(2,3,4,5,6-Pentafluorophenyl) 6-acetyloxynaphthalene-2-carboxylate | 166539-78-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2,3,4,5,6-Pentafluorophenyl) 6-acetyloxynaphthalene-2-carboxylate
• CAS: 166539-78-2
• 化学式: C₁₉H₉F₅O₄
• 分子量: 396.27
• InChiKey: MVWITZOPZSYZGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  5-氨基-5-脱氧-2,3-O-(1-甲基亚乙基)-腺苷酸 、 (2,3,4,5,6-Pentafluorophenyl) 6-acetyloxynaphthalene-2-carboxylate 在 三乙胺 作用下， 以 氘代氯仿 为溶剂， 生成 [6-[[(3aR,4R,6R,6aR)-4-(6-aminopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methylcarbamoyl]naphthalen-2-yl] acetate
  参考文献：
  名称：

  Rebek 自我复制系统的动力学分析：是否存在争议？

  摘要：

  1 和 2 的 Rebek 自复制反应，由两种反应物与所得产物 3 络合催化（Tjivikua, T.；等人 J. Am. Chem. Soc. 1990, 112, 1249-1250. Nowick, JS ; et al. J. Am. Chem. Soc. 1991, 113, 8831-8839. Wintner, EA; et al. Acc. Chem. Res. 1994, 27, 198-203. Conn, MM; et al. J. Am. Chem. Soc. 1994, 116, 8823-8824)，以及 Menger 等人的相关工作。(Menger, FM; et al. J. Am. Chem. Soc. 1994, 116, 3613-3614. Menger, FM; et al. J. Org. Chem. 1995, 60, 2870-2878) 已

  DOI：

  10.1021/ja960324g
• 作为产物：
  描述：

  五氟苯酚 、 6-acetoxy-2-naphthalenecarboxylic acid chloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以77.4%的产率得到(2,3,4,5,6-Pentafluorophenyl) 6-acetyloxynaphthalene-2-carboxylate
  参考文献：
  名称：

  Evidence for an Alternative Mechanism to a Previously Proposed Self-Replicating System

  摘要：

  Rebek et al.(1,2) have proposed a ''self-replicative'' mechanism in which the amide product of an ester aminolysis forms a termolecular complex with the ester and amine reactants. In this manner, the product catalyzes its own formation. The evidence for the mechanism lies mainly in a 40-70% acceleration when product is added externally to the reaction mixture. The system has now been reinvestigated owing, in part, to doubts created by troublesome experimental problems (e.g. small rate enhancements coupled to greater than or equal to 35% unidentified side reactions) and by the entropic unlikelihood of the highly constrained termolecular complex. Our new experiments prove that the Rebek mechanism is unnecessary. Thus, the aminolysis of simple naphthoyl and benzoyl esters, both lacking any hydrogen-bonding sites, are catalyzed by the Rebek ''template''. In the latter case, the reactions were run under the identical conditions used recently by Rebek (2 mM) while monitoring the formation of the major reaction product. Although the benzoyl ester cannot hydrogen-bond to the template, the ester aminolysis is catalyzed by the template to an extent even greater than that observed by Rebek (i.e. 2-fold). The Rebek mechanism, predicated upon ester/template binding, is clearly invalidated by these experiments. An alternative mechanism, involving amide catalysis, is proposed and found consistent with all available data.

  DOI：

  10.1021/jo00114a043