3-氨基-1-金刚烷羧酸甲酯 | 80103-18-0

• 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
• 中文名称: 3-氨基-1-金刚烷羧酸甲酯
• 中文别名: 3-氨基金刚烷-1-甲酸甲酯
• 英文名称: methyl 3-aminoadamantane-1-carboxylate
• 英文别名: methyl 3-amino-1-adamantanecarboxylate
• CAS: 80103-18-0
• 化学式: C₁₂H₁₉NO₂
• 分子量: 209.288
• InChiKey: YCDFPJJVFUVJJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2922499990

反应信息

• 作为反应物：
  描述：

  3-氨基-1-金刚烷羧酸甲酯 在 sodium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 48.0h， 生成 N,N'-bis(3-aminoadamantane-1-carboxylic acid)oxalamide
  参考文献：
  名称：

  Adamantane-retropeptides, new building blocks for molecular channels

  摘要：

  Novel adamantane-oxalamide derivatives, N,N'-bis(1-adamantylglycine methyl ester)oxalamide (meso-1 and rac-1), N,N'-bis(3-aminoadamantane- 1-carboxylic acid methyl ester)oxalamide (2) and N,N'-bis(3-aminoadamantane-1-carboxylic acid)oxalamide (3) were prepared and structurally characterized by spectroscopic methods and X-ray analysis. Crystal packing of the structures meso-1 and rac-1 is defined by one-dimensional alpha-networks of hydrogen-bonded chains. The crystal structures of 2 and 3 are characterized by two-dimensional beta-networks of hydrogen bonds. The oxalamide 3 crystallizes as the solvates only. In the crystal structure of 3 the protic solvent participates in hydrogen bonding with the oxalamide moieties. However, in non-protic solvents 3 crystallizes as a solvate but the solvent does not participate in hydrogen bonding. The two-dimensional network of hydrogen bonds connecting molecules of 3 generates channels, which are filled by discrete solvent molecules. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.066
• 作为产物：
  描述：

  甲醇 、 3-氨基-1-金刚烷甲酸盐酸盐 在 氯化亚砜 作用下， 反应 24.0h， 生成 3-氨基-1-金刚烷羧酸甲酯
  参考文献：
  名称：

  Adamantane-retropeptides, new building blocks for molecular channels

  摘要：

  Novel adamantane-oxalamide derivatives, N,N'-bis(1-adamantylglycine methyl ester)oxalamide (meso-1 and rac-1), N,N'-bis(3-aminoadamantane- 1-carboxylic acid methyl ester)oxalamide (2) and N,N'-bis(3-aminoadamantane-1-carboxylic acid)oxalamide (3) were prepared and structurally characterized by spectroscopic methods and X-ray analysis. Crystal packing of the structures meso-1 and rac-1 is defined by one-dimensional alpha-networks of hydrogen-bonded chains. The crystal structures of 2 and 3 are characterized by two-dimensional beta-networks of hydrogen bonds. The oxalamide 3 crystallizes as the solvates only. In the crystal structure of 3 the protic solvent participates in hydrogen bonding with the oxalamide moieties. However, in non-protic solvents 3 crystallizes as a solvate but the solvent does not participate in hydrogen bonding. The two-dimensional network of hydrogen bonds connecting molecules of 3 generates channels, which are filled by discrete solvent molecules. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.066

文献信息

• ADAMANTYL DIAMIDE DERIVATIVES AND USES OF SAME
  申请人：Jimenenz Hermogenes N.

  公开号：US20100022546A1

  公开（公告）日：2010-01-28

  The present invention provides adamantyl-diamide derivatives of formula (1): wherein R 1 and R 2 are as defined herein, or a pharmaceutically acceptable salt thereof; and pharmaceutical compositions and methods using the same.

  本发明提供了公式（1）的脱氢胆酸二酰胺衍生物：其中R1和R2如本文所定义，或其药用可接受的盐；以及使用相同的药物组合物和方法。
• Antiproliferative and Antiviral Activity of Three Libraries of Adamantane Derivatives
  作者：Nikola Basarić、Margareta Sohora、Nikola Cindro、Kata Mlinarić-Majerski、Erik De Clercq、Jan Balzarini

  DOI：10.1002/ardp.201300345

  日期：2014.5

  Three libraries of adamantane derivatives were synthesized and evaluated for antiviral and antiproliferative activities against a broad variety of DNA and RNA viruses. Whereas none of the compounds exhibit antiviral activity at subtoxic concentrations, antiproliferative activity was found against murine leukemia cells (L1210), human T‐lymphocyte cells (CEM), and cervix carcinoma cells (HeLa) for 4

  合成了三个金刚烷衍生物文库，并评估了针对多种 DNA 和 RNA 病毒的抗病毒和抗增殖活性。虽然这些化合物在亚毒浓度下均不表现出抗病毒活性，但在 4、8 和 10 年中发现对鼠白血病细胞 (L1210)、人 T 淋巴细胞 (CEM) 和宫颈癌细胞 (HeLa) 具有抗增殖活性。
• Enantioselective Desymmetrization of 1,3‐Disubstituted Adamantane Derivatives via Rhodium‐Catalyzed C−H Bond Amination: Access to Optically Active Amino Acids Containing Adamantane Core
  作者：Risa Yasue、Kazuhiro Yoshida

  DOI：10.1002/adsc.202001419

  日期：2021.3.16

  85% ee (e.r.=92.4: 7.6) (>99% ee after recrystallization). The synthetic utility of the enantioenriched products as chiral building blocks was demonstrated by transforming one of them into a dipeptide derivative and a Schiff‐base ligand. The absolute configuration of one of the amino acid derivatives was determined unambiguously by X‐ray single‐crystal structure analysis.

  为了合成含有金刚烷核的旋光氨基酸，研究了通过铑催化的CH键氨基化对金刚烷的对映选择性脱对称。在研究各种条件后，发现Rh 2（S -TCPTTL）4催化了双取代的金刚烷与芳氧基磺酰胺的偶联反应。以提供具有高达85％ee（er = 92.4：7.6）（重结晶后> 99％ee）的所需产品。通过将其中一种转化为二肽衍生物和席夫碱配体，证明了对映体富集产品作为手性结构单元的合成效用。通过X射线单晶结构分析明确确定了一种氨基酸衍生物的绝对构型。
• N-Adamantane-substituted tetrapeptide amides
  申请人：G. D. Searle & Co.

  公开号：US04273704A1

  公开（公告）日：1981-06-16

  N-Adamantane-substituted tetrapeptide amides and the pharmacologically acceptable salts thereof are disclosed herein. These compounds are analogs of enkephalin wherein the methionine or leucine of position 5 has been substituted by an adamantyl amide and the glycine of position 2 has been substituted by various amino acid residues. Optionally the tyrosine of position 1 and the phenylalanine of position 4 may be substituted by various amino acid residues. These compounds exhibit agonist activity at opiate receptor sites and are useful as analgesics.

  本文披露了N-金刚烷取代的四肽酰胺及其药理学上可接受的盐。这些化合物是脑啡肽的类似物，其中第5位的蛋氨酸或亮氨酸被金刚烷酰胺替代，第2位的甘氨酸被各种氨基酸残基替代。选项地，第1位的酪氨酸和第4位的苯丙氨酸可以被各种氨基酸残基替代。这些化合物在鸦片受体位点表现出激动剂活性，并可用作镇痛剂。
• Invention Concerning Aminoadamantane Compounds
  申请人：Schreiner Peter R.

  公开号：US20080275112A1

  公开（公告）日：2008-11-06

  The present invention describes 1-aminoadamantane derivatives and 3-aminoadamantane-1-carboxylic derivatives in which the 5- or 7-position of the basic adamantane structure can be optionally substituted, methods for the production of the compounds based on the present invention, and methods for the coupling of the monomeric 3-aminoadamantane-1-carboxylic derivatives thus obtained to oligomers. The compounds based on the present invention are suitable for the utilisation as antiviral active ingredients, artificial ion channels, as well as for the therapy, diagnostics and prophylaxis of diseases in which a dysfunction of the GABA system occurs.

  本发明描述了1-氨基金刚烷衍生物和3-氨基金刚烷-1-羧酸衍生物，其中基本金刚烷结构的5-或7-位可以选择性地被取代，基于本发明的化合物的制备方法，以及将单体3-氨基金刚烷-1-羧酸衍生物耦合到寡聚体的方法。基于本发明的化合物适用于作为抗病毒活性成分、人工离子通道，以及治疗、诊断和预防GABA系统功能障碍性疾病。