L-2-(9-fluorenyl)glycine hydrochloride | 138566-22-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: L-2-(9-fluorenyl)glycine hydrochloride
• 英文别名: (S)-9-fluorenylglycine hydrochloride；L-9-fluorenylglycine
• CAS: 138566-22-0
• 化学式: C₁₅H₁₃NO₂*ClH
• 分子量: 275.735
• InChiKey: OYJBDOAPJDRABK-UQKRIMTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.63
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  63.32
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 L-2-(9-fluorenyl)glycine hydrochloride 在 碳酸氢钠 作用下， 以 乙醇 为溶剂， 以79%的产率得到N^α-<(tert-butyloxy)carbonyl>-L-2-(9-fluorenyl)glycine
  参考文献：
  名称：

  Asymmetric synthesis of L-diphenylalanine and L-9-fluorenylglycine via room temperature alkylations of a sultam-derived glycine imine

  摘要：

  L-diphenylalanine and L-9-fluorenylglycine were prepared from a sultam-derivated glycine imine 3 via room temperature-asymmetric-alkylation/ hydrolysis/mild-sultam-clivage. The L-configuration was ascertained using an X-ray analysis of the alkylation product 4b.

  DOI：

  10.1016/0040-4039(91)80217-t
• 作为产物：
  描述：

  N-(diphenylmethylene)-L-2-(9-fluorenyl)glycinesultam 在 盐酸 、 lithium hydroxide 、 四丁基溴化铵 、 silica gel 、 lithium bromide 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 10.0h， 生成 L-2-(9-fluorenyl)glycine hydrochloride
  参考文献：
  名称：

  Asymmetric synthesis of L-diphenylalanine and L-9-fluorenylglycine via room temperature alkylations of a sultam-derived glycine imine

  摘要：

  L-diphenylalanine and L-9-fluorenylglycine were prepared from a sultam-derivated glycine imine 3 via room temperature-asymmetric-alkylation/ hydrolysis/mild-sultam-clivage. The L-configuration was ascertained using an X-ray analysis of the alkylation product 4b.

  DOI：

  10.1016/0040-4039(91)80217-t

文献信息

• Cobalt-mediated alkylation of (4R) and (4S)-3-acetoacetyl-4-benzyloxazolidin-2-ones. Preparation of enantiopure diphenylmethyl-, 9-fluorenyl- and (1-adamantyl)glycines
  作者：Nicanor Gálvez、Marcial Moreno-Mañas、Adelina Vallribera、Elies Molins、Araceli Cabrero

  DOI：10.1016/0040-4039(96)01322-6

  日期：1996.8

  The Co(II) complexes of (4R) and (4S)-3-acetoacetyl-4-benzyloxazolidin-2-ones are alkylated diastereoselectively with diphenylmethyl, 9-fluorenyl, and 1-adamantyl bromide. The resulting products are converted into enantiopure α-substituted glycines. Similar results are obtained by alkylation of the free acetoacetyloxazolidinones under Co(II)-catalysis.

  （4 R）和（4 S）-3-乙酰乙酰基-4-苄基恶唑烷丁-2-酮的Co（II）配合物被二苯甲基，9-芴基和1-金刚烷基溴化物非对映选择性地烷基化。将所得产物转化为对映体纯的α-取代的甘氨酸。在Co（II）催化下，通过将游离的乙酰乙酰基恶唑烷酮进行烷基化，可获得相似的结果。
• Design and Synthesis of Side-Chain Conformationally Restricted Phenylalanines and Their Use for Structure-Activity Studies on Tachykinin NK-1 Receptor
  作者：Hubert Josien、Solange Lavielle、Alie Brunissen、Monique Saffroy、Yvette Torrens、Jean-Claude Beaujouan、Jacques Glowinski、Gerard Chassaing

  DOI：10.1021/jm00037a009

  日期：1994.5

  Constrained analogues of phenylalanine have been conceptually designed for analyzing the binding pockets of Phe(7) (S-7) and Phe(8) (S-8), two aromatic residues important for the pharmacological properties of SP, i.e., L-tetrahydroisoquinoleic acid, L-diphenylalanine, L-9-fluorenylglycine (Flg), 2-indanylglycine, the diastereomers of L-1-indanylglycine (Ing) and L-1-benz[f]indanylglycine (Bfi), and the Z and E isomers of dehydrophenylalanine (Delta(z)Phe, Delta(E)Phe). Binding studies were performed with appropriate ligands and tissue preparations allowing the discrimination of the three tachykinin binding sites, NK-1, NK-2, and NK-3. The potencies of these agonists were evaluated in the guinea pig ileum bioassay. According to the binding data, we can conclude that the S-7 subsite is small, only the gauche (-) probe [(2S,3S)-Ing(7)]SP presents a high affinity for specific NK-1 binding sites. Surprisingly, the [Delta(E)Phe(7)]SP analogue, which projects the aromatic ring toward the trans orientation, is over 40-fold more potent than the Z isomer, [Delta(Z)Phe(7)]SP. A plausible explanation of these conflictual results Is that either the binding protein quenches the minor trans rotamer of [(2S,3S)-Ing(7)]SP in solution or this constrained amino acid side chain rotates when inserted in the protein. In position 8, the high binding affinities of [Flg(8)]SP and [(2S,3S)-Bfi(8)]SP suggest that the S-8 subsite is large enough to accept two aromatic rings in the gauche (-) and one aromatic ring in the trans direction. Peptides bearing two conformational probes in positions 7, 8, or 9 led to postulate that S-7, S-8, and S-9 subsites are independent from each other. The volumes available for side chains 7 and 8 can be estimated to be close to 110 and 240 Angstrom(3), respectively. The large volume of the S-8 subsite raises question on the localization of the SP-binding site in the NK-1 receptor. If SP were to bind in the transmembrane domains, the cleft defined by the seven transmembrane segments must rearrange during the binding process in order to bind a peptide in an ac-helical structure and at least one large binding subsite in position 8. Thus, indirect topographical analysis with constrained amino acids might contribute to the analysis of the receptor/ligand dynamics. Finally, this study demonstrates that a good knowledge of the peptidic backbone structure and a combination of constrained amino acids are prerequisites to confidently attribute the preferred orientation(s) of an amino acid side chain.