methyl (R)-N-(tert-butoxycarbonyl)-5-oxopiperidine-2-carboxylate | 448963-98-2

• 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 (R)-N-(tert-butoxycarbonyl)-5-oxopiperidine-2-carboxylate
• 英文别名: (R)-1-tert-butyl 2-Methyl 5-oxopiperidine-1,2-dicarboxylate；1-O-tert-butyl 2-O-methyl (2R)-5-oxopiperidine-1,2-dicarboxylate
• CAS: 448963-98-2
• 化学式: C₁₂H₁₉NO₅
• 分子量: 257.287
• InChiKey: UCRLFGKYCFXSEA-SECBINFHSA-N

物化性质

• 沸点：
  350.0±42.0 °C(Predicted)
• 密度：
  1.175±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (R)-N-(tert-butoxycarbonyl)-5-oxopiperidine-2-carboxylate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 1-(tert-butyl) 2-methyl (2R,5R)-5-hydroxypiperidine-1,2-dicarboxylate
  参考文献：
  名称：

  Synthesis and biological activity of selective pipecolic acid-based TNF-α converting enzyme (TACE) inhibitors

  摘要：

  A series of novel, selective TNF-alpha converting enzyme inhibitors based on 4-hydroxy and 5-hydroxy pipecolate hydroxamic acid scaffolds is described. The potency and selectivity of TACE inhibition is dramatically influenced by the nature of the sulfonamide group which interacts with the S1' site of the enzyme, Substituted 4-benzyloxybenzenesulfonamides exhibit excellent TACE potency with > 100x selectivity over inhibition of matrix metalloprotease-1 (MMP-1). Alkyl substituents on the ortho position of the benzyl ether moiety give the most potent inhibition of TNF-alpha release in LPS-treated human whole blood. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00183-x
• 作为产物：
  描述：

  BOC-D-焦谷氨酸甲酯 在 Ph₂(OAc)4 正丁基锂 作用下， 以 乙醚 、 苯 为溶剂， 生成 methyl (R)-N-(tert-butoxycarbonyl)-5-oxopiperidine-2-carboxylate
  参考文献：
  名称：

  Synthesis and biological activity of selective pipecolic acid-based TNF-α converting enzyme (TACE) inhibitors

  摘要：

  A series of novel, selective TNF-alpha converting enzyme inhibitors based on 4-hydroxy and 5-hydroxy pipecolate hydroxamic acid scaffolds is described. The potency and selectivity of TACE inhibition is dramatically influenced by the nature of the sulfonamide group which interacts with the S1' site of the enzyme, Substituted 4-benzyloxybenzenesulfonamides exhibit excellent TACE potency with > 100x selectivity over inhibition of matrix metalloprotease-1 (MMP-1). Alkyl substituents on the ortho position of the benzyl ether moiety give the most potent inhibition of TNF-alpha release in LPS-treated human whole blood. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00183-x

文献信息

• Asymmetric Synthesis of 4- and 5-Substituted Pipecolic Esters by Ring-Closing Metathesis and Palladium-Catalyzed Formate Reduction
  作者：Chong-Si Sun、Yu-Shiang Lin、Duen-Ren Hou

  DOI：10.1021/jo8008885

  日期：2008.9.1

  Asymmetric synthesis of 4- and 5-substituted pipecolic esters was achieved by the sequence of allylation, ring-closing metathesis, and palladium-catalyzed formate reduction.
• NEW ANTIBIOTICS TARGETING MYCOBACTERIA
  申请人：ASSISTANCE PUBLIQUE-HOPITAUX DE PARIS

  公开号：US20200325139A1

  公开（公告）日：2020-10-15

  The present invention relates to a compound of the folowing formula (I) or a pharmaceutically acceptable salt and/or solvate thereof, notably for use as a dmg, notably in the treatment of a disease caused by mycobacteria, as well as pharmaceutical compositions containing such a compound and a process to prepare such a compound.
• Synthesis and biological activity of selective pipecolic acid-based TNF-α converting enzyme (TACE) inhibitors
  作者：Michael A. Letavic、Matt Z. Axt、John T. Barberia、Thomas J. Carty、Dennis E. Danley、Kieran F. Geoghegan、Nadia S. Halim、Lise R. Hoth、Ajith V. Kamath、Ellen R. Laird、Lori L. Lopresti-Morrow、Kim F. McClure、Peter G. Mitchell、Vijayalakshmi Natarajan、Mark C. Noe、Jayvardhan Pandit、Lisa Reeves、Gayle K. Schulte、Sheri L. Snow、Francis J. Sweeney、Douglas H. Tan、Chul H. Yu

  DOI：10.1016/s0960-894x(02)00183-x

  日期：2002.5

  A series of novel, selective TNF-alpha converting enzyme inhibitors based on 4-hydroxy and 5-hydroxy pipecolate hydroxamic acid scaffolds is described. The potency and selectivity of TACE inhibition is dramatically influenced by the nature of the sulfonamide group which interacts with the S1' site of the enzyme, Substituted 4-benzyloxybenzenesulfonamides exhibit excellent TACE potency with > 100x selectivity over inhibition of matrix metalloprotease-1 (MMP-1). Alkyl substituents on the ortho position of the benzyl ether moiety give the most potent inhibition of TNF-alpha release in LPS-treated human whole blood. (C) 2002 Elsevier Science Ltd. All rights reserved.