methyl (2S)-1-benzoyl-4-oxo-2-pyrrolidinecarboxylate | 169774-59-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2S)-1-benzoyl-4-oxo-2-pyrrolidinecarboxylate
• 英文别名: methyl (2S)-1-benzoyl-4-oxopyrrolidine-2-carboxylate；N-benzoyl-4-oxo-L-proline methyl ester；N-benzoyl-4-oxo-proline methyl ester；(2S)-N-Benzoyl-4-oxoproline methyl ester
• CAS: 169774-59-8
• 化学式: C₁₃H₁₃NO₄
• 分子量: 247.251
• InChiKey: HNVDCOMWAVDABV-NSHDSACASA-N

物化性质

• 沸点：
  414.2±45.0 °C(Predicted)
• 密度：
  1.295±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2S)-1-benzoyl-4-oxo-2-pyrrolidinecarboxylate 在 四(三苯基膦)钯 N,N-二甲基丙烯基脲 、 sodium carbonate 、 potassium carbonate 、 溶剂黄146 、 lithium chloride 、 lithium hexamethyldisilazane 作用下， 以 乙二醇二甲醚 、 水 、 苯 为溶剂， 反应 56.5h， 生成 (2S,3S)-N-benzoyl-2-methoxycarbonyl-3-tert-butoxycarbonylmethyl-4-(4-methoxyphenyl)-<4,5>-dehydropyrrolidine
  参考文献：
  名称：

  Towards a versatile synthesis of kainoids I: Introduction of the C-3 and C-4 substituents

  摘要：

  The first stages in the synthesis of acromelic acid analogues from trans-4-hydroxy-L-proline are described. An enamine alkylation was used to stereospecifically introduce the C-3 substituent, Grignard addition to a ketone or Pd(0) catalysed cross-coupling procedures adding C-4 aryl substituents for further manipulation. A number of versatile intermediates were generated. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00190-7
• 作为产物：
  描述：

  反式-4-羟基-L-脯氨酸甲酯盐酸盐 在 ruthenium trichloride 、 sodium periodate 、 碳酸氢钠 作用下， 以 四氢呋喃 、 四氯化碳 、 水 、 乙腈 为溶剂， 反应 8.0h， 生成 methyl (2S)-1-benzoyl-4-oxo-2-pyrrolidinecarboxylate
  参考文献：
  名称：

  Towards a versatile synthesis of kainoids I: Introduction of the C-3 and C-4 substituents

  摘要：

  The first stages in the synthesis of acromelic acid analogues from trans-4-hydroxy-L-proline are described. An enamine alkylation was used to stereospecifically introduce the C-3 substituent, Grignard addition to a ketone or Pd(0) catalysed cross-coupling procedures adding C-4 aryl substituents for further manipulation. A number of versatile intermediates were generated. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00190-7

文献信息

• Method for the preparation of N-substituted 4-ketoproline derivatives
  申请人：Degussa Aktiengesellschaft

  公开号：US05631385A1

  公开（公告）日：1997-05-20

  Method for the preparation of N-protected 4-ketoproline derivatives of formula I ##STR1## by oxidation of the corresponding N-protected 4-hydroxyproline derivatives of ##STR2## using the system TEMPO (2,2,6,6-tetramethylpiperidinyl oxy free radical)/NaOCl.

  通过使用TEMPO（2,2,6,6-四甲基哌啶氧自由基）/NaOCl体系，通过氧化相应的N-保护4-羟基脯氨酸衍生物，制备公式I的N-保护4-酮基脯氨酸衍生物的方法。
• Access to Optically Active 3-Azido- and 3-Aminopiperidine Derivatives by Enantioselective Ring Expansion of Prolinols
  作者：Anne Cochi、Domingo Gomez Pardo、Janine Cossy

  DOI：10.1021/ol201769b

  日期：2011.8.19

  The activation of N-alkyl prolinols by XtalFluor E allowed the formation of an aziridinium intermediate that can react with tetrabutylammonium azide (nBu4NN3) to produce 3-azidopiperidines and/or 2-(azidomethyl)pyrrolidines, in a ratio up to 100/0. These 3-azidopiperidines can be reduced to the corresponding 3-aminopiperidines.

  XtalFluor E活化N-烷基脯氨醇可形成叠氮基中间体，该叠氮基中间体可与叠氮化四丁基铵（n Bu 4 NN 3）反应生成3-叠氮基哌啶和/或2-（叠氮甲基）吡咯烷100/0。这些3-叠氮哌啶可以还原为相应的3-氨基哌啶。
• Diverted Total Synthesis of Promysalin Analogs Demonstrates That an Iron-Binding Motif Is Responsible for Its Narrow-Spectrum Antibacterial Activity
  作者：Andrew D. Steele、Colleen E. Keohane、Kyle W. Knouse、Sean E. Rossiter、Sierra J. Williams、William M. Wuest

  DOI：10.1021/jacs.6b03373

  日期：2016.5.11

  understand the mode of action of this natural product, we synthesized 16 analogs utilizing diverted total synthesis (DTS). Our analog studies revealed that the bioactivity of promysalin is sensitive to changes within its hydrogen bond network whereby alteration has drastic biological consequences. The DTS library not only yielded three analogs that retained potency but also provided insights that resulted in

  Promysalin 是一种具有独特生物活性的物种特异性假单胞菌代谢物。为了更好地了解这种天然产物的作用方式，我们利用转向全合成 (DTS) 合成了 16 种类似物。我们的模拟研究表明，promysalin 的生物活性对其氢键网络内的变化很敏感，由此改变会产生剧烈的生物学后果。DTS 文库不仅产生了三种保留效力的类似物，而且还提供了洞察力，导致鉴定了以前未知的 promysalin 结合铁的能力。这些发现与先前的观察结果相结合，暗示了天然产物在根际内具有复杂的多方面作用。
• Stereospecific Synthesis of (R)- and (S)-Baclofen and (R)- and (S)-PCPGABA (4-Amino-2-(4-chlorophenyl)butyric Acid) via (R)- and (S)-3-(4-Chlorophenyl)pyrrolidines.
  作者：Shigeyuki YOSHIFUJI、Mamoru KANAME

  DOI：10.1248/cpb.43.1302

  日期：——

  (R)- and (S)-Baclofen and (R)- and (S)-PCPGABA [4-amino-2-(4-chlorophenyl)butyric acid] were stereospecifically synthesized via (R)- and (S)-3-(4-chlorophenyl)pyrrolidines, starting from trans-4-hydroxy-L-proline. The syntheses involve two key operations, namely, 1) a stereoselective hydrogenation of dehydroproline derivatives controlled by the C-2 carboxyl function and 2) an effective ruthenium tetroxide oxidation to prepare chiral 3- and 4-(4-chlorophenyl)pyrrolidin-2-ones, which are dehydrated precursors of the target molecules.

  (R)-和(S)-巴克洛芬以及(R)-和(S)-PCPGABA [4-氨基-2-(4-氯苯基)丁酸] 是通过(R)-和(S)-3-(4-氯苯基)吡咯烷从反式-4-羟基-L-脯氨酸立体选择性合成的。合成过程包括两个关键操作，即：1) 由C-2羧基功能控制的脱氢脯氨酸衍生物的立体选择性氢化；2) 有效的四氧化铑氧化反应，以制备手性3-和4-(4-氯苯基)吡咯烷-2-酮，这些化合物是目标分子的脱水前体。
• [EN] NOVEL PROMYSALIN ANALOGUES AND METHODS OF USE THEREOF<br/>[FR] NOUVEAUX ANALOGUES DE PROMYSALINE ET PROCÉDÉS POUR LES UTILISER
  申请人：TEMPLE UNIVERSITY-OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCATION

  公开号：WO2017184558A1

  公开（公告）日：2017-10-26

  The present invention includes novel analogs of promysalin useful in preventing or treating a microbial infection. The present invention also includes methods preventing or treating a microbial infection in a subject in need thereof, the method comprising administering to the subject an effective amount of a compound of the invention.

  本发明包括新型的类似物质，可用于预防或治疗微生物感染。本发明还包括一种预防或治疗需要的受试者微生物感染的方法，该方法包括向受试者施用本发明化合物的有效量。