Methyl 4-bromo-2-phthalimidobutyrate | 122690-13-5

• 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 4-bromo-2-phthalimidobutyrate
• 英文别名: Methyl 4-bromo-2-(1,3-dioxoisoindol-2-yl)butanoate
• CAS: 122690-13-5
• 化学式: C₁₃H₁₂BrNO₄
• 分子量: 326.147
• InChiKey: MKVUTORSRWEXEU-UHFFFAOYSA-N

物化性质

• 沸点：
  428.1±40.0 °C(Predicted)
• 密度：
  1.595±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl 4-bromo-2-phthalimidobutyrate 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以87%的产率得到methyl 1-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)cyclopropanecarboxylate
  参考文献：
  名称：

  Facile synthesis of D,L-phosphinothricin from methyl 4-bromo-2-phthalimidobutyrate

  摘要：

  DOI：

  10.1016/s0040-4039(00)85366-6
• 作为产物：
  描述：

  4-bromo-2-phthalimidobutyric acid 、 重氮甲烷 生成 Methyl 4-bromo-2-phthalimidobutyrate
  参考文献：
  名称：

  LOGUSCH, EUGENE W.

  摘要：

  DOI：

文献信息

• Synthesis of α,ω-polyfluorinated α-amino acid derivatives and δ,δ-difluoronorvaline
  作者：Dirk Ulbrich、Constantin G. Daniliuc、Günter Haufe

  DOI：10.1039/c6ob00131a

  日期：——

  Intending to synthesize ω,ω-difluoroalkyl amino acid derivatives by oxidative desulfurization–fluorination reactions of suitable arylthio-2-phthalimido butanoates and pentanoates, in addition to small amounts of the target products, mainly α,ω-polyfluorinated amino acid derivatives were formed by additional sulfur-assisted α-fluorination. This novel structural motif was verified spectroscopically as

  打算通过合适的芳硫基-2-邻苯二甲酰亚胺基丁酸酯和戊酸酯的氧化脱硫-氟化反应合成ω，ω-二氟烷基氨基酸衍生物，除少量目标产物外，主要由α，ω-多氟氨基酸衍生物形成额外的硫辅助α-氟化。该新颖的结构基序在光谱学上以及通过X射线分析得到了验证。提出了合理的形成机理。使用不同的方法，通过相应醛的脱氧氟化合成了δ，δ-二氟正缬氨酸盐酸盐，其对映体过量至少36％。
• Transesterification of trialkyl phosphates from alkyl bromides
  作者：Christian Lherbet、Roselyne Castonguay、Jeffrey W. Keillor

  DOI：10.1016/j.tetlet.2005.03.065

  日期：2005.5

  The treatment of trialkyl phosphate with different alkyl bromides provides facile access to mixed phosphate esters. The presence of substoichiometric amounts of lithium bromide was found to be critical to this transesterification process, supporting a mechanism involving initial generation of phosphate anion, followed by its nucleophilic attack on alkyl bromide.

  用不同的烷基溴处理磷酸三烷基酯可轻松获得混合磷酸酯。发现亚化学计量量的溴化锂的存在对该酯交换过程至关重要，这支持了一种机制，该机制涉及最初生成磷酸根阴离子，然后其亲核性攻击烷基溴。
• 4-phosphorus-2-phthalimidobutyrate intermediates
  申请人：Monsanto Company

  公开号：US04764620A1

  公开（公告）日：1988-08-16

  Phosphinylbutanoic acids, such as phosphinothricin, can be prepared by reacting racemic 4-halo-2-phthalimidobutyrates with a tricoordinate phosphorus compound represented by the formula: R.sup.1 --P--(R.sup.2).sub.2 wherein R.sup.1 is methyl or ethyl, and R.sup.2 is selected from the group consisting of alkoxy having from one to six carbon atoms, aryloxy, and trialkylsilyloxy groups having from one to twelve carbon atoms, to form an intermediate compound; and hydrolyzing the intermediate compound to form the phosphinylbutanoic acids.

  磷酰丁酸，如磷氨基丙酸，可以通过将外消旋的4-卤代-2-邻苯二甲酰丁酸酯与一种三配位磷化合物反应而制备，该磷化合物的结构式表示为：R.sup.1 --P--(R.sup.2).sub.2，其中R.sup.1为甲基或乙基，R.sup.2选自具有1至6个碳原子的烷氧基、芳基氧基和具有1至12个碳原子的三烷基硅氧基基团，以形成中间化合物；然后水解中间化合物以形成磷酰丁酸。
• Facile synthesis of 4-N-phosphonomethyl-2,4-diamino-butyrates as inhibitors of glutamine synthetase
  作者：Eugene W. Logusch、Daniel R. Dukesherer、Kathleen M. Getman、John E. Franz

  DOI：10.1016/0040-4039(91)85065-d

  日期：1991.6

  An effective synthesis of N-substituted 2,4-diaminobutyric acids is described involving reaction of amines with methyl 4-bromo-2-phthalimidobutyrate, followed by hydrolysis. This approach was applied to the synthesis of 4-N-phosphonomethyl-2,4-diaminobutyric acids as inhibitors of glutamine synthetase.

  描述了一种N-取代的2，4-二氨基丁酸的有效合成方法，该方法包括使胺与4-溴-2-邻苯二甲酰亚胺基丁酸甲酯反应，然后进行水解。该方法被应用于作为谷氨酰胺合成酶抑制剂的4 - N-膦酰基甲基-2,4-二氨基丁酸的合成。
• 2-Amino-4-Phosphonyl-butanoate derivates and preparation of 2-amino-4-phosphinyl butanoic acids
  申请人：Monsanto Company

  公开号：EP0265412A2

  公开（公告）日：1988-04-27

  Phosphinylbutanoic acids, such as phosphino­thricin, can be prepared by reacting racemic 4-halo-2-­phthalimidobutyrates with a tricoordinate phosphorus compound represented by the formula:     R¹ - P - (R²)₂ wherein R¹ is methyl or ethyl, and R² is selected from the group consisting of alkoxy having from one to six carbon atoms, aryloxy, and trialkylsilyloxy groups having from one to twelve carbon atoms, to form an intermediate compound; and hydrolyzing the intermediate compound to form the phosphinylbutanoic acids.

  外消旋 4-卤代-2-邻苯二甲酰亚胺丁酸与三配位磷化合物反应，可制备膦酰基丁酸，如膦酰三嗪： R¹ - P - (R²)₂ 其中 R¹ 为甲基或乙基，R² 选自具有 1 至 6 个碳原子的烷氧基、芳氧基和具有 1 至 12 个碳原子的三烷基硅氧基所组成的组，形成中间化合物；水解中间化合物形成膦酰丁酸。