methyl 6-bromo-5-oxo-2-phthalimidohexanoate | 150716-13-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 6-bromo-5-oxo-2-phthalimidohexanoate
• 英文别名: methyl 6-bromo-2-(1,3-dioxo-1,3-dihydro-1H-isoindol-2-yl)-5-oxohexanoate；Methyl 6-bromo-2-(1,3-dioxoisoindol-2-yl)-5-oxohexanoate
• CAS: 150716-13-5
• 化学式: C₁₅H₁₄BrNO₅
• 分子量: 368.184
• InChiKey: XQAKSCLKSDDRGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  80.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 6-bromo-5-oxo-2-phthalimidohexanoate 在 sodium hydride 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 12.5h， 生成 methyl 6-(dimethyl-λ4-sulfanylidene)-2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)-5-oxohexanoate
  参考文献：
  名称：

  硫叶立德 13. 酮稳定硫叶立德的合成与分子内环化

  摘要：

  从 N-邻苯二甲酰谷氨酸中获得了酮稳定的硫单和双硫醚，并研究了它们的分子内环化。在α-羧基上得到的叶立德分子内环化得到吡咯里西啶二酮结构的产物；作为中间体双卡宾分子内重组的结果，双酰化物产生了环庚烯衍生物。在 γ-羧基上得到的叶立德没有进行环化，得到甲硫酮和氧代苯甲酸酯。

  DOI：

  10.1007/s11172-006-0202-6
• 作为产物：
  描述：

  N-phthaloyl glutamic acid α-methyl ester 在 氯化亚砜 、 氢溴酸 作用下， 以 四氢呋喃 、 乙醚 、 溶剂黄146 为溶剂， 反应 3.5h， 生成 methyl 6-bromo-5-oxo-2-phthalimidohexanoate
  参考文献：
  名称：

  Synthesis and antitrypanosomal evaluation of some thiazole-containing amino acids and peptides

  摘要：

  Several amino acids and peptides containing thiazole and thiazolidine residues were prepared. They were tested in vivo and in vitro as possible antitrypanosomal compounds. Some derivatives showed a slight activity. As they are structurally related to glutathione, their inhibitory properties towards glutathionylspermidine synthetase, trypanothione synthetase and trypanothione reductase were determined. No inhibitory activity was found.

  DOI：

  10.1016/0223-5234(93)90125-x

文献信息

• Synthesis and antitrypanosomal evaluation of some thiazole-containing amino acids and peptides
  作者：I Van Bogaert、A Haemers、W Bollaert、N Van Meirvenne、R Brun、K Smith、AH Fairlamb

  DOI：10.1016/0223-5234(93)90125-x

  日期：1993.1

  Several amino acids and peptides containing thiazole and thiazolidine residues were prepared. They were tested in vivo and in vitro as possible antitrypanosomal compounds. Some derivatives showed a slight activity. As they are structurally related to glutathione, their inhibitory properties towards glutathionylspermidine synthetase, trypanothione synthetase and trypanothione reductase were determined. No inhibitory activity was found.
• Sulfur ylides 13. Synthesis and intramolecular cyclization of keto-stabilized sulfur ylides
  作者：F. Z. Galin、I. M. Sakhautdinov、S. N. Lakeev、V. A. Egorov、A. A. Fatykhov、I. O. Maidanova

  DOI：10.1007/s11172-006-0202-6

  日期：2005.12

  were obtained from N-phthalylglutamic acid and their intramolecular cyclization was studied. The intramolecular cyclization of the ylide obtained at the α-carboxy group gave a product of the pyrrolizidinedione structure; bisylide yielded a cycloheptene derivative as the result of intramolecular recombination of intermediate dicarbene. The ylide obtained at the γ-carboxy group underwent no cyclization

  从 N-邻苯二甲酰谷氨酸中获得了酮稳定的硫单和双硫醚，并研究了它们的分子内环化。在α-羧基上得到的叶立德分子内环化得到吡咯里西啶二酮结构的产物；作为中间体双卡宾分子内重组的结果，双酰化物产生了环庚烯衍生物。在 γ-羧基上得到的叶立德没有进行环化，得到甲硫酮和氧代苯甲酸酯。