9H-芴-9-基甲基 [(2S)-3-(苄氧基)-1-氯-1-氧代-2-丙基]氨基甲酸酯 | 157506-72-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: 9H-芴-9-基甲基 [(2S)-3-(苄氧基)-1-氯-1-氧代-2-丙基]氨基甲酸酯
• 中文别名: 9H-芴-9-基甲基[(2S)-3-(苄氧基)-1-氯-1-氧代-2-丙基]氨基甲酸酯；肽酰胺酶
• 英文名称: Fmoc-L-(Bn)Ser-Cl
• 英文别名: Fmoc-(OBn)Ser-Cl；Fmoc-L-Ser(OBn)-Cl；Fmoc-O-benzyl-L-seryl chloride；9H-fluoren-9-ylmethyl N-[(2S)-1-chloro-1-oxo-3-phenylmethoxypropan-2-yl]carbamate
• CAS: 157506-72-4
• 化学式: C₂₅H₂₂ClNO₄
• 分子量: 435.907
• InChiKey: CNSWGDFBUSGOOY-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9H-芴-9-基甲基 [(2S)-3-(苄氧基)-1-氯-1-氧代-2-丙基]氨基甲酸酯 在 盐酸羟胺 、 magnesium oxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以85%的产率得到((S)-2-Benzyloxy-1-hydroxycarbamoyl-ethyl)-carbamic acid 9H-fluoren-9-ylmethyl ester
  参考文献：
  名称：

  Direct synthesis of Fmoc protected amino acid hydroxamates from acid chlorides mediated by magnesium oxide

  摘要：

  The synthesis of Fmoc protected amino acid hydroxamates using Fmoc-amino acid chlorides and magnesium oxide is described. The method is simple and efficient, results in complete conversion, and gives good yields and satisfactory purity. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00830-x
• 作为产物：
  描述：

  Fmoc-O-苄基-L-丝氨酸 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以90.8%的产率得到9H-芴-9-基甲基 [(2S)-3-(苄氧基)-1-氯-1-氧代-2-丙基]氨基甲酸酯
  参考文献：
  名称：

  (Fluoren-9-ylmethoxy)carbonyl (Fmoc) amino acid chlorides. Synthesis, characterization, and application to the rapid synthesis of short peptide segments

  摘要：

  DOI：

  10.1021/jo00369a042

文献信息

• HOBt·DCHA-Mediated Synthesis of Sterically Hindered Peptides employing Fmoc-Amino Acid Chlorides in Both Solution-Phase and Solid Phase Methods
  作者：Vommina V. Sureshbabu、Naremaddepalli S. Sudarshan、G. Chenna Krishna

  DOI：10.1080/00397910802219536

  日期：2008.7.24

  Abstract The synthesis of peptides employing Fmoc-amino acid chlorides in presence of HOBt·DCHA salt in solution as well as by the solid-phase methods is described. The coupling was found to be complete in 30 min and free from racemization. The synthesis of β-casomorphin by solid-phase protocol employing Fmoc-amino acid chloride/HOBt·DCHA in DMF–CH2Cl2 has also been outlined. The final peptide was

  摘要 描述了在溶液中存在 HOBt·DCHA 盐的情况下使用 Fmoc-氨基酸氯化物以及固相方法合成肽。发现偶联在 30 分钟内完成并且没有外消旋。还概述了使用 Fmoc-氨基酸氯化物/HOBt·DCHA 在 DMF-CH2Cl2 中通过固相方案合成 β-酪啡肽。最终的肽以 80% 的产率获得并被充分表征。
• Chemical genetics approach to identify new small molecule modulators of cell growth by phenotypic screening of Saccharomyces cerevisiae strains with a library of morpholine-derived compounds
  作者：Andrea Trabocchi、Irene Stefanini、Manfredi Morvillo、Leonardo Ciofi、Duccio Cavalieri、Antonio Guarna

  DOI：10.1039/c0ob00357c

  日期：——

  with a pool of morpholine-derived compounds in order to identify candidate small molecules able to produce phenotypic effects on yeast cells. The analysis of the effects of structurally diverse molecules towards cell growth rate in both exponential and stationary phases provides a tool to select candidate compounds for subsequent assays to identify new chemical entities as chemical probes for drug discovery

  化学遗传学方法已用于筛选具有吗啉衍生化合物库的酵母缺失菌株，以鉴定能够在酵母细胞上产生表型效应的候选小分子。对不同结构的分子对指数期和固定期细胞生长速率的影响的分析提供了一种工具，可以选择候选化合物进行后续测定，以鉴定新的化学实体作为药物发现的化学探针。
• Synthesis of N-Urethane Protected α-Aminoalkyl-α′-cyanomethyl Ketones; Application to the Synthesis of 3-Substituted 5-Amino-1H-pyrazole Tethered Peptidomimetics
  作者：Vommina Sureshbabu、M. Sharnabai、G. Nagendra

  DOI：10.1055/s-0032-1316586

  日期：2012.8

  The preparation of N-protected amino/peptide alpha-cyanomethyl ketones through cyanation of the corresponding alpha-bromomethyl ketones is described. The utility of the resulting acyanomethyl ketones in the synthesis of 3-substituted-5-amino-1H-pyrazoles has also been demonstrated. In both steps a wide range of N-protected amino/peptide acids has been employed and the products are obtained in good yield. The enantiomeric purity of both the alpha-cyanomethyl ketones and pyrazoles were confirmed by chiral HPLC analysis of the corresponding Z-protected D-and L-Ala-OH as model substrates. The synthesis of peptide pyrazolecarbox-amides is also delineated.
• Skeletal diversity by sequential one-pot and stepwise routes using morpholine ester scaffolds
  作者：Leonardo Ciofi、Manfredi Morvillo、Filippo Sladojevich、Antonio Guarna、Andrea Trabocchi

  DOI：10.1016/j.tetlet.2010.09.103

  日期：2010.12

  A skeletal diversity approach starting from morpholine acetals has been achieved by tuning a three-step process from stepwise to sequential one-pot to provide diverse scaffolds containing either a 2-oxopiperazine or a diketopiperazine skeleton. (C) 2010 Elsevier Ltd. All rights reserved.
• Dipeptide Surrogates Containing Asparagine-Derived Tetrahydropyrimidinones:  Preparation, Structure, and Use in Solid Phase Synthesis
  作者：Joseph P. Konopelski、Lubov K. Filonova、Marilyn M. Olmstead

  DOI：10.1021/ja9639271

  日期：1997.5.1