N-phthaloyl-α-aminoadipic acid | 137407-92-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: N-phthaloyl-α-aminoadipic acid
• 英文别名: NSC 348926；2-phthalimido-hexanedioic acid；2-Phthalimido-adipinsaeure；2-Phthalimidoadipic acid；2-(1,3-dioxoisoindol-2-yl)hexanedioic acid
• CAS: 137407-92-2
• 化学式: C₁₄H₁₃NO₆
• 分子量: 291.26
• InChiKey: WJNORNDVKYKEGX-UHFFFAOYSA-N

物化性质

• 熔点：
  224-226 °C(Solv: water (7732-18-5))
• 沸点：
  541.9±40.0 °C(Predicted)
• 密度：
  1.505±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-phthaloyl-α-aminoadipic acid 在 dimethyl sulfide borane 、 sodium sulfate 、 三乙胺 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Synthesis and antibacterial evaluation of phosphonic acid analogues of diaminopimelic acid

  摘要：

  Diaminopimelic acid is an essential amino acid in the peptidoglycan of Gram-negative bacteria, mycobacteria and some Gram-positive bacteria. It can be used as a target for the development of antibacterial agents. In this article the synthesis of a series of phosphonic acid analogues of this diamino-dicarboxylic acid is described: mono- and diphosphonic acid derivatives as well as their homologues, N-alkyl analogues and some peptidyl derivatives. A phenylphosphinic derivative was also prepared. All the prepared compounds were tested for their antibacterial activity against a series of Gram-positive, Gram-negative and mycobacteria. They were also tested as possible inhibitors of the UDP-MurNAc-L-Ala-gamma-D-Glu: meso-DAP synthetase. No significant biological activity was found.

  DOI：

  10.1016/0223-5234(91)90146-e
• 作为产物：
  描述：

  6-hydroxy-2-phthalimido-hexanoic acid 在 sodium hydroxide 、 potassium permanganate 、 水 作用下， 生成 N-phthaloyl-α-aminoadipic acid
  参考文献：
  名称：

  Gaudry, Canadian Journal of Research, Section B: Chemical Sciences, 1949, vol. 27, p. 21,23

  摘要：

  DOI：

文献信息

• Catalyst-controlled site-selective methylene C–H lactonization of dicarboxylic acids
  作者：Hau Sun Sam Chan、Ji-Min Yang、Jin-Quan Yu

  DOI：10.1126/science.abq3048

  日期：2022.6.24

  and γ-methylene carbon-hydrogen (C-H) bonds of free carboxylic acids is a long-standing challenge. Here we show that, with a pair of palladium catalysts assembled with quinoline-pyridone ligands of different chelate ring sizes, it is possible to perform highly site-selective monolactonization reactions with a wide range of dicarboxylic acids, generating structurally diverse and synthetically useful γ-

  游离羧酸的β-和γ-亚甲基碳氢（CH）键的催化剂控制的位点选择性活化是一个长期存在的挑战。在这里，我们表明，通过一对由不同螯合环尺寸的喹啉-吡啶酮配体组装的钯催化剂，可以与多种二羧酸进行高度位点选择性的单内酯化反应，产生结构多样且合成上有用的γ-和δ-内酯通过位点选择性β-或γ-亚甲基CH活化。剩余的羧基可作为进一步合成应用的多功能关键，如从丰富的二羧酸中全合成两种天然产物 myrotheciumone A 和pedicellosine 所证明的那样。
• Shcherbakov, V. I.; Ivanov, E. F.; Khorshev, S. Ya., Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 1991, vol. 21, p. 1549 - 1568
  作者：Shcherbakov, V. I.、Ivanov, E. F.、Khorshev, S. Ya.、Feldman, M. S.、Kopytov, E. B.、Konkina, T. N.

  DOI：——

  日期：——
• Oxidation of organic compounds by zinc permanganate
  作者：Saul Wolfe、Christopher F. Ingold

  DOI：10.1021/ja00364a054

  日期：1983.12
• Synthesis of stereoisomers of 2,4-diaminoglutaric and 2,5-diaminoadipic acids
  作者：V. P. Krasnov、E. A. Zhdanova、M. A. Korolyova、I. M. Bukrina、M. I. Kodess、V. Kh. Kravtsov、V. N. Biyushkin

  DOI：10.1007/bf02494371

  日期：1997.2

  Stereoisomers of 2,4-diaminoglutaric and 2,5-diaminoadipic acids were synthesized from glutamic and 2-aminoadipic acids, respectively. The stereochemistry of the products was established by IH NMR spectroscopy and X-ray analysis.
• WOLFE, S.;INGOLD, CH. F., J. AMER. CHEM. SOC., 1983, 105, N 26, 7755-7757
  作者：WOLFE, S.、INGOLD, CH. F.

  DOI：——

  日期：——