cis-2,6-piperidinedicarboxylic acid | 429661-20-1

• 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: cis-2,6-piperidinedicarboxylic acid
• 英文别名: cis-piperidine-2,6-dicarboxylic acid；piperidine-cis-2,6-dicarboxylic acid；(2R,6S)-6-carboxypiperidin-1-ium-2-carboxylate
• CAS: 429661-20-1
• 化学式: C₇H₁₁NO₄
• 分子量: 173.169
• InChiKey: SOOPBZRXJMNXTF-SYDPRGILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  cis-2,6-piperidinedicarboxylic acid 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 dimethyl sulfide borane 、 氢气 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 二甲基亚砜 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 90.0 ℃ 、206.84 kPa 条件下， 反应 223.0h， 生成 2-[(1R,11S)-3,9,15-tris(carboxymethyl)-3,6,9,15-tetrazabicyclo[9.3.1]pentadecan-6-yl]acetic acid
  参考文献：
  名称：

  Synthesis and Evaluation of Novel Macrocyclic and Acyclic Ligands as Contrast Enhancement Agents for Magnetic Resonance Imaging

  摘要：

  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.

  DOI：

  10.1021/jm051009k
• 作为产物：
  描述：

  cis-2,6-piperidinedicarboxamide 在 barium dihydroxide 作用下， 以 水 为溶剂， 反应 2.0h， 以79%的产率得到cis-2,6-piperidinedicarboxylic acid
  参考文献：
  名称：

  Synthesis of a key intermediate in the diaminopimelate pathway to L-Lysine: 2,3,4,5-tetrahydrodipicolinic acid

  摘要：

  2,3,4,5-Tetrahydrodipicolinic acid (3) is a key intermediate in the diaminopimelate (DAP) pathway to L-lysine (7). It was synthesized as the stable racemic potassium salt (25) from dipicolinic acid (14) by esterification, hydrogenation to the cis-diester (17), followed by elimination of p-toluenesuifinic acid from the N-toluenesulfonyl derivative (24) of dimethyl cis-piperidine-2,6-dicarboxylate with concomitant cleavage of the ester groups. (+/-)-2,3,4,5-Tetrahydrodipicolinic acid is unstable in neutral or acidic solution, and in basic solution it exists in equilibrium with the corresponding enamine (27) and 2-oxo-6-aminoadipate (26).

  DOI：

  10.1016/0040-4020(95)00618-i

文献信息

• [EN] PROTECTED ORGANOBORONIC ACIDS WITH TUNABLE REACTIVITY, AND METHODS OF USE THEREOF<br/>[FR] ACIDES ORGANOBORONIQUES PROTÉGÉS À RÉACTIVITÉ AJUSTABLE ET LEURS PROCÉDÉS D'UTILISATION
  申请人：UNIV ILLINOIS

  公开号：WO2017027435A1

  公开（公告）日：2017-02-16

  Disclosed are a range of protected organoboronic acid reagents useful in the modular assembly of complex organic compounds. The reactivities of the protected organoboronic acid reagents may be varied predictably by changes to the number and identities of their substituents. Also disclosed are methods of using the protected organoboronic acid reagents in the synthesis of organic compounds.

  本文披露了一系列受保护的有机硼酸试剂，可用于复杂有机化合物的模块化组装。这些受保护的有机硼酸试剂的反应性可以通过改变它们的取代基的数量和身份来可预测地变化。同时还披露了在有机化合物的合成中使用这些受保护的有机硼酸试剂的方法。
• Bicyclic piperazines as metabotropic glutatmate receptor antagonists
  申请人：Edwards Louise

  公开号：US20070037816A1

  公开（公告）日：2007-02-15

  The invention relates to compounds of formula I or pharmaceutically acceptable salts or solvates thereof: where Ar 1 , A, Hy, R 1 , m and n are as defined in the description. The invention also includes pharmaceutical compositions and uses of, and processes of making the compounds, as well as methods of medical treatment of mGluR5-mediated disorders.

  该发明涉及公式I的化合物或其药用可接受的盐或溶剂化合物：其中Ar1、A、Hy、R1、m和n如描述中所定义。该发明还包括药物组合物、使用方法以及制备这些化合物的方法，以及治疗mGluR5介导的疾病的医疗方法。
• MODIFIER FOR AROMATIC POLYESTER AND AROMATIC POLYESTER RESIN COMPOSITION COMPRISING THE SAME
  申请人：TABATA Masayoshi

  公开号：US20110224343A1

  公开（公告）日：2011-09-15

  The present invention provides a modifier for aromatic polyesters which enhances the melt fluidity of aromatic polyesters without a significant decrease in the heat resistance of the aromatic polyesters, and an aromatic polyester resin composition including the modifier for aromatic polyesters. The present invention relates to a modifier for aromatic polyesters comprising polyhydric phenol residues and residues of aromatic polycarboxylic acid, acid halide or acid anhydride thereof, and the modifier comprises a material having a structure composed of a first residue selected from the group consisting of divalent residues represented by Formula (I): —Ar—W 1 x —Ar— and by Formula (II): —Ar—, the first residues being bonded to two identical or different second residues selected from the group consisting of monovalent residues represented by Formula (III): and monovalent residues represented by Formula (IV): —O—C(O)—R 7 —.

  本发明提供了一种用于芳香族聚酯的改性剂，可以增强芳香族聚酯的熔融流动性，而不明显降低芳香族聚酯的耐热性，以及包括该改性剂的芳香族聚酯树脂组合物。本发明涉及一种用于芳香族聚酯的改性剂，包括多羟基酚残基和芳香族多羧酸、酸卤或其酸酐残基，该改性剂包括具有以下结构的材料：第一残基，选择自由式(I)所代表的二价残基：—Ar—W1x—Ar—和自由式(II)所代表的：—Ar—，第一残基与选择自由式(III)所代表的单价残基：和自由式(IV)所代表的单价残基：—O—C(O)—R7—的两个相同或不同的第二残基结合。
• Stereo-Selective Preparation of Teneraic Acid, &lt;i&gt;trans&lt;/i&gt;-(2&lt;i&gt;S&lt;/i&gt;,6&lt;i&gt;S&lt;/i&gt;)-Piperidine-2,6-dicarboxylic Acid, &lt;i&gt;via&lt;/i&gt; Anodic Oxidation and Cobalt-Catalyzed Carbonylation
  作者：Yusuke Amino、Seiichi Nishi、Kunisuke Izawa

  DOI：10.1248/cpb.c17-00391

  日期：——

  Teneraic acid (piperidine-2,6-dicarboxylic acid) is a naturally occurring imino acid that comprises three stereoisomers due to its two asymmetric centers at C2 and C6. The configuration of natural teneraic acid is reported to correspond to trans-(2S,6S). However, a few studies are focused on the stereospecific synthesis of trans-(2S,6S)-teneraic acid. The present study investigates a convenient synthetic

  硬脂酸（哌啶-2,6-二羧酸）是一种天然存在的亚氨基酸，由于其在C2和C6的两个不对称中心而包含三个立体异构体。据报道，天然腱酸的构型对应于反式（2S，6S）。然而，一些研究集中在反式-（2S，6S）-戊酸的立体有择合成上。本研究研究了一种方便的合成方法，该方法包括区域特异性阳极氧化和立体特异性钴催化的羰基化反应以获得反式（2S，6S）-戊酸。（S）-N-苯甲酰基-α-甲氧基哌酸甲酯是甲基（S）-N的阳极氧化反应，它显示出与分子内酰胺羰基化的中间体（N-α-羟烷基酰胺）相对应的结构的关键中间体。 -苯甲酰基哌酸酯。随后，钴催化的羰基化将（S）-N-苯甲酰基-α-甲氧基哌酸甲酯以良好的光学纯度（> 95％对映体过量（ee））转化为反式（2S，6S）-N-苯甲酰基-戊酸二甲酯中等收率（63％）。最后，通过酸性水解进行脱保护反应以获得反-（2S，6S）-戊酸。通过比较其物理性质与先前报道的顺式-
• ACE-2 modulating compounds and methods of use thereof
  申请人：——

  公开号：US20040082496A1

  公开（公告）日：2004-04-29

  ACE-2 modulating compounds for the treatment of body weight disorders are disclosed. Methods of using the compounds and pharmaceutical compositions containing the compounds are also claimed.

  抗ACE-2调节化合物用于治疗体重失调的方法已被披露。还声称了使用这些化合物的方法和含有这些化合物的药物组合物。