(±)-cis-3-(9-fluorenylmethyloxycarbonyl)aminobicyclo[2.2.1]heptane-2-carboxylic acid | 352707-75-6

• 物质功能分类: 生物化工 - 生化试剂 - 氨基酸
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (±)-cis-3-(9-fluorenylmethyloxycarbonyl)aminobicyclo[2.2.1]heptane-2-carboxylic acid
• 英文别名: (±)-cis-3-(FMOC-amino)bicyclo[2.2.1]heptane-2-carboxylicacid；N-Fmoc-(+/-)cis (exo)-3-amino-bicyclo[2.2.1]heptane-2-carboxylic acid；(1S,2R,3S,4R)-3-(9H-fluoren-9-ylmethoxycarbonylamino)bicyclo[2.2.1]heptane-2-carboxylic acid
• CAS: 352707-75-6
• 化学式: C₂₃H₂₃NO₄
• 分子量: 377.44
• InChiKey: RAQPAPMBITVVOX-HLNGLMCHSA-N

物化性质

• 沸点：
  605.2±34.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  29225090,2924299090

反应信息

• 作为反应物：
  描述：

  Fmoc-L-亮氨酸 、 (±)-cis-3-(9-fluorenylmethyloxycarbonyl)aminobicyclo[2.2.1]heptane-2-carboxylic acid 在 N,N'-二异丙基碳二亚胺 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 24.5h， 生成 (1R,2S,8R,9S)-5S-isobutyl-3,6-diazatricyclo[7.2.1.0^2,8]dodecane-4,7-dione
  参考文献：
  名称：

  Solid-phase synthesis of 6,7-cycloalkane-fused 1,4-diazepane-2,5-diones via a cyclization/release strategy

  摘要：

  A solid-phase synthesis procedure for the parallel preparation of 6,7-cycloalkane-fused 1,4-diazepane-2,5-diones is described. The methodology applies alpha- and alicyclic beta-amino acid building blocks to construct the seven-membered heterocyclic core, while alcohols are used for further skeletal decoration. The use of a cyclization/release strategy permits the isolation of the target cyclic alpha,beta-dipeptides in good crude purities and generally moderate to good yields. A 26-membered model library is reported and NMR spectroscopical data are used to describe the overall conformational behaviour of the obtained homodiketopiperazines. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.11.023
• 作为产物：
  描述：

  N-(Chlorosulfonyl)-exo-3-aza-4-ketotricyclo<4.2.1.0^2,5>nonane 在 盐酸 、 水 、 potassium hydrogencarbonate 、 sodium hydroxide 、 sodium sulfite 作用下， 以 水 为溶剂， 生成 (±)-cis-3-(9-fluorenylmethyloxycarbonyl)aminobicyclo[2.2.1]heptane-2-carboxylic acid
  参考文献：
  名称：

  Large-Scale Syntheses of FMOC-Protected Non-Proteogenic Amino Acids:  Useful Building Blocks for Combinatorial Libraries

  摘要：

  Convenient and reliable large-scale procedures for the protection of various amino acids with N-(9-fluorenyimethoxycarbonyl)oxysuccinimide (FMOC-OSu) are described. Commercially available 4-aminomethylbenzoic acid and trans-4-(aminomethyl)cyclohexanecarboxylic acid were converted into their corresponding FMOC-derivatives in excellent yields without the need for an extractive workup. In addition, FMOC-cis-beta -amino acids were also prepared, employing a [2 + 2]-cycloaddition strategy between a cyclic olefin and N-chlorosulfonyl isocyanate (CSI). The resulting N-chlorosulfonyl fl-lactams were reduced to the parent beta -lactams with sodium sulfite and then converted to the cis-fi-amino acid hydrochlorides by exposure to aqueous hydrochloric acid. The resulting cis-fi-amino acids were converted to their FMOC-derivatives under conditions similar to those developed for the commercially available amino acids. Differences in the conditions employed between these beta -amino acids and the commercial derivatives were observed, primarily in the nature of the base required for the reaction. A possible rationale for the differences in behavior is described. These FMOC-amino acid derivatives are valuable intermediates for the solid-phase synthesis of combinatorial libraries.

  DOI：

  10.1021/op010204f

文献信息

• Solid-phase synthesis of 6,7-cycloalkane-fused 1,4-diazepane-2,5-diones via a cyclization/release strategy
  作者：Jurgen Caroen、An Clemmen、Judit Kámán、Fréderique Backaert、Jan L. Goeman、Ferenc Fülöp、Johan Van der Eycken

  DOI：10.1016/j.tet.2015.11.023

  日期：2016.1

  A solid-phase synthesis procedure for the parallel preparation of 6,7-cycloalkane-fused 1,4-diazepane-2,5-diones is described. The methodology applies alpha- and alicyclic beta-amino acid building blocks to construct the seven-membered heterocyclic core, while alcohols are used for further skeletal decoration. The use of a cyclization/release strategy permits the isolation of the target cyclic alpha,beta-dipeptides in good crude purities and generally moderate to good yields. A 26-membered model library is reported and NMR spectroscopical data are used to describe the overall conformational behaviour of the obtained homodiketopiperazines. (C) 2015 Elsevier Ltd. All rights reserved.
• Large-Scale Syntheses of FMOC-Protected Non-Proteogenic Amino Acids:  Useful Building Blocks for Combinatorial Libraries
  作者：Jeffrey M. Dener、Pascal P. Fantauzzi、Tushar A. Kshirsagar、Daphne E. Kelly、Aaron B. Wolfe

  DOI：10.1021/op010204f

  日期：2001.7.1

  Convenient and reliable large-scale procedures for the protection of various amino acids with N-(9-fluorenyimethoxycarbonyl)oxysuccinimide (FMOC-OSu) are described. Commercially available 4-aminomethylbenzoic acid and trans-4-(aminomethyl)cyclohexanecarboxylic acid were converted into their corresponding FMOC-derivatives in excellent yields without the need for an extractive workup. In addition, FMOC-cis-beta -amino acids were also prepared, employing a [2 + 2]-cycloaddition strategy between a cyclic olefin and N-chlorosulfonyl isocyanate (CSI). The resulting N-chlorosulfonyl fl-lactams were reduced to the parent beta -lactams with sodium sulfite and then converted to the cis-fi-amino acid hydrochlorides by exposure to aqueous hydrochloric acid. The resulting cis-fi-amino acids were converted to their FMOC-derivatives under conditions similar to those developed for the commercially available amino acids. Differences in the conditions employed between these beta -amino acids and the commercial derivatives were observed, primarily in the nature of the base required for the reaction. A possible rationale for the differences in behavior is described. These FMOC-amino acid derivatives are valuable intermediates for the solid-phase synthesis of combinatorial libraries.