2-(1-adamantanyl)-N-benzyl-ethanamide | 286386-48-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(1-adamantanyl)-N-benzyl-ethanamide
• 英文别名: 2-(1-adamantanyl)-N-benzylethanamide；2-(1-adamantyl)-N-benzylacetamide
• CAS: 286386-48-9
• 化学式: C₁₉H₂₅NO
• mdl: MFCD01790112
• 分子量: 283.414
• InChiKey: YQBDBDHKAYEANT-UHFFFAOYSA-N

物化性质

• 溶解度：
  0.6 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.631
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-金刚烷乙酸 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 potassium carbonate 、 Selectfluor 作用下， 以 乙腈 为溶剂， 反应 16.0h， 生成 2-(1-adamantanyl)-N-benzyl-ethanamide
  参考文献：
  名称：

  通过亲电氟化试剂 Selectfluor，元素硫介导的羧酸向酰氟的转化

  摘要：

  使用 Selectfluor 实现元素硫介导的从羧酸合成酰基氟。广泛的酰氟可从羧酸中获得，同时避免形成酸酐。19 F NMR谱表明原位生成的S 8 -氟硫阳离子A和中性S 8 -二氟化物A'是该脱氧氟化反应中的活性物质。

  DOI：

  10.1021/acs.orglett.3c00701

文献信息

• All Non‐Carbon B ₃ NO ₂ Exotic Heterocycles: Synthesis, Dynamics, and Catalysis
  作者：Christopher R. Opie、Hidetoshi Noda、Masakatsu Shibasaki、Naoya Kumagai

  DOI：10.1002/chem.201900715

  日期：2019.3.27

  The B3NO2 six‐membered heterocycle (1,3‐dioxa‐5‐aza‐2,4,6‐triborinane=DATB), comprising three different non‐carbon period 2 elements, has been recently demonstrated to be a powerful catalyst for dehydrative condensation of carboxylic acids and amines. The tedious synthesis of DATB, however, has significantly diminished its utility as a catalyst, and thus the inherent chemical properties of the ring

  B 3 NO 2六元杂环（1,3-二氧杂-5-氮杂-2,4,6-三硼烷= DATB），由三种不同的非碳2期元素组成，最近被证明是羧酸脱水缩合的强大催化剂酸和胺。然而，繁琐的DATB合成大大降低了其作为催化剂的用途，因此，实际上仍未探索环系统的固有化学性质。在此公开了一种通用且简便的合成策略，该策略利用含嘧啶的支架可靠地安装硼原子，从而以模块化的方式由廉价材料制成了一系列Pym-DATB。可溶性Pym‐DATB衍生物的鉴定可用于研究B 3 NO 2的动力学性质环系统，根据介质的不同，显示出不同的开环和开环行为。易于获取的Pym‐DATB证明了其作为脱水酰胺化的有效催化剂的实用性，具有广泛的底物范围和官能团耐受性，为试剂驱动的酰胺化提供了一种通用且实用的催化替代方法。
• Cavitand−Porphyrins
  作者：Stephen D. Starnes、Dmitry M. Rudkevich、Julius Rebek

  DOI：10.1021/ja010038r

  日期：2001.5.1

  The synthesis and characterization of new nanoscale container molecules 7 and 8 are described. They are covalent hybrids of deepened, self-folding cavitands and metalloporphyrins. In receptor 7, the Zn-porphyrin wall is directly built onto the cavitand skeleton. Host 8 features a large unimolecular cavity containing two cavitands attached with the Zn-porphyrin wall. Its dimensions, similar to 10 x 25 Angstrom, place it among the largest synthetic hosts prepared to date. A series of adamantyl- and pyridyl-containing guests 14-20 of various lengths were prepared and used to determine the hosts' binding abilities in solution using UV/vis and H-1 NMR spectroscopy. Intramolecular hydrogen bonds at the upper rims of the cavitands resist the unfolding of the inner cavities and thereby increase the energetic barrier to guest exchange. The exchange is slow on the NMR time scale (at less than or equal to 300 K), and kinetically stable complexes result. When the cavities and metalloporphyrins participate simultaneously in the binding event, very high affinities for guests are found (-DeltaG(295) up to 10 kcal mol(-1) in toluene), to which the porphyrin fragments contribute significantly (-DeltaG(295) up to 6 kcal mol(-1)). The pairwise selection of two different guests by molecular container 8 is reported, and the termolecular complex formed raises the possibility of metal-catalyzed bimolecular reactions in these containers.