(S)-methyl 2-(N-allyl-2-nitrophenylsulfonamido)-3-phenylpropanoate | 203873-70-5

• 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: (S)-methyl 2-(N-allyl-2-nitrophenylsulfonamido)-3-phenylpropanoate
• 英文别名: methyl (2S)-2-[(2-nitrophenyl)sulfonyl-prop-2-enylamino]-3-phenylpropanoate
• CAS: 203873-70-5
• 化学式: C₁₉H₂₀N₂O₆S
• 分子量: 404.444
• InChiKey: XXLHYHLAAPRQRJ-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-methyl 2-(N-allyl-2-nitrophenylsulfonamido)-3-phenylpropanoate 在 potassium carbonate 、 苯硫酚 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以72%的产率得到N-allylated phenylalanine methyl ester
  参考文献：
  名称：

  固液PTC条件下α-氨基酸酯的N-单烷基化

  摘要：

  N-(2-硝基苯磺酰基)-(o-NBS-AA-OMe, 4) 和 N-(4-硝基苯磺酰基)-α-氨基酸甲酯 (p-NBS-AA-OMe, 5) 用多种烷基卤化物 6 在固液相转移催化 (SL-PTC) 条件下，得到烷基化产物 o-NBS-N-R2-AA-OMe 7 和 p-NBS-N-R2-AA-OMe 8在没有任何可检测到的外消旋化的情况下以优异的产量获得

  DOI：

  10.1002/(sici)1099-0690(200004)2000:8<1443::aid-ejoc1443>3.0.co;2-5
• 作为产物：
  描述：

  L-苯丙氨酸甲酯 在 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-methyl 2-(N-allyl-2-nitrophenylsulfonamido)-3-phenylpropanoate
  参考文献：
  名称：

  Site-specific N-alkylation of peptides on the solid phase

  摘要：

  A convenient approach, featuring a Mitsunobu reaction, is described for the introduction of an alkyl group at a specific amide function of a peptide on the solid phase. This 'site-specific alkylation' procedure is illustrated with an N-ethyl scan of Leu-enkephalin. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10766-3

文献信息

• DBU Catalysed Enantioselective Degradative Rearrangement: a Way to Tetrasubstituted 2‐Aryl‐2‐Amino Esters
  作者：Camilla Loro、Roberto Sala、Michele Penso、Francesca Foschi

  DOI：10.1002/adsc.202100493

  日期：2021.8.13

  Na2CO3. Under very mild reaction conditions, without using metal or chiral additives, this heterogeneous system promotes the degradative rearrangement of functionalized N-aryl sulphonyl α-amino esters into the corresponding tetrasubstituted 2-aryl-2-amino esters, with high enantiomeric ratios (up to 97.5:2.5) and good yields (up to 95%).

  在此，我们报告了一种催化、易于扩展的协议，用于四取代的 α-芳基-α-氨基酸衍生物的对映选择性合成，使用由 DME 中的催化 DBU 和 Na 2 CO 3水溶液组成的双相系统。在非常温和的反应条件下，不使用金属或手性添加剂，这种多相系统促进官能化N-芳基磺酰基 α-氨基酯降解重排成相应的四取代 2-芳基-2-氨基酯，具有高对映体比（高达97.5:2.5) 和良好的产量（高达 95%）。
• N-Monoalkylation of α-Amino Acid Esters under Solid-Liquid PTC Conditions
  作者：Domenico Albanese、Dario Landini、Vittoria Lupi、Michele Penso

  DOI：10.1002/(sici)1099-0690(200004)2000:8<1443::aid-ejoc1443>3.0.co;2-5

  日期：2000.4

  N-(2-Nitrophenylsulfonyl)- (o-NBS-AA-OMe, 4) and N-(4-Nitrophenylsulfonyl)-α-amino acid methyl esters (p-NBS-AA-OMe, 5) were N-alkylated with a variety of alkyl halides 6 under solid-liquid phase-transfer catalysis (SL-PTC) conditions, affording the alkylated products o-NBS-N-R2-AA-OMe 7 and p-NBS-N-R2-AA-OMe 8 in excellent yields without any detectable racemization.

  N-(2-硝基苯磺酰基)-(o-NBS-AA-OMe, 4) 和 N-(4-硝基苯磺酰基)-α-氨基酸甲酯 (p-NBS-AA-OMe, 5) 用多种烷基卤化物 6 在固液相转移催化 (SL-PTC) 条件下，得到烷基化产物 o-NBS-N-R2-AA-OMe 7 和 p-NBS-N-R2-AA-OMe 8在没有任何可检测到的外消旋化的情况下以优异的产量获得
• 3,5-Bis(n-perfluorooctyl)benzyltriethylammonium Bromide (F-TEBA): An Efficient, Easily Recoverable Fluorous Catalyst for Solid-Liquid PTC Reactions
  作者：Gianluca Pozzi、Voichiţa Mihali、Francesca Foschi、Michele Penso、Silvio Quici、Richard H. Fish

  DOI：10.1002/adsc.200900631

  日期：2009.12

  reacted under mild conditions to give 3,5-bis(n-perfluorooctyl)benzyltriethylammonium bromide (F-TEBA), an analogue of the versatile phase-transfer catalyst, benzyltriethylammonium chloride (TEBA), containing two fluorous ponytails. This perfluoroalkylated quaternary ammonium salt was successfully employed as a catalyst in a variety of reactions run under solid-liquid phase-transfer catalysis (SL-PTC) conditions

  在温和的条件下，将易于获得的3,5-双（全氟辛基）苄基溴与三乙胺反应，得到3,5-双（n-全氟辛基）苄基三乙基溴化铵（F-TEBA），这是通用相转移催化剂的类似物，苄基三乙基氯化铵（TEBA），含有两个氟马尾辫。在固体-液相转移催化（SL-PTC）条件下进行的各种反应中，这种全氟烷基化的季铵盐已成功用作催化剂。因此，F-TEBA具有疏水性和疏脂性，可以定量收率快速回收，并可以在多个反应周期内无损失活性的情况下重复使用。
• Site-specific N-alkylation of peptides on the solid phase
  作者：John F. Reichwein、Rob M.J. Liskamp

  DOI：10.1016/s0040-4039(97)10766-3

  日期：1998.3

  A convenient approach, featuring a Mitsunobu reaction, is described for the introduction of an alkyl group at a specific amide function of a peptide on the solid phase. This 'site-specific alkylation' procedure is illustrated with an N-ethyl scan of Leu-enkephalin. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Microwave-accelerated cross-metathesis reactions of N-allyl amino acid substrates
  作者：Sally-Ann Poulsen、Laurent F. Bornaghi

  DOI：10.1016/j.tetlet.2005.08.126

  日期：2005.10

  Microwave heating has been utilised for the cross-metathesis reaction of N-allyl amino acid substrates to generate olefin homodimers. Remarkable acceleration of the cross-metathesis reaction (minutes compared to hours) over conventional reflux heating was observed. In addition, improved reaction yields and similar E/Z ratios for the cross-metathesis products were achieved. (c) 2005 Published by Elsevier Ltd.