9-吖啶羧酸,1,2,3,4,5,6,7,8-八氢-4,5-二羰基-,乙基酯 | 132844-22-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 9-吖啶羧酸,1,2,3,4,5,6,7,8-八氢-4,5-二羰基-,乙基酯
• 英文名称: 4,5-dioxo-1,2,3,4,5,6,7,8-octahydro-9-acridinecarboxylic acid ethyl ester
• 英文别名: Ethyl 4,5-dioxo-1,2,3,6,7,8-hexahydroacridine-9-carboxylate
• CAS: 132844-22-5
• 化学式: C₁₆H₁₇NO₄
• 分子量: 287.315
• InChiKey: ZPJLOGNNHNFINA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  73.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9-吖啶羧酸,1,2,3,4,5,6,7,8-八氢-4,5-二羰基-,乙基酯 在 ammonium acetate 、 sodium cyanoborohydride 作用下， 以 乙醇 、 水 为溶剂， 生成
  参考文献：
  名称：

  Manipulating the stoichiometry and strength of phosphodiester binding to a bisguanidine cleft in DMSO/water solutions

  摘要：

  A cleft with two aminoimidazoline groups preorganized to form a V-shaped cavity was found to bind dibenzyl phosphate in mixtures of DMSO and water.

  DOI：

  10.1021/jo00028a001
• 作为产物：
  描述：

  Ethyl 4,5-dibenzylidene-1,2,3,6,7,8-hexahydroacridine-9-carboxylate 以48%的产率得到9-吖啶羧酸,1,2,3,4,5,6,7,8-八氢-4,5-二羰基-,乙基酯
  参考文献：
  名称：

  扭曲的聚氮杂c裂，用于环己烷-多元醇的络合

  摘要：

  合成了聚氮杂裂，并显示其在氯仿中结合1,2-和1,3-环己二醇和1,3-2-环己三醇。

  DOI：

  10.1016/s0040-4039(00)88502-0

文献信息

• Bis(alkylguanidinium) receptors for phosphodiesters: effect of counterions, solvent mixtures, and cavity flexibility on complexation
  作者：Diane M. Kneeland、Katsuhiko Ariga、Vincent M. Lynch、Chia Yu Huang、Eric V. Anslyn

  DOI：10.1021/ja00075a021

  日期：1993.11

  Four bis(guanidinium) receptors have been synthesized in which the guanidinium groups are spatially preorganized by an octahydroacridine (meso-3 and d,l-3) or hexahydrodicyclopenta[b,e]pyridine (meso-4 and d,l-4) spacer to complement a phosphodiester. These structures are designed to mimic the active site of staphylococcal nuclease and, thereby, form four hydrogen bonds to a bound phosphodiester with

  已经合成了四种双（胍）受体，其中胍基团在空间上由八氢吖啶（meso-3 和 d,l-3）或六氢二环戊二烯 [b,e] 吡啶（meso-4 和 d,l-4）预先组织间隔以补充磷酸二酯。这些结构旨在模拟葡萄球菌核酸酶的活性位点，从而与结合的磷酸二酯形成四个氢键，而宿主结构几乎没有重组。合成包括两部分：间隔基的构建和通过胺和硫脲盐之间的分子内环化形成氨基咪唑啉基团
• Huang, Chia-Yu; Cabell, Larry A.; Anslyn, Eric V., Journal of the American Chemical Society, 1994, vol. 116, # 7, p. 2778 - 2790
  作者：Huang, Chia-Yu、Cabell, Larry A.、Anslyn, Eric V.

  DOI：——

  日期：——
• Enolate complexation in acetonitrile with a neutral polyaza cleft
  作者：Anne M. Kelly-Rowley、Larry A. Cabell、Eric V. Anslyn

  DOI：10.1021/ja00025a052

  日期：1991.12
• Molecular Recognition of Enolates of Active Methylene Compounds in Acetonitrile. The Interplay between Complementarity and Basicity and the Use of Hydrogen Bonding to Lower Guest pKas
  作者：Anne M. Kelly-Rowley、Vincent M. Lynch、Eric V. Anslyn

  DOI：10.1021/ja00117a013

  日期：1995.3

  A model system for enolase and racemase enzymes was used to explore the extent to which traditional hydrogen bonds can increase carbon acidity. Polyazaclefts 1 and 2 were investigated as receptors for active methylene enolates 10 to 19 in acetonitrile. Receptor 1 was designed to form four hydrogen bonds to the heteroatoms of the enolate guests. The synthesis of the receptors began with the central pyridine ring followed by formation of the peripheral pyrrole rings. Binding constants for 1 with the enolates 10 to 17 in acetonitrile vary from 1.75 x 10(2) to 2.72 x 10(4) M(-1). The nature of both the enolate functionality and the counterion were found to affect the strength of complexation. Molecular mechanics and X-ray analysis of host 1 were used to predict the geometries of the guest-host complexes. Nonaqueous titrations with picric acid were performed on enolates 10 to 17 in order to assess the degree to which complexation was changed by the basicity of the enolate, Complementarity of the guest to host 1 was found to be the dominant factor in enolate binding and not guest basicity. However, a correlation was found to exist between basicity and binding for enolates of the same shape and functionality. Binding by host 1 was found to increase the acidity of 1,3-cyclohexanedione by 1.0 pK(a) unit in acetonitrile. Therefore, traditional hydrogen bonds exert only enough anion stabilization to account for a small fraction of the large pK(a) shifts found for enolase and racemase enzymes. Nevertheless, this acidity increase can be exploited as a means to induce deprotonation of 1,3-cyclohexanedione in the presence of 1.
• HUANG, CHIA-YU;CABELL, LARRY A.;ANSLYN, ERIC V., TETRAHEDRON LETT., 31,(1990) N1, C. 7411-7414
  作者：HUANG, CHIA-YU、CABELL, LARRY A.、ANSLYN, ERIC V.

  DOI：——

  日期：——