties of mesobilirubins XIIγ and XIIIγ and their mesobiliverdins

  摘要：

  The title pigments, with propionic acid groups displaced to the lactam end rings, were synthesized for the first time by the "1 + 2 + 1" approach, coupling two equivalents of a monopyrrole to a dipyrrylmethane (to give XII gamma), or the "2 + 2" approach, self-coupling two equivalents of a dipyrrinone (to give XIII gamma). Using the "1 + 2 + 1" approach, mesobilirubin III alpha was also prepared. Mesobilirubins XII gamma and XIII gamma are more polar than mesobilirubin III alpha and unlike III alpha cannot effectively engage the propionic acid groups in intramolecular hydrogen bonding to the dipyrrinone components. The new mesobilirubins give exciton coupled circular dichroism spectra in the presence of human serum albumin or quinine, with the XII gamma isomer exhibiting Cotton effect intensities nearly as strong as those from the III alpha isomer; whereas, the XIII gamma isomer exhibits far weaker intensities. Mesobilirubin III alpha requires glucuronidation for hepatobiliary elimination; whereas, XII gamma and XIII gamma do not, and they are excreted intact across the liver into bile. The corresponding biliverdins XII gamma and XIII gamma are reduced only slowly by biliverdin IX alpha reductase, in contrast to the fast reduction of the natural IX alpha isomer.

  DOI：

  10.1007/s00706-014-1160-6
• 作为产物：
  描述：

  2-(ethyloxycarbonyl)-3-ethyl-4-methylpyrrole 在 六甲基磷酰三胺 、 sodium hydroxide 、 N-碘代丁二酰亚胺 、 copper(l) iodide 、 碘 、 silver(I) acetate 、 碳酸氢钠 、 三氟乙酸 、 potassium iodide 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 3-ethyl-4-methyl-5-p-toluenesulfonyl-3-pyrrolin-2-one
  参考文献：
  名称：

  从 3,4-二取代 2-吡咯羧酸乙酯开始合成 3,4-二取代的 2-甲苯磺酰吡咯和 5-甲苯磺酰-1,5-二氢-2H-吡咯-2-酮

  摘要：

  3,4-二取代的 2-tosylpyrroles 和 5-tosyl-1,5-dihydro-2H-pyrrol-2-ones 的合成是通过 3,4-二取代的 2-iodo-5-tosylpyrroles 从乙基 3,4 开始的-二取代的 2-吡咯羧酸盐。

  DOI：

  10.1246/bcsj.69.3339

文献信息

• An Efficient Method to Construct the A,B-Rings Component toward Total Syntheses of Phycocyanobilin and Its Derivative as a Photoprobe
  作者：Krishanthi Padmarani Jayasundera、Hideki Kinoshita、Katsuhiko Inomata

  DOI：10.1246/bcsj.73.497

  日期：2000.2

  Total syntheses of phycocyanobilin and its derivative bearing a photoreactive group at the D-ring were accomplished by developing a new and efficient method for the construction of A,B-rings component, which consists of the Wittig-type new coupling reaction of 4-(1-methoxyethyl or 1-tosylethyl)-3-methyl-5-tosyl-1,5-dihydro-2H-pyrrol-2-one and a 2-formyl pyrrole derivative in the presence of nBu3P and a base, followed by reduction with aluminum amalgam and a subsequent acid or base treatment.

  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。
• Efficient Synthesis of B- and C-Rings Components of Phycobilin Derivatives for Structure/Function Analysis of Phytochrome
  作者：Atsuko Ohta、Daisuke Sawamoto、Krishanthi Padmarani Jayasundera、Hideki Kinoshita、Katsuhiko Inomata

  DOI：10.1246/cl.2000.492

  日期：2000.5

  B- and C-Rings components of phycobilin derivatives were efficiently prepared starting from the corresponding lactones. This synthetic method made it possible to prepare not only phycocyanobilin (PCB), but also PCB derivatives having butanoic acid side chain(s) instead of propanoic one(s), regioselectively monoesterified PCB derivatives at C8 or C12, and regioisomers of PCB with respect to methyl and propanoic acid substituents of B- and C-rings for the first time toward the structure/function analysis of phytochrome.

  从相应的内酯开始，高效地制备出了植物纤维素衍生物的 B 环和 C 环成分。这种合成方法不仅可以制备植物花青素（PCB），还可以制备具有丁酸侧链而非丙酸侧链的 PCB 衍生物、C8 或 C12 处的区域选择性单酯化 PCB 衍生物，以及 PCB 与 B 环和 C 环的甲基和丙酸取代基的区域异构体，从而首次实现了对植物色素的结构/功能分析。
• Total Syntheses of (±)-Phycocyanobilin and Its Derivatives Bearing a Photoreactive Group at D-ring
  作者：Takashi Kakiuchi、Hirohide Kato、Krishanthi Padmarani Jayasundera、Taijiro Higashi、Kazuhiko Watabe、Daisuke Sawamoto、Hideki Kinoshita、Katsuhiko Inomata

  DOI：10.1246/cl.1998.1001

  日期：1998.10

  (±)-Phycocyanobilin and its derivatives bearing a photoreactive group at D-ring were first synthesized by the development of a new and convenient method for the preparation of A-ring, transesterification for propanoic acid side-chains of the pyrrole derivative common to B- and C-rings, and deprotection of allyl ester side-chains with a palladium catalyst to avoid migration of exocyclic olefin of A-ring.

  (±)-藻蓝胆素及其在 D 环上带有光反应性基团的衍生物首先是通过开发一种新的方便的方法来合成的，该方法用于制备 A 环，对 B 共有的吡咯衍生物的丙酸侧链进行酯交换- 和 C 环，以及使用钯催化剂对烯丙酯侧链进行脱保护，以避免 A 环的环外烯烃迁移。
• Efficient Construction of A,B-Rings Component for Syntheses of Phycocyanobilin and Its Derivative
  作者：Krishanthi Padmarani Jayasundera、Hideki Kinoshita、Katsuhiko Inomata

  DOI：10.1246/cl.1998.1227

  日期：1998.12

  Total syntheses of phycocyanobilin and its photoactivatable derivative were accomplished by developing a new and versatile method for the construction of A,B-rings component, which consists of the Wittig-type new coupling reaction of 4-(1-methoxyethyl)-3-methyl-5-tosyl-1,5-dihydro-2H-pyrrol-2-one and a 2-formyl pyrrole derivative in the presence of nBu3P and a base, followed by reduction with aluminum amalgam and subsequent acid treatment.

  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。
• Syntheses of Biliverdin Derivatives Sterically Locked at the CD-Ring Components
  作者：Mostafa A. S. Hammam、Hiroshi Nakamura、Yukari Hirata、Htoi Khawn、Yasue Murata、Hideki Kinoshita、Katsuhiko Inomata

  DOI：10.1246/bcsj.79.1561

  日期：2006.10

  Total syntheses of biliverdin derivatives with a Z-syn, Z-anti, or E-syn CD-ring components were accomplished via new and efficient methods for the construction of sterically locked CD-ring components towards the elucidation of the stereochemistry of the chromophore in phytochromes.

  为了阐明植物色素中发色团的立体化学，我们采用新的高效方法构建了立体锁定的 CD 环成分，从而完成了具有 Z-syn、Z-anti 或 E-syn CD 环成分的胆绿素衍生物的全合成。