(S)-benzyl-1-((R)-1-phenylethyl)-5-thioxopyrrolidine-3-carboxylate | 949149-62-6

• 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: (S)-benzyl-1-((R)-1-phenylethyl)-5-thioxopyrrolidine-3-carboxylate
• 英文别名: benzyl (S)-1-((R)-1-phenylethyl)-5-thioxopyrrolidine-3-carboxylate；benzyl (3S)-1-[(1R)-1-phenylethyl]-5-sulfanylidenepyrrolidine-3-carboxylate
• CAS: 949149-62-6
• 化学式: C₂₀H₂₁NO₂S
• 分子量: 339.458
• InChiKey: VEKBQVLNLQRUOR-QAPCUYQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-benzyl-1-((R)-1-phenylethyl)-5-thioxopyrrolidine-3-carboxylate 在 palladium on activated charcoal 氢气 、 碘甲烷 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 43.0h， 生成 (R)-3-羧基吡咯烷
  参考文献：
  名称：

  A rapid and convenient synthesis of β-proline

  摘要：

  A short, reliable, and cheap synthesis of both enantiomers of P-proline, an efficient organocatalyst and all important building block in medicinal chemistry, has been developed in four steps (overall yield: 72%) from the diasteromeric adducts of methyl itaconate and (R)-alpha-methylbenzylamine. The key step involves the chemoselective reduction of a lactam group in the presence of a benzyl ester. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.06.106
• 作为产物：
  描述：

  衣康酸二甲酯 在 劳森试剂 、 APTS 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 20.0h， 生成 (S)-benzyl-1-((R)-1-phenylethyl)-5-thioxopyrrolidine-3-carboxylate
  参考文献：
  名称：

  A rapid and convenient synthesis of β-proline

  摘要：

  A short, reliable, and cheap synthesis of both enantiomers of P-proline, an efficient organocatalyst and all important building block in medicinal chemistry, has been developed in four steps (overall yield: 72%) from the diasteromeric adducts of methyl itaconate and (R)-alpha-methylbenzylamine. The key step involves the chemoselective reduction of a lactam group in the presence of a benzyl ester. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.06.106

文献信息

• Design of novel HIV-1 protease inhibitors incorporating isophthalamide-derived P2-P3 ligands: Synthesis, biological evaluation and X-ray structural studies of inhibitor-HIV-1 protease complex
  作者：Arun K. Ghosh、Margherita Brindisi、Prasanth R. Nyalapatla、Jun Takayama、Jean-Rene Ella-Menye、Sofiya Yashchuk、Johnson Agniswamy、Yuan-Fang Wang、Manabu Aoki、Masayuki Amano、Irene T. Weber、Hiroaki Mitsuya

  DOI：10.1016/j.bmc.2017.04.005

  日期：2017.10

  Based upon molecular insights from the X-ray structures of inhibitor-bound HIV-1 protease complexes, we have designed a series of isophthalamide-derived inhibitors incorporating substituted pyrrolidines, piperidines and thiazolidines as P2-P3 ligands for specific interactions in the S2-S3 extended site. Compound 4b has shown an enzyme K-i of 0.025 nM and antiviral IC50 of 69 nM. An X-ray crystal structure of inhibitor 4b-HIV-1 protease complex was determined at 1.33 angstrom resolution. We have also determined X-ray structure of 3b-bound HIV-1 protease at 1.27 angstrom resolution. These structures revealed important molecular insight into the inhibitor-HIV-1 protease interactions in the active site. (C) 2017 Elsevier Ltd. All rights reserved.
• A rapid and convenient synthesis of β-proline
  作者：Jérôme Blanchet、Mickael Pouliquen、Marie-Claire Lasne、Jacques Rouden

  DOI：10.1016/j.tetlet.2007.06.106

  日期：2007.8

  A short, reliable, and cheap synthesis of both enantiomers of P-proline, an efficient organocatalyst and all important building block in medicinal chemistry, has been developed in four steps (overall yield: 72%) from the diasteromeric adducts of methyl itaconate and (R)-alpha-methylbenzylamine. The key step involves the chemoselective reduction of a lactam group in the presence of a benzyl ester. (c) 2007 Elsevier Ltd. All rights reserved.