methyl 5-((tert-butoxycarbonyl)amino)pentanoate | 85908-97-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 5-((tert-butoxycarbonyl)amino)pentanoate
• 英文别名: 5-[[(1,1-dimethylethoxy)carbonyl]amino]Pentanoic acid methyl ester；methyl 5-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate
• CAS: 85908-97-0
• 化学式: C₁₁H₂₁NO₄
• mdl: MFCD24393255
• 分子量: 231.292
• InChiKey: GVROIRXPCGJMQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.818
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 5-((tert-butoxycarbonyl)amino)pentanoate 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 17.0h， 以95%的产率得到5-[[(1,1-Dimethylethoxy)carbonyl]amino]pentanoic acid hydrazide
  参考文献：
  名称：

  [EN] 1,3,4-OXADIAZOLE AND 1,3,4-THIADIAZOLE &bgr;-LACTAMASE INHIBITORS
  [FR] INHIBITEURS DE LA 1,3,4-OXADIAZOLE ET DE LA 1,3,4-THIADIAZOLE BÊTA-LACTAMASE

  摘要：

  公开号：

  WO2013149121A8
• 作为产物：
  描述：

  碳酸二叔丁酯 在 sodium hydroxide 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 生成 methyl 5-((tert-butoxycarbonyl)amino)pentanoate
  参考文献：
  名称：

  Asymmetric catalysis of intramolecular N–H insertion reactions of α-diazocarbonyls

  摘要：

  Intramolecular N-H insertion reactions of alpha-diazocarbonyl substrates are catalysed by rhodium(II) carboxylates with catalyst-dependent competition with C-H insertion and beta-elimination; asymmetric N-H insertion leading to a pipecolic acid derivative with ee up to 45% is achieved using chiral catalysts.

  DOI：

  10.1039/cc9960001465

文献信息

• Two-way homologation of aliphatic aldehydes: Both one-carbon shortening and lengthening via the same intermediate
  作者：Jae Won Yoo、Youngran Seo、Jong Beom Park、Young Gyu Kim

  DOI：10.1016/j.tet.2019.130883

  日期：2020.2

  Aliphatic aldehydes can be homologated to both one-carbon shorter and one-carbon longer homologous carbonyl compounds through the 2–4 steps of reactions via the same intermediates, β,γ-unsaturated α-nitrosulfones, prepared from the proline-catalyzed sequential reactions of several aliphatic aldehydes with phenylsulfonylnitromethane. While the oxidative cleavage of the key intermediates gave one-carbon

  脂肪醛可通过相同的中间体β，γ-不饱和α-硝基砜，经脯氨酸催化的连续反应制备的相同中间体，通过2–4个反应，与一碳短和一碳长的同源羰基化合物同源。几种脂肪醛与苯磺酰基硝基甲烷。当关键中间体的氧化裂解得到一碳较少的同源羰基化合物时，相同关键中间体的还原随后被氧化产生了更多一碳的同源羰基化合物。
• Novel Labelled Cannabinergic Ligands and Related Analogs
  申请人：Makriyannis Alexandros

  公开号：US20210300937A1

  公开（公告）日：2021-09-30

  Novel cannabinoid ligands represented by the general formulas I, II, and III and methods for preparation and use within which one or more of a fluorescent ligand, nitroxide spin label, metal chelate, biotin moiety, or group with enhanced polarity may be incorporated. The compounds can bind to and modulate the cannabinoid CB1 and CB2 receptors and thereby considered specific ligands for these receptors. Some of the disclosed compounds that bind to cannabinoid CB1 and CB2 receptors can exhibit tight or irreversible binding characteristics for these receptors. Due to the presence of the imaging/diagnostic and/or therapeutic functional groups including fluorescent groups, nitroxide spin labels, metal chelates, biotin moieties, and groups with enhanced polarity, the disclosed compounds may be useful as imaging/diagnostic tools and/or therapeutic agents.

  新型大麻素配体由一般公式I、II和III表示，以及用于制备和使用的方法，其中可以包含一个或多个荧光配体、亚硝基自旋标记、金属螯合物、生物素基团或具有增强极性的基团。这些化合物可以结合并调节大麻素CB1和CB2受体，因此被认为是这些受体的特异性配体。一些公开的结合到大麻素CB1和CB2受体的化合物可能表现出对这些受体的紧密或不可逆结合特性。由于含有成像/诊断和/或治疗功能基团，包括荧光基团、亚硝基自旋标记、金属螯合物、生物素基团和具有增强极性的基团，公开的这些化合物可能作为成像/诊断工具和/或治疗剂而有用。
• Insertion of Methylene Units into the Turn Segment of Designed β-Hairpin Peptides
  作者：S. C. Shankaramma、S. Kumar Singh、Aruna Sathyamurthy、P. Balaram

  DOI：10.1021/ja990412b

  日期：1999.6.1

  loop. Backbone proton chemical shifts, vicinal coupling constants, and circular dichroism spectra for the two peptides are virtually indistinguishable. Nuclear Overhauser effects corresponding to short cross-strand interproton distances confirm that the registry of the beta-hairpin structure is maintained in the delta-Ava peptide. Restrained molecular dynamics simulations, using experimental constraints

  已在模型序列 Boc-Leu-Val-Val-Dpro-delta-Ava-Leu-Val-Val-OMe 中研究了亚甲基插入 β-发夹肽的转折段的影响。该序列与先前充分表征的模型 β-发夹八肽 Boc-Leu-Val-Val-DPro-Gly-Leu-Val-Val-OMe 相关。用 delta-Ava（delta-氨基戊酸）替代 Gly 形式上对应于转角段从两个残基环到三残基环的扩展。两种肽的骨架质子化学位移、邻位耦合常数和圆二色光谱几乎无法区分。与短跨链质子间距离相对应的核 Overhauser 效应证实，β-发夹结构的注册表保持在 delta-Ava 肽中。受限分子动力学模拟，使用实验约束，产生两个与 NOE 数据一致的结构族。这两个家族都对应于 β-发夹构象，仅在 delta-Ava 残基的骨架扭转角上有所不同。
• Ruthenium tetroxide oxidation of cyclic N-acylamines by a single layer method: formation of ω-amino acids
  作者：Mamoru Kaname、Shigeyuki Yoshifuji、Haruki Sashida

  DOI：10.1016/j.tetlet.2008.02.127

  日期：2008.4

  The ruthenium tetroxide oxidation of cyclic N-acyl amines by a 10% NaIO4 aqueous solution containing tert-butanol as a single layer system resulted in the endo-cyclic C–N bond cleavage to afford the ω-amino acids as almost sole products in good yields, while a similar oxidation under the double layer using a NaIO4 aqueous solution, and ethyl acetate gave the N-acyl lactams.

  含叔丁醇作为单层系统的10％NaIO 4水溶液对环N-酰基胺的四氧化钌氧化导致环内C-N键断裂，从而提供ω-氨基酸，几乎是唯一的产物。良好的收率，同时使用NaIO 4水溶液和乙酸乙酯在双层下进行类似的氧化，得到N-酰基内酰胺。
• One‐Step Synthesis of the 1‐Azaspiro[5.5]undecane Skeleton Characteristic of Histrionicotoxin Alkaloids from Linear Substrates via Hg(OTf) ₂ ‐Catalyzed Cycloisomerization
  作者：Kunihiro Matsumura、Keisuke Nishikawa、Hiroaki Yoshida、Toshiki Niwa、Yuichiro Fushii、Matsumi Doe、Yoshiki Morimoto

  DOI：10.1002/asia.202100383

  日期：2021.7.19

  possess a unique structure characterized by a 1-azaspiro[5.5]undecane skeleton common to the HTX family. The unique molecular architecture of HTXs and the interest as potential target drugs have prompted synthetic chemists to promote the total synthesis so far. However, all of the synthetic strategies to access the 1-azaspiro[5.5]undecane framework of HTXs take a multistep approach from linear starting

  从毒箭蛙中分离出的组氨酸毒素 (HTX) 生物碱具有独特的结构，其特征是 HTX 家族共有的 1-azaspiro[5.5] 十一烷骨架。HTXs 独特的分子结构和作为潜在靶点药物的兴趣促使合成化学家迄今为止促进全合成。然而，由于六元碳环或氮杂环的逐步构建，所有获得 HTX 的 1-氮杂螺[5.5]十一烷骨架的合成策略都采用线性起始材料的多步方法。在此，我们报告了利用我们的三氟甲磺酸汞 (Hg(OTf) 2 )从带有N-甲氧基羰基的线性氨基炔酮底物直接一步构建 1-氮杂螺[5.5]十一烷骨架)-催化的环异构化反应。分别从氮杂螺环合成 HTX-235A 和 HTX-283A，证明了这种新方法的实用性。