tert-Butyl N-glycinate | 58091-07-9

• 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: tert-Butyl N-glycinate
• 英文别名: Tert-butyl 2-[bis(methylsulfanyl)methylideneamino]acetate
• CAS: 58091-07-9
• 化学式: C₉H₁₇NO₂S₂
• 分子量: 235.371
• InChiKey: ICZCMQVDZWTKNL-UHFFFAOYSA-N

物化性质

• 沸点：
  298.3±19.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  89.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-Butyl N-glycinate 在 苄基三乙基氯化铵 盐酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 26.0h， 生成 trans-5-(tert-Butoxycarbonyl)-2-ethyl-4-methyl-Δ¹-pyrroline
  参考文献：
  名称：

  Diastereoselective Synthesis of Substituted Glutamic Acid Derivatives via Michael Additions of N-[Bis(methylthio)methylene]glycinates under Solid-Liquid Phase Transfer Catalysis

  摘要：

  Michael additions of the enolates of ethyl and tert-butyl N-[bis(methylthio)methylene]glycinates with alpha,beta-unsaturated esters and ketones under solid-liquid phase transfer catalysis allowed for the highly diastereoselective synthesis of substituted glutamic acid derivatives through a transition state chelation-controlled by the catalyst with a like approach of reactants. Selective removal of the iminodithiocarbonate protecting group with concomitant cyclization gave rise to 3-substituted pyroglutamates and 1,3,4-trisubstitued Delta(1)-pyrrolines with retention of configuration.

  DOI：

  10.1021/jo00126a020
• 作为产物：
  描述：

  叠氮基乙酸叔丁酯 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 0.0h， 生成 tert-Butyl N-glycinate
  参考文献：
  名称：

  通过亚氨基二硫代碳酸酯与叠氮烯酮的环加成反应合成β-内酰胺。

  摘要：

  DOI：

  10.1021/jo00869a006

文献信息

• Asymmetric Oxidative Dimerization of the Enolates of <i>N</i>-[Bis(methylthio)methylene]- and <i>N</i>-(Diphenylmethylene)glycine Esters
  作者：Carlos Alvarez-Ibarra、Aurelio G. Csákÿ、Belén Colmenero、M. Luz Quiroga

  DOI：10.1021/jo962116c

  日期：1997.4.1

  The oxidative dimerization of glycinates 1 with iodine takes place under kinetic control. The stereochemistry of the resulting 3-aminoaspartate 3 depends on the method used (base/solvent) to generate the corresponding enolate 2. Under suitable conditions, high yields and diastereomeric excesses in favor of the threo derivatives 3-I, which have C(2) symmetry, were obtained. In the presence of 8-phenylmenthol

  甘氨酸盐1与碘的氧化二聚反应是在动力学控制下进行的。生成的3-氨基天冬氨酸3的立体化学取决于所用的方法（碱/溶剂），以生成相应的烯醇盐2。在合适的条件下，高收率和非对映体过量有利于苏式衍生物3-I，其具有C（2 ）对称。在存在8-苯基薄荷醇作为手性助剂（2S，3S）-3-氨基天冬氨酸5-I的情况下。
• α-Amination and the 5-exo-trig cyclization reaction of sulfur-containing Schiff bases with N -phenyltriazolinedione and their anti-lipid peroxidation activity
  作者：Emel Pelit、Kosmas Oikonomou、Melek Gul、Dimitra Georgiou、Slawomir Szafert、Sotirios Katsamakas、Dimitra Hadjipavlou-Litina、Yiannis Elemes

  DOI：10.1016/j.crci.2016.05.024

  日期：2017.4

  Résumé Triazolinedione quenches efficiently the 1,2-dipoles from Schiff bases of glycine esters which are formed via a [1,2-H]-prototropic shift of their α-hydrogens, and affords the respective α-aminated products in good yields. Competition experiments show a stabilization of the 1,2-dipole from the sulfide substituent. 5-exo-trig cyclization of N-PhTAD with Schiff bases of other amino acids gave triazolines. The antioxidative and lipoxygenase inhibitory activities of the novel synthesized compounds were studied. Supplementary Materials: Supplementary material for this article is supplied as a separate file: mmc1.docx

  三唑啉二酮可有效猝灭甘氨酸酯席夫碱的 1,2-偶极子，甘氨酸酯是通过其 α-氢的 [1,2-H]-质子转移而形成的，并以良好的产率提供相应的 α-胺化产物。竞争实验表明，硫化物取代基的 1,2-偶极子具有稳定性。 N-PhTAD 与其他氨基酸的席夫碱进行 5-exo-trig 环化，得到三唑啉。研究了新合成化合物的抗氧化和脂氧合酶抑制活性。 补充材料：本文的补充材料作为单独的文件提供：mmc1.docx
• Reaction of N-[bis(methylthio)methylene]glycinates with electron deficient alkynes. Synthesis of (Z)-α,β-didehydroglutamic acid derivatives
  作者：Carlos Alvarez-Ibarra、Aurelio G Csákÿ、Elena Martín Ortega、M Jesús de la Morena、M Luz Quiroga

  DOI：10.1016/s0040-4039(97)00913-1

  日期：1997.6

  The addition of either the alkaline enolates of the glycinates 1 or their naked enolates to electron defficient alkynes allows for the synthesis of substituted (Z)-alpha,beta-didehydroglutamic acid derivatives 7 via a Michael addition/1,3-prototropic rearrangement sequence. (C) 1997 Elsevier Science Ltd.
• Synthesis of sulfur containing dihydro-pyrrolo derivatives and their biological evaluation as antioxidants
  作者：Dimitra Georgiou、Vasilios Toutountzoglou、Kenneth W. Muir、Dimitra Hadjipavlou-Litina、Yiannis Elemes

  DOI：10.1016/j.bmc.2012.07.014

  日期：2012.9

  The 1,3-dipolar cycloaddition to N-phenylmaleimide of azomethine ylides, generated in situ from sulfanyl-substituted imines of glycine esters, yields 5H-dihydro-pyrrolo products with syn diastereoselectivity. The syn (major) and anti (minor) products were isolated chromatographically and fully characterized by spectroscopic methods and in two cases also by X-ray analysis. The diastereomeric cycloadducts were tested for their antioxidant activity with good results. (C) 2012 Elsevier Ltd. All rights reserved.
• Diastereoselective Synthesis of Substituted Glutamic Acid Derivatives via Michael Additions of N-[Bis(methylthio)methylene]glycinates under Solid-Liquid Phase Transfer Catalysis
  作者：Carlos Alvarez-Ibarra、Aurelio G. Csakye、Mercedes Maroto、M. Luz Quiroga

  DOI：10.1021/jo00126a020

  日期：1995.10

  Michael additions of the enolates of ethyl and tert-butyl N-[bis(methylthio)methylene]glycinates with alpha,beta-unsaturated esters and ketones under solid-liquid phase transfer catalysis allowed for the highly diastereoselective synthesis of substituted glutamic acid derivatives through a transition state chelation-controlled by the catalyst with a like approach of reactants. Selective removal of the iminodithiocarbonate protecting group with concomitant cyclization gave rise to 3-substituted pyroglutamates and 1,3,4-trisubstitued Delta(1)-pyrrolines with retention of configuration.