(R)-tert-butyl 1-(benzylamino)-1-oxo-3-phenylpropan-2-ylcarbamate | 114530-49-3

• 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: (R)-tert-butyl 1-(benzylamino)-1-oxo-3-phenylpropan-2-ylcarbamate
• 英文别名: (S)-N-Boc-phenylalanine benzylamide；(1-Benzylcarbamoyl-2-phenyl-ethyl)-carbamic acid tert-butyl ester；tert-butyl N-[1-(benzylamino)-1-oxo-3-phenylpropan-2-yl]carbamate
• CAS: 114530-49-3
• 化学式: C₂₁H₂₆N₂O₃
• 分子量: 354.449
• InChiKey: BHFUBRBEEFGRHT-UHFFFAOYSA-N

物化性质

• 沸点：
  578.2±50.0 °C(Predicted)
• 密度：
  1.117±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-tert-butyl 1-(benzylamino)-1-oxo-3-phenylpropan-2-ylcarbamate 在 甲酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 120.0h， 以215 mg的产率得到2-氨基-N-苄基-3-苯基丙酰胺
  参考文献：
  名称：

  基于离子树脂捕获的同时脱保护和纯化：在酰胺形成以及格氏和光信反应中的应用

  摘要：

  通过同时裂解保护基团，将含有 Boc-或 Tr-保护胺的产物直接从反应混合物中捕获。通过用氨释放产物，以高产率和纯度获得相应的游离胺。基于离子树脂捕获的广泛适用的同时脱保护和纯化方法被应用于格氏反应和光信反应以及酰胺形成，并显示出多平行合成的高潜力。

  DOI：

  10.1055/s-2007-983758
• 作为产物：
  描述：

  N-甲基-N-叔丁氧羰基-D-苯丙氨酸 在 N-甲基吗啉 作用下， 以 四氢呋喃 为溶剂， 反应 3.75h， 生成 (R)-tert-butyl 1-(benzylamino)-1-oxo-3-phenylpropan-2-ylcarbamate
  参考文献：
  名称：

  Design and Synthesis of Mimics of the T7-loop of FtsZ

  摘要：

  Mimics of the 17-loop of the bacterial cell division protein FtsZ have been designed and synthesized. The design is based on the X-ray cocrystal structure of P. aeruginosa FtsZ:SulA. Fast Rigid Exhaustive Docking (FRED) was employed to select compounds that can mimic the key interacting residues. Bicyclic oxazolidinones 1a-d were selected for further study and synthesized from a key bicyclic aziridine intermediate, which is synthesized from a readily available unsaturated aldehyde and amides derived from a-amino acids.

  DOI：

  10.1021/ol4010068

文献信息

• Simultaneous Deprotection and Purification Based on Ionic Resin Capture: Application to Amide Formations and Grignard and Mitsunobu Reactions
  作者：Peter Meier、Sascha Müller

  DOI：10.1055/s-2007-983758

  日期：——

  Tr-protected amines were caught directly out of reaction mixtures by simultaneous cleavage of the protecting group. By releasing the products with ammonia the corresponding free amines were obtained in high yields and purities. The broadly applicable method of simultaneous deprotection and purification based on ionic resin capture was applied for Grignard and Mitsunobu reactions as well as amide formations

  通过同时裂解保护基团，将含有 Boc-或 Tr-保护胺的产物直接从反应混合物中捕获。通过用氨释放产物，以高产率和纯度获得相应的游离胺。基于离子树脂捕获的广泛适用的同时脱保护和纯化方法被应用于格氏反应和光信反应以及酰胺形成，并显示出多平行合成的高潜力。
• A novel solid-phase chlorinating reagent for the synthesis of acyl chlorides
  作者：Guanglin Luo、Li Xu、Graham S. Poindexter

  DOI：10.1016/s0040-4039(02)02190-1

  日期：2002.12

  Cyanuric chloride was loaded onto a modified Wang resin, which was successfully used to convert carboxylic acids to their corresponding acyl chlorides. The formation of acyl chlorides were confirmed by condensation with various amines or alcohols to form the corresponding amides or esters.

  将氰尿酰氯装载到改性的Wang树脂上，该树脂成功地用于将羧酸转化为其相应的酰氯。通过与各种胺或醇缩合形成相应的酰胺或酯，可以确认酰氯的形成。
• Peptidomimetic bond formation by DNA-templated acyl transfer
  作者：Mireya L. McKee、Amanda C. Evans、Simon R. Gerrard、Rachel K. O'Reilly、Andrew J. Turberfield、Eugen Stulz

  DOI：10.1039/c0ob00753f

  日期：——

  The efficiencies of DNA-templated acyl transfer reactions between a thioester modified oligonucleotide and a series of amine and thiol based nucleophiles are directly compared. The reactivity of the nucleophile, reaction conditions (solvent, buffer, pH) and linker length all play important roles in determining the efficiency of the transfer reaction. Careful optimisation of the system enables the use of DNA-templated synthesis to form stable peptide-like bonds under mild aqueous conditions close to neutral pH.

  直接比较硫酯修饰寡核苷酸与一系列胺和硫醇类亲核试剂之间DNA模板酰基转移反应的效率。亲核试剂的反应性、反应条件（溶剂、缓冲液、pH值）和连接子长度在决定转移反应的效率方面都起着重要作用。通过对系统进行仔细优化，可以在接近中性pH值的温和水溶液条件下利用DNA模板合成形成稳定的肽键。
• Protonated<i>N</i>-benzyl- and<i>N</i>-(1-phenylethyl)tyrosine amides dissociate via ion/neutral complexes
  作者：Justin Paulose、Revi P. Achuthan、Maria P. L. Linsha、George Mathai、B. Prasanth、M. V. N. Kumar Talluri、Ragampeta Srinivas

  DOI：10.1002/rcm.7256

  日期：2015.9.15

  cation partner. The [M+H]+ ion of N-(1-phenylethyl)tyrosine amide rearranges to an INC of the 1-phenylethyl cation. Subsequent elimination of styrene occurs by transfer of a proton from the 1-phenylethyl cation to the neutral partner. CONCLUSIONS The [M+H]+ ions of both N-benzyl (1) and N-(1-phenylethyl) (2) tyrosine amide rearrange into INCs. The dissociation of [M+H]+ ion of 1 yields the benzyl cation

  理由已提出具有与N原子相连的苄基的分子的[M + H] +离子的碰撞诱导解离（CID）涉及苄基通过离子/中性络合物（INC）的中间迁移。我们报告了电喷雾电离（ESI）串联质谱（MS / MS）和密度泛函理论（DFT）计算的质子化N-苄基和N-（1-苯乙基）酪氨酸酰胺解离机理的研究。方法酰胺是由相应的氨基酸和胺合成的。使用Agilent QTOF 6540质谱仪记录ESI-MS / MS光谱。DFT计算是通过使用Gaussian 09软件进行的。在B3LYP / 6-31G（d，p）的理论水平上优化了[M + H] +离子，中间体，产物和过渡态（TS）的结构。结果由于重排，N-苄基酪氨酸酰胺的[M + H] +离子的CID产生两个产物离子：（i）由于苄基向羟基苯基的迁移，[M + H-74] +离子（m / z 197）环和（ii）[M + H-45] +离子（m / z 226），原因是苄
• Design and Synthesis of Mimics of the T7-loop of FtsZ
  作者：Nohemy A. Sorto、Phillip P. Painter、James C. Fettinger、Dean J. Tantillo、Jared T. Shaw

  DOI：10.1021/ol4010068

  日期：2013.6.7

  Mimics of the 17-loop of the bacterial cell division protein FtsZ have been designed and synthesized. The design is based on the X-ray cocrystal structure of P. aeruginosa FtsZ:SulA. Fast Rigid Exhaustive Docking (FRED) was employed to select compounds that can mimic the key interacting residues. Bicyclic oxazolidinones 1a-d were selected for further study and synthesized from a key bicyclic aziridine intermediate, which is synthesized from a readily available unsaturated aldehyde and amides derived from a-amino acids.