7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]heptane-2-carboxylic acid | 711082-67-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]heptane-2-carboxylic acid
• 英文别名: endo-7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]heptane-2-carboxylic acid；(1R,2R,4S)-7-[(tert-Butoxy)carbonyl]-7-azabicyclo[2.2.1]heptane-2-carboxylic acid；(1R,2R,4S)-7-[(2-methylpropan-2-yl)oxycarbonyl]-7-azabicyclo[2.2.1]heptane-2-carboxylic acid
• CAS: 711082-67-6
• 化学式: C₁₂H₁₉NO₄
• 分子量: 241.287
• InChiKey: XRDRXGVDCVQVPV-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]heptane-2-carboxylic acid 在 4-二甲氨基吡啶 、 lithium hydroxide 、 草酰氯 、 sodium hydride 、 sodium carbonate 、 N,N-二甲基甲酰胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 56.0h， 生成 (1S,2S,4R)-7-azabicyclo[2.2.1]heptane-2,7-dicarboxylic acid 2-benzyl ester 7-(9H-fluoren-9-ylmethyl) ester
  参考文献：
  名称：

  Oligomers of β-amino acid bearing non-planar amides form ordered structures

  摘要：

  In this report, we explore the feasibility of using bicyclic chiral beta-amino acids, (1R,2R,4S)- and (1S,2S,4R)-7-azabicyclo[2.2.1]-heptane-2-carboxylic acid (R-Ah2c and S-Ah2c, respectively), to prepare novel peptides with unique properties. Facile cis-trans isomerization of the non-planar amide bonds of these beta-amino acids should result in great flexibility of the backbone structure of beta-peptides containing them. Indeed, oligomers of these amino acids showed thermostability and characteristic CD absorptions, which were not concentration-dependent, suggesting that the oligomers remained monomeric. The results indicated the formation of self-organized monomeric structures with chain-length-dependent stabilization. Energy calculations suggested that the peptides can take helical structures in which the energy barriers to cis-trans isomerization are greater for the central amide bonds than for the terminal amides. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.062
• 作为产物：
  描述：

  (1S,4R)-7-叔-丁基2-甲基3-溴-7-氮杂二环[2.2.1]庚-2,5-二烯-2,7-二甲酸基酯 在 palladium on activated charcoal lithium hydroxide 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 15.0h， 生成 7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]heptane-2-carboxylic acid
  参考文献：
  名称：

  Oligomers of β-amino acid bearing non-planar amides form ordered structures

  摘要：

  In this report, we explore the feasibility of using bicyclic chiral beta-amino acids, (1R,2R,4S)- and (1S,2S,4R)-7-azabicyclo[2.2.1]-heptane-2-carboxylic acid (R-Ah2c and S-Ah2c, respectively), to prepare novel peptides with unique properties. Facile cis-trans isomerization of the non-planar amide bonds of these beta-amino acids should result in great flexibility of the backbone structure of beta-peptides containing them. Indeed, oligomers of these amino acids showed thermostability and characteristic CD absorptions, which were not concentration-dependent, suggesting that the oligomers remained monomeric. The results indicated the formation of self-organized monomeric structures with chain-length-dependent stabilization. Energy calculations suggested that the peptides can take helical structures in which the energy barriers to cis-trans isomerization are greater for the central amide bonds than for the terminal amides. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.062

文献信息

• Visible-Light-Triggered Release of Nitric Oxide from N-Pyramidal Nitrosamines
  作者：Fumika Karaki、Yoji Kabasawa、Takahiro Yanagimoto、Nobuhiro Umeda、Firman、Yasuteru Urano、Tetsuo Nagano、Yuko Otani、Tomohiko Ohwada

  DOI：10.1002/chem.201101427

  日期：2012.1.23

  many organic/inorganic compounds that release nitric oxide (NO) upon photoirradiation (phototriggered caged‐NOs) have been reported, their photoabsorption wavelengths mostly lie in the UV region, because XNO bonds (X=heteroatom and metal) generally have rather strong π‐bond character. Thus, it is intrinsically difficult to generate organic compounds that release NO under visible light irradiation. Herein

  虽然（phototriggered笼-NOS）已经被报道，释放一氧化氮（NO）在光照射许多有机/无机化合物，它们的光吸收波长大多位于紫外区，因为X  NO键（X =杂原子和金属）通常具有相当强大的π键性格。因此，本质上难以产生在可见光照射下释放NO的有机化合物。在此，描述了在可见光照射下释放NO的7-氮杂双环[2.2.1]庚烷的N-锥体亚硝胺衍生物的结构和性质。这些亚硝胺的吸收的红移，这归因于HOMO（N）-LUMO（π*）与N的非平面结构相关联的过渡NO部分使分子能够吸收可见光，从而导致NNO键断裂。因此，这些化合物是先天性有机笼状NO，不会被可见光束缚。
• [EN] BICYCLIC HETEROCYCLE DERIVATIVES AND METHODS OF USE THEREOF<br/>[FR] DÉRIVÉS D'HÉTÉROCYCLES BICYCLIQUES ET LEURS PROCÉDÉS D'UTILISATION
  申请人：SCHERING CORP

  公开号：WO2010075273A1

  公开（公告）日：2010-07-01

  The present invention relates to Bicyclic Heterocycle Derivatives, compositions comprising a Bicyclic Heterocycle Derivative, and methods of using the Bicyclic Heterocycle Derivatives for treating or preventing obesity, diabetes, a metabolic disorder, a cardiovascular disease or a disorder related to the activity of a GPCR in a patient.

  本发明涉及双环杂环衍生物，包含双环杂环衍生物的组合物，以及使用双环杂环衍生物治疗或预防患者的肥胖、糖尿病、代谢紊乱、心血管疾病或与GPCR活性相关的疾病的方法。
• Structure–activity relationships of adenosines with heterocyclic N6-substituents
  作者：T.D. Ashton、Kylee M. Aumann、Stephen P. Baker、Carl H. Schiesser、Peter J. Scammells

  DOI：10.1016/j.bmcl.2007.10.028

  日期：2007.12

  Two series of N-6-substituted adenosines with monocyclic and bicyclic N-6 substituents containing a heteroatom were synthesized in good yields. These derivatives were assessed for their affinity ([H-3]CPX), potency, and intrinsic activity (cAMP accumulation) at the A, adenosine receptor in DDT1 MF-2 cells. In the monocyclic series, the N-6-tetrahydrofuran-3-yl and thiolan-3-yl adenosines (1 and 26, respectively) were found to possess similar activities, whereas the corresponding selenium analogue 27 was found to be more potent. A series of nitrogen containing analogues showed varying properties, N-6-((3R)-1-benzyloxycarbonylpyrrolidin-3-yl)adenosine (30) was the most potent at the AIAR; IC50 = 3.2 nM. In the bicyclic series, the effect of a 7-azabicyclo[2.2.1]heptan-2-yl substituent in the N-6-position was explored. N6- (7-Azabicyclo[2.2.1] heptan-2-yl)adeno sine (38) proved to be a reasonably potent A, agonist (K-i = 51 nM, IC50 = 35 nM) while further substitution on the 7 ''-nitrogen with tert-butoxycarbonyl (31, IC50 = 2.5 nM) and 2-bromobenzyloxycarbonyl (34, IC50 = 9.0 nM) gave highly potent A(1)AR agonists. (c) 2007 Elsevier Ltd. All rights reserved.