(R)-2-chloro-N-(1-(naphthalen-1-yl)ethyl)acetamide | 251103-94-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-2-chloro-N-(1-(naphthalen-1-yl)ethyl)acetamide
• 英文别名: 2-chloro-N-[(R)-1-(1-naphthyl)ethyl]ethanamide；(R)-2-chloro-N-[1-(1-naphthyl)ethyl]acetamide；2-chloro-N-[(1R)-1-naphthalen-1-ylethyl]acetamide
• CAS: 251103-94-3
• 化学式: C₁₄H₁₄ClNO
• 分子量: 247.724
• InChiKey: FACKLPCSVDLOKS-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-2-chloro-N-(1-(naphthalen-1-yl)ethyl)acetamide 在 氢氧化钾 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 42.5h， 生成 10-[(R)-1-(1-naphthyl)ethylcarbamoylmethyl]-1,4,7,10-tetraazacyclododecane-1,4,7-triyltrimethylene(methylphosphinic acid)
  参考文献：
  名称：

  Synthesis, NMR, relaxometry and circularly polarised luminescence studies of macrocyclic monoamidetris(phosphinate) complexes bearing a remote chiral centre

  摘要：

  大环单酰胺三(膦酸酯)配体的镧系配合物在水溶液中部分水合。在酰胺基团中引入手性中心导致形成两个不互变的配合物非对映异构体（α-苯乙基为2∶1，α-1-萘乙基为4∶1）。质子、31P NMR和圆偏振发光研究表明，手性碳中心的构型决定了侧臂的螺旋排列和大环环构象，磷中心偏好RRR或SSS构型。

  DOI：

  10.1039/a708667i
• 作为产物：
  描述：

  氯碘甲烷 、 (R)-(-)-1-萘乙基异氰酸酯 在 methyllithium lithium bromide 作用下， 以 乙醚 为溶剂， 以97%的产率得到(R)-2-chloro-N-(1-(naphthalen-1-yl)ethyl)acetamide
  参考文献：
  名称：

  将锂类胡萝卜素加到异氰酸酯中：直接获得合成上有用的N-取代的2-卤代乙酰胺。

  摘要：

  向异氰酸酯中添加类胡萝卜酸锂可提供N-取代的2-卤代乙酰胺的通用途径：该反应可耐受氮原子上存在各种官能化的取代基，包括空间上需要的取代基和反应性卤素。在光学活性异氰酸酯的情况下，未观察到对映体纯度的侵蚀。所制备的底物之一已用于格氏试剂的Charette型化学选择性添加中，从而获得α-氯酮。

  DOI：

  10.1039/c3cc44255a

文献信息

• Synthesis of luminescent homo-dinuclear cationic lanthanide cyclen complexes bearing amide pendant arms through the use of copper catalysed (1,3-Huisgen, CuAAC) click chemistry
  作者：Jennifer K. Molloy、Oxana Kotova、Robert D. Peacock、Thorfinnur Gunnlaugsson

  DOI：10.1039/c1ob06203d

  日期：——

  N-dimethyl acetamide complexes, 2Eu and 2Tb, and for the homo-Eu(III) chiral N-methylnaphthalene based complexes 3Eu (S,S,S) and 4Eu (R,R,R), the formation of the Eu(III) complex of the primary amide analogue of 2, namely 1Eu, was not successful, clearly demonstrating the effect that the nature of the pendant arms has on this reaction. Furthermore, the click reactions between the free alkyne cyclen bis-derivatives

  描述了具有七唑基桥的二核-镧系元素配合物的设计与合成，该配合物是通过在七齿炔炔官能化的环cycle或or配合物与二叠氮化物之间进行铜催化的1,3-环加成反应而形成的（CuAAC反应）。虽然此点击反应对于均一Eu（III）和Tb（III）双三臂旋光子的形成非常有效N，N-二甲基乙酰胺配合物2Eu和2Tb，以及基于均Eu（III）手性N-甲基萘的配合物3Eu（S，S，S）和4Eu（R，R，R），形成的Eu（III）配合物。的伯酰胺类似物2，即1EU，未成功，这清楚地表明，该侧挂臂的性质对本反应的影响。此外，游离炔炔环素双衍生物之间的点击反应（5–8）和二叠氮化物均未成功，最有可能是由于cycln大环对Cu（II）的高亲和力所致。在甲醇溶液中激发三唑或萘触角后，由2–4和2Tb组成的Eu（III）络合物均引起敏化的金属离子中心发射，并确定了它们的水合状态，这表明Eu（III）单核络合物的q约为2
• Strong exciton coupling and circularly polarised luminescence in rigid complexes of chiral macrocyclic tetranaphthylamides
  作者：Rachel S. Dickins、Judith A. K. Howard、Janet M. Moloney、David Parker、Robert D. Peacock、Giuliano Siligardi

  DOI：10.1039/a703182c

  日期：——

  Strong exciton coupling occurs between adjacent pairs of naphthyl chromophores in the chiral sodium and europium complexes of L 1 ; in the constitutionally isomeric complexes of L 2 , intramolecular excimer formation is observed and both sets of Eu complexes give a well defined, metal-based circularly polarised emission.

  在 L 1 的手性钠络合物和铕络合物中，相邻的一对萘基发色团之间发生了强烈的激子耦合；在 L 2 的同分异构体络合物中，观察到了分子内准分子的形成，两组铕络合物都发出了明确的、基于金属的圆极化发射。
• Homologation of Isocyanates with Lithium Carbenoids: A Straightforward Access to α-Halomethyl- and α,α-Dihalomethylamides
  作者：Vittorio Pace、Laura Castoldi、Ashenafi Mamuye、Wolfgang Holzer

  DOI：10.1055/s-0034-1379209

  日期：——

  Treatment of widely available isocyanates with monohalolithium and dihalolithium carbenoids provides a valuable protocol for the one-pot preparation of -halo- and ,-dihaloacetamide derivatives. While monohalolithium carbenoids can be prepared by a smooth lithium-halogen exchange, the preparation of the corresponding dihalo compounds proved to be highly dependent on the base used to realize the deprotonation, with lithium 2,2,6,6-tetramethylpiperidine emerging as optimal. The clear advantages of the procedure are: (a) broad scope of isocyanates that can be employed; (b) preservation of the optical purity when chiral materials are used; (c) divergent access to different haloamides by simply selecting the homologating agents. We also report an application of Charette's imidoyl triflate activation of a secondary amide to the synthesis of an -chloro ketone and N-15 NMR data for selected compounds.
• New fatty acid oxidation inhibitors with increased potency lacking adverse metabolic and electrophysiological properties
  作者：Dmitry O. Koltun、Timothy A. Marquart、Kevin D. Shenk、Elfatih Elzein、Yuan Li、Marie Nguyen、Suresh Kerwar、Dewan Zeng、Nancy Chu、Daniel Soohoo、Jia Hao、Victoria Y. Maydanik、David A. Lustig、Khing-Jow Ng、Heather Fraser、Jeffery A. Zablocki

  DOI：10.1016/j.bmcl.2003.09.093

  日期：2004.1

  New inhibitors of palmitoylCoA oxidation were synthesized based on a structurally novel lead, CVT-3501 (1). Investigation of structure-activity relationships was conducted with respect to potency of inhibition of cardiac mitochondrial palmitoylCoA oxidation and metabolic stability. Potent and metabolically stable analogues 33, 42, and 43 were evaluated in vitro for cytochrome P450 inhibition and potentially adverse electrophysiological effects. Compound 33 was also found to have favorable pharmacokinetic properties in rat. (C) 2003 Elsevier Ltd. All rights reserved.
• Fluorescent PET chemosensors for lithium
  作者：Thorfinnur Gunnlaugsson、Bastien Bichell、Claire Nolan

  DOI：10.1016/j.tet.2004.04.082

  日期：2004.6

  The synthesis of the chiral diaza-9-crown-3 derivatives 1 (S,S) and 2 (R,R) is described. These sensors were designed as luminescent chemosensors for lithium where the fluorescence emission from the naphthalene moieties was 'switched on' upon Li+ recognition by the crown ether moiety in organic solvents, showing excellent selectivity over other group I and group II cations. Even though the recognition of Li+ was not achieved in water (pH 7.4) or aqueous alcohol solution, the fluorescence (which was switched on at pH 7.4) was substantially modulated by spherical anions, where the fluorescence emission was quenched in the presence of Br- and I- but less by Cl- and not by acetate. This indicates that the emission was quenched by heavy-atom affect. The recognition of Li+ was also investigated by H-1 NMR in CD3CN and by observing the changes in the circular dicromism spectra. For the former, the resonances for the crown ether moiety and alpha-methyl protons adjacent to the ring were sifted upfield and broadened, whereas for 1 the intensity of the CD signal for the pi-pi transition was substantially modulated upon Li+ recognition. (C) 2004 Elsevier Ltd. All rights reserved.