Sphenyl N-benzyloxycarbonylaminoethanothioate | 2899-57-2

• 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: Sphenyl N-benzyloxycarbonylaminoethanothioate
• 英文别名: N-benzyloxycarbonyl-thioglycine S-phenyl ester；N-Benzyloxycarbonyl-thioglycin-S-phenylester；N-Benzyloxycarbonyl-glycin-phenylthioester；Benzyloxycarbonyl-glycin-thiophenylester；Benzyloxycarbonyl-glycin-thiophenylether；N-Carbobenzoxyglycin-thiophenylester；S-phenyl 2-(phenylmethoxycarbonylamino)ethanethioate
• CAS: 2899-57-2
• 化学式: C₁₆H₁₅NO₃S
• 分子量: 301.366
• InChiKey: GCMWCYAOLDVUSV-UHFFFAOYSA-N

物化性质

• 熔点：
  72 °C
• 沸点：
  480.0±38.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Sphenyl N-benzyloxycarbonylaminoethanothioate 在 三氟乙酸 作用下， 生成 H-Gly-SPh
  参考文献：
  名称：

  Notizen: Entcarbobenzoxylierung von Aminosäuren und Derivaten mit wasserfreier Trifluoressigsäure

  摘要：

  DOI：

  10.1515/znb-1959-0723
• 作为产物：
  描述：

  苯基氯硫代甲酸酯 、 N-苄氧羰基甘氨酸 生成 Sphenyl N-benzyloxycarbonylaminoethanothioate
  参考文献：
  名称：

  Itoh,M., Chemical and pharmaceutical bulletin, 1970, vol. 18, # 4, p. 784 - 788

  摘要：

  DOI：

文献信息

• The Trifluoroacetate Method of Peptide Synthesis. I. The Synthesis and Use of Trifluoroacetate Reagents
  作者：Shumpei Sakakibara、Noriyoshi Inukai

  DOI：10.1246/bcsj.38.1979

  日期：1965.11

  thiophenol and N-hydroxyimide derivatives, which are known as hydroxylic partners of various active carboxylic acid ester, have been synthesized, and it has been found that they are good reagents for the preparation of the respective active esters of acylamino acids by the ester-exchange reaction in pyridine. The new method is especially effective in the preparation of p-nitrophenyl, 2,4,5-trichlorophenyl

  合成了各种苯酚、苯硫酚和N-羟基酰亚胺衍生物的三氟乙酸酯，它们被称为各种活性羧酸酯的羟基伴侣，并发现它们是制备相应酰氨基活性酯的良好试剂。在吡啶中通过酯交换反应生成酸。新方法在制备对硝基苯基、2,4,5-三氯苯基和酰基氨基酸的 N-羟基琥珀酰亚胺酯方面特别有效，它们是众所周知的有用的肽合成中间体。已经研究了使用这些试剂直接合成肽而不分离中间体，并且发现新的程序是肽的明智延伸。
• Synthesis of activated esters of N-protected amino-acids
  作者：Y. Wolman、D. Ladkany、Max Frankel

  DOI：10.1039/j39670000689

  日期：——

  A simplified method for the synthesis of activated esters of N-protected amino-acids is described. The synthesis proceeds through the aminolysis of various active esters of t-butyl or benzyl carbonate, and the leaving group displaced in this process becomes reincorporated by the additon of dicyclohexylcarbodi-imide to the reaction mixture, to give the desired compound.

  描述了一种用于合成N-保护的氨基酸的活化酯的简化方法。合成通过碳酸叔丁酯或碳酸苄酯的各种活性酯的氨解进行，并且在该过程中置换的离去基团通过将二环己基碳二亚胺添加到反应混合物中而重新结合，从而得到所需化合物。
• A Facile General Synthesis of Thiocarboxylate<i>S</i>-Esters of Glyphosate and Its Derivatives
  作者：Michael K. Mao、John E. Franz

  DOI：10.1055/s-1991-26606

  日期：——

  Various glyphosate thiocarboxylate S-ester derivatives, e.g. S-alkyl 2-(phosphonomethylamino)ethanethioates and S-alkyl 2-[(phenoxyphosphorylmethyl)amino]ethanethioates, are readily synthesized from N-benzyloxycarbonylglycine using N-methylene-tert-butylamine as the methylene transfer reagent followed by nucleophilic phosphorylation with tris(trimethylsilyl) phosphite.

  各种草甘膦硫羧酸酯S-酯衍生物，例如S-烷基2-(膦甲基氨基)乙硫酸盐和S-烷基2-[(苯氧膦酰基甲基)氨基]乙硫酸盐，可以通过使用N-亚苄氧羧基甘氨酸和N-亚甲基-叔丁胺作为亚甲基转移试剂，然后通过与三(三甲基硅基)磷酸酯进行亲核磷酸化反应，容易合成。
• The mass spectra of amino-acid and peptide derivatives. Part I. Benzyloxycarbonyl derivatives
  作者：R. T. Aplin、J. H. Jones、B. Liberek

  DOI：10.1039/j39680001011

  日期：——

  a benzyloxy-radical in addition to showing the well recognised cleavages of the peptide bonds and side-chains. Cleavage of the peptide bond gives important fragments of type PhCH2·O·CO·[graphic omitted]H:CHR which then lose carbon dioxide with concomitant migration of the benzyl group. Some benzyloxycarbonyl amino-acid and dipeptide phenylthio-esters have also been examined: the peak of highest m/e

  N-苯甲氧基羰基二肽烷基酯产生大量的分子离子，除了显示出公认的肽键和侧链裂解以外，其还失去了苄氧基自由基。肽键的裂解产生了PhCH 2 ·O·CO·[H]：CHR类型的重要片段，该片段随后损失了二氧化碳，并伴随着苄基的迁移。还检测了一些苄氧羰基氨基酸和二肽苯硫基酯：m / e最高的峰这些化合物的光谱中的“α”对应于苯硫基自由基的损失而形成的acy离子。有人建议苯硫代酯可以在“触发”逐步消除羧基末端氨基酸残基的质谱分析中找到应用。
• Synchrotron radiography and x-ray topography studies of hexagonal habitus SiC bulk crystals
  作者：T. S. Argunova、M. Yu. Gutkin、Jung Ho Je、H. S. Kang、Y. Hwu、W-L. Tsai、G. Margaritondo

  DOI：10.1557/jmr.2002.0391

  日期：2002.10

  Phase-sensitive synchrotron radiation (SR) radiography was combined with x-ray diffraction topography to study structural defects of SiC crystals. The particular bulk SiC crystals examined had a low micropipe density and a hexagonal habitus composed of prismatic, pyramidal, and basal faces well developed. X-ray diffraction topography images of the sliced (0001) wafers, which were formed due to the complex lattice distortions associated with defective boundaries, demonstrated the existence of two-dimensional defective boundaries in the radial direction, normal to the (0001) planes. In particular, those parallel to the 〈1120〉 directions extended rather far from the seed. On the other hand, by phase-sensitive SR radiography the effect of micropipe collection was detected. Micropipes grouped mostly in the vicinities of the defective boundaries but rarely appeared between groups. Some general remarks about possible reasons for the development of such peculiar defect structures were made.

  相敏同步辐射（SR）射线照相术与 X 射线衍射拓扑图相结合，研究了碳化硅晶体的结构缺陷。所研究的特定块状碳化硅晶体具有较低的微管密度和由棱柱面、金字塔面和基底面组成的发育良好的六边形习性。切片 (0001) 硅片的 X 射线衍射拓扑图像是由于与缺陷边界相关的复杂晶格畸变而形成的，它表明在 (0001) 平面的法线径向存在二维缺陷边界。特别是，那些平行于〈1120〉方向的缺陷边界离种子相当远。另一方面，通过相敏 SR 射线照相术，可以检测到微管聚集的影响。微管主要聚集在缺陷边界附近，但很少出现在群组之间。对形成这种特殊缺陷结构的可能原因进行了一些一般性评论。