tert‑butyl (S)‑2‑(p‑tolylcarbamoyl)pyrrolidine‑1‑carboxylate | 52815-83-5

• 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: tert‑butyl (S)‑2‑(p‑tolylcarbamoyl)pyrrolidine‑1‑carboxylate
• 英文别名: tert-Butyloxycarbonyl-L-prolyl-p-methylanilin；t-Butyl (s)-2-(p-tolylcarbamoyl)pyrrolidine-1-carboxylate；tert-butyl (2S)-2-[(4-methylphenyl)carbamoyl]pyrrolidine-1-carboxylate
• CAS: 52815-83-5
• 化学式: C₁₇H₂₄N₂O₃
• 分子量: 304.389
• InChiKey: RKYIEPATGAUQPC-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert‑butyl (S)‑2‑(p‑tolylcarbamoyl)pyrrolidine‑1‑carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (S)-N-(4-methylphenyl)pyrrolidine-2-carboxamide
  参考文献：
  名称：

  ( S )-1-甲酰基吡咯烷-2-羧酸衍生物的合成和催化活性对酮和酮亚胺的对映选择性还原

  摘要：

  一系列 (S)-1-甲酰基吡咯烷-2-羧酸衍生物 (6a-t) 已被合成并作为手性有机催化剂用于酮 2 和酮亚胺 3 的不对称还原。这些有机活化剂提供了良好到中等的对映选择性酮和酮亚胺的不对称还原。其中，有机活化剂6h显示出最佳的效率，在酮的还原中提供了84％的收率和41％的ee，在酮亚胺的还原中提供了75％的收率和52％的ee。

  DOI：

  10.3184/030823408x318433
• 作为产物：
  描述：

  BOC-L-脯氨酸 、 乙烷,三氯氟- 在 Candida antarctica lipase immobilized on acrylic resin 作用下， 以 正庚烷 为溶剂， 反应 72.0h， 以72%的产率得到tert‑butyl (S)‑2‑(p‑tolylcarbamoyl)pyrrolidine‑1‑carboxylate
  参考文献：
  名称：

  CAL-B 介导的苯氧基和芳基丙酸直接酰胺化有效合成一组有价值的酰胺

  摘要：

  报道了在 CAL-B 的辅助下，作为可生物降解的催化剂，一组未活化的羧酸与苯胺的高效、简单和可持续的酰胺化。酶酰胺化反应是在一组非甾体抗炎药 (NSAID)、苯氧基丙酸和受保护的脯氨酸上进行的，方法是在 80°C 下反应 72 小时后，在庚烷中直接缩合一当量羧酸和两当量苯胺衍生物. 回收得到的羧酰胺，分离的化学产率介于中等和极好之间。首次报道了其中的14个，得到了X射线晶体：N-(4-碘苯基)-2-(4-异丁基苯基)丙酰胺1d。

  DOI：

  10.1007/s11696-021-01636-5

文献信息

• Simple, inexpensive, and facile l-prolinamide used as a recyclable organocatalyst for highly efficient large-scale asymmetric direct aldol reactions
  作者：Jiangwei Xu、Xiangkai Fu、Chuanlong Wu、Xiaoyan Hu

  DOI：10.1016/j.tetasy.2011.05.008

  日期：2011.4

  In order to discover a simple, inexpensive, and efficient route to obtain highly enantiomerically enriched anti-aldol products for applications in industry, a series of prolinamides 1-5 with different carbocyclic rings have been synthesized from achiral cycloalkylamine, and prolinamides 6-9 have been synthesized from aniline with different substituents. The organocatalysts obtained catalyzed the asymmetric aldol reaction and showed that no matter carbocyclic rings or aromatic rings were found to play a significant role in the formation of the aldol products. Moreover, the prolinamide 6 exhibited efficient catalytic activity in the asymmetric aldol reaction only with 5 mol % catalyst loading and 4 equiv of ketone, and afforded aldol products in high diastereoselectivity (up to anti/syn 99:1) and enantioselectivity (99%) and significantly enhanced the reaction yield (99%). These results were much better than L-proline-3-nitroanilide which had the strongest electron-withdrawing group on the aromatic ring. Furthermore, catalyst 6 can be easily recovered and reused, without a significant decrease of enantioselectivity after five cycles. This inexpensive, simple, and recyclable catalyst can be efficiently used in large-scale reactions with the enantioselectivities being maintained at the same level, which offers a great possibility for application in industry. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis of Analogues of <scp>BCTC</scp> Incorporating a Pyrrolidinyl Linker and Biological Evaluation as Transient Receptor Potential Vanilloid 1 Antagonists
  作者：Lin Yan、Jingjie Wang、Miaobo Pan、Qianqian Qiu、Wenlong Huang、Hai Qian

  DOI：10.1111/cbdd.12661

  日期：2016.2

  A series of novel pyrrolidinyl linker TRPV1 antagonists were prepared in an effort to lower the hyperthermic side‐effects of first‐generation antagonist BCTC. These compounds were investigated for antagonism of hTRPV1 activation by capsaicin and acid in vitro. Preliminary results suggested the compounds 10a, 10b, 10c and 10j had favorable TRPV1 antagonism activity. In further studies in vivo, 10b, comparable to BCTC, showed potent analgesic activity in capsaicin‐induced and heat‐induced pain models. In addition, 10b indicated a reduced risk of body temperature elevation. All of these demonstrated that 10b can be considered as a safe candidate for the further development of analgesic drugs.
• CAL-B-mediated efficient synthesis of a set of valuable amides by direct amidation of phenoxy- and aryl-propionic acids
  作者：Nourelhouda Benamara、Mounia Merabet-Khelassi、Louisa Aribi-Zouioueche、Olivier Riant

  DOI：10.1007/s11696-021-01636-5

  日期：2021.8

  efficient, easy and sustainable amidation of a set of non-activated carboxylic acids with anilines, assisted by CAL-B, as biodegradable catalyst, is reported. The enzymatic amidation reactions are performed on set of nonsteroidal anti-inflammatory drugs (NSAIDs), phenoxypropionic acid and protected-prolines by direct condensation of one equivalent of carboxylic acids and two equivalents of anilines

  报道了在 CAL-B 的辅助下，作为可生物降解的催化剂，一组未活化的羧酸与苯胺的高效、简单和可持续的酰胺化。酶酰胺化反应是在一组非甾体抗炎药 (NSAID)、苯氧基丙酸和受保护的脯氨酸上进行的，方法是在 80°C 下反应 72 小时后，在庚烷中直接缩合一当量羧酸和两当量苯胺衍生物. 回收得到的羧酰胺，分离的化学产率介于中等和极好之间。首次报道了其中的14个，得到了X射线晶体：N-(4-碘苯基)-2-(4-异丁基苯基)丙酰胺1d。
• Synthesis and Catalytic Activities of (<i>S</i>)-1-formylpyrrolidine-2-carboxylic Acid Derivatives for the Enantioselective Reductions of Both a Ketone and a Ketimine
  作者：Zhenfei Chen、Anjiang Zhang、Lixue Zhang、Jing Zhang、Xinxiang Lei

  DOI：10.3184/030823408x318433

  日期：2008.5

  as chiral organocatalysts in the asymmetric reduction of both ketone 2 and ketimine 3. These organic activators afforded good to moderate enantioselectivities in the asymmetric reductions of both the ketone and the ketimine. Among them, organic activator 6h displayed the best efficiency, affording a 84% yield and 41% ee in the reduction of the ketone and 75% yield and 52% ee in the reduction of the ketimine

  一系列 (S)-1-甲酰基吡咯烷-2-羧酸衍生物 (6a-t) 已被合成并作为手性有机催化剂用于酮 2 和酮亚胺 3 的不对称还原。这些有机活化剂提供了良好到中等的对映选择性酮和酮亚胺的不对称还原。其中，有机活化剂6h显示出最佳的效率，在酮的还原中提供了84％的收率和41％的ee，在酮亚胺的还原中提供了75％的收率和52％的ee。