meso-1-((benzyloxy)carbonyl)piperidine-2,6-dicarboxylic acid | 59234-43-4

• 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: meso-1-((benzyloxy)carbonyl)piperidine-2,6-dicarboxylic acid
• 英文别名: N-carbobenzoxypiperidine-cis-2,6-dicarboxylic acid；N-Z-piperidine-cis-2,6-dicarboxylic acid；(2R,6S)-1-[(benzyloxy)carbonyl]-2,6-piperidinedicarboxylic acid；(2R,6S)-1-phenylmethoxycarbonylpiperidine-2,6-dicarboxylic acid
• CAS: 59234-43-4
• 化学式: C₁₅H₁₇NO₆
• 分子量: 307.303
• InChiKey: YXDQKTBJURVLSM-TXEJJXNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  meso-1-((benzyloxy)carbonyl)piperidine-2,6-dicarboxylic acid 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到N-carbobenzoxy-cis-2,6-bis(hydroxymethyl)piperidine
  参考文献：
  名称：

  Enzyme-catalysed hydrolysis of N-benzyloxycarbonyl-cis-2,6-(acetoxymethyl)piperidine. A facile route to optically active piperidines

  摘要：

  We report the first enzymatic asymmetrization of a piperidine system. Hydrolysis of N-benzyloxycarbonyl-cis-2,6-(acetoxymethyl)piperidine in the presence of Aspergillus niger lipase gave the corresponding 2R, 6S mono-acetate in good chemical yield and very high optical purity (ee greater-than-or-equal-to 98%).

  DOI：

  10.1016/s0957-4166(00)86034-6
• 作为产物：
  描述：

  吡啶-2,6-二甲酸 在 platinum(IV) oxide 、 氢气 、 溶剂黄146 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 59.0h， 生成 meso-1-((benzyloxy)carbonyl)piperidine-2,6-dicarboxylic acid
  参考文献：
  名称：

  Remote conformational responses to enantiomeric excess in carboxylate-binding dynamic foldamers

  摘要：

  一种锌(ii)-封顶的Aib寡聚体可以感知对映体过量，并将这一信息传递给远程的报告基团，提供¹H光谱输出。

  DOI：

  10.1039/c9cc03895g

文献信息

• Design, Synthesis, and Biological Activity of Novel Polycyclic Aza-Amide FKBP12 Ligands
  作者：Raymond A. Hudack,、Nancy S. Barta、Chuangxing Guo、Judith Deal、Liming Dong、Lorraine K. Fay、Bradley Caprathe、Arindam Chatterjee、Darin Vanderpool、Christopher Bigge、Richard Showalter、Steve Bender、Corinne E. Augelli-Szafran、Elizabeth Lunney、Xinjun Hou

  DOI：10.1021/jm049161u

  日期：2006.2.1

  Since the discovery that FK-506 promotes neurite outgrowth, considerable attention has been focused on the development of potent nonimmunosuppressive ligands for FK-506 binding proteins (FKBPs). Such neuroimmunophilin agents have been reported to show neuroregenerative activity in a variety of cell and animal models including neurite outgrowth, age-related cognitive decline, Parkinson's disease, peripheral nerve injury, optic nerve degeneration, and diabetic neuropathy. We have designed and synthesized a unique series of tetracyclic aza-amides that have been shown to be potent FKBP12 rotamase inhibitors. The structure-activity relationships established in this study have demonstrated diverse structural modifications that result in potent rotamase inhibitory activity.
• A concise synthesis of AG5473/5507 utilizing N-acyliminium ion chemistry
  作者：Chuangxing Guo、Siegfried Reich、Rich Showalter、Ernie Villafranca、Liming Dong

  DOI：10.1016/s0040-4039(00)00846-7

  日期：2000.7

  FKBP-12 inhibitors AG5473 and AG5507 were resynthesized through a more efficient Ii-step sequence. The key steps involved propargyl trimethylsilane addition to an N-acyliminium ion, ozonolysis of the allene and acid-catalyzed cyclization. A mild protocol for introducing a formaldehyde moiety to an anomeric center was established. The synthetic materials were evaluated in the FKBP rotamase assay. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis and Evaluation of Novel Macrocyclic and Acyclic Ligands as Contrast Enhancement Agents for Magnetic Resonance Imaging
  作者：Hyun-Soon Chong、Kayhan Garmestani、L. Henry Bryant,、Diane E. Milenic、Terrish Overstreet、Noah Birch、Thien Le、Erik D. Brady、Martin W. Brechbiel

  DOI：10.1021/jm051009k

  日期：2006.3.1

  Novel chelates PIP-DTPA, AZEP-DTPA, NETA, NPTA, and PIP-DOTA were synthesized and evaluated as potential magnetic resonance imaging (MRI) contrast enhancement agents. The T-1 and T-2 relaxivities of their corresponding Gd(III) complexes are reported. At clinically relevant field strengths, the relaxivities of the complexes are comparable to that of the clinically used contrast agents Gd(DTPA) and Gd(DOTA). The serum stability of the Gd-153-labeled complexes, Gd(PIP-DTPA), Gd(AZEP-DTPA), Gd(PIP-DOTA), Gd(NETA), and Gd(NPTA), was assessed by measuring the release of Gd-153 from the complexes. Gd-153(NETA), Gd-153(PIP-DTPA), and Gd-153(PIP-DOTA) were found to be stable in human serum for up to 14 days without any measurable loss of radioactivity. Significant release of Gd-153 was observed with the Gd-153(III) radiolabled NPTA. In vivo biodistribution of the Gd-153-labeled complexes was performed to evaluate their in vivo stability. While Gd(AZEP-DTPA) and Gd(NPTA) were found to be unstable in vivo, Gd(NETA), Gd(PIP-DTPA), and Gd(PIP-DOTA) were excreted without dissociation. These results suggest that the Gd(III) complexes of the novel chelates NETA, PIP-DTPA, and PIP-DOTA possess potential as MRI contrast enhancement agents. In particular, the piperidine backboned chelates Gd(PIP-DTPA) and Gd(PIP-DOTA) displayed reduced kidney retention as compared to the nonspecific MRI contrast agent Gd(DOTA) at all time points, although the observed effects were relatively small at 0.5 h postinjection. Incorporation of the lipophilic piperidine ring appears to confer a moderate effect on the liver uptake of these two chelates.
• Remote conformational responses to enantiomeric excess in carboxylate-binding dynamic foldamers
  作者：Natasha Eccles、Bryden A. F. Le Bailly、Flavio della Sala、Iñigo J. Vitórica-Yrezábal、Jonathan Clayden、Simon J. Webb

  DOI：10.1039/c9cc03895g

  日期：——

  A zinc(ii)-capped Aib oligomer senses enantiomeric excess and transmits this information to a remote reporter group which provides a ¹H spectroscopic output.

  一种锌(ii)-封顶的Aib寡聚体可以感知对映体过量，并将这一信息传递给远程的报告基团，提供¹H光谱输出。
• Enzyme-catalysed hydrolysis of N-benzyloxycarbonyl-cis-2,6-(acetoxymethyl)piperidine. A facile route to optically active piperidines
  作者：Robert Chênevert、Michael Dickman

  DOI：10.1016/s0957-4166(00)86034-6

  日期：1992.8

  We report the first enzymatic asymmetrization of a piperidine system. Hydrolysis of N-benzyloxycarbonyl-cis-2,6-(acetoxymethyl)piperidine in the presence of Aspergillus niger lipase gave the corresponding 2R, 6S mono-acetate in good chemical yield and very high optical purity (ee greater-than-or-equal-to 98%).