1-benzindanyl bromide | 146000-51-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-benzindanyl bromide
• 英文别名: 1-bromobenzindan；1-bromobenz[f]indane；3-bromo-2,3-dihydro-1H-cyclopenta[b]naphthalene
• CAS: 146000-51-3
• 化学式: C₁₃H₁₁Br
• 分子量: 247.134
• InChiKey: GRXIWUBYMIIEGT-UHFFFAOYSA-N

物化性质

• 沸点：
  347.2±21.0 °C(Predicted)
• 密度：
  1.479±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-benzindanyl bromide 在 盐酸 、 六甲基磷酰三胺 、 sodium sulfide 、 正丁基锂 、 碳酸氢钠 、 methyloxirane 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 氯仿 为溶剂， 反应 48.0h， 生成 N^α-<(tert-butyloxy)carbonyl>-(2S,3S)-2-(1-benzindanyl)glycine
  参考文献：
  名称：

  Asymmetric synthesis of the diastereoisomers of L-1-indanylglycine and L-1-benz[f]indanylglycine, χ1,χ2-constrained side-chain derivatives of L-phenylalanine and L-2-naphthylalanine

  摘要：

  The diastereoisomers of L-1-indanylglycine and L-1-benz[f]indanylglycine, novel topographic tools and anologues of phenylalanine and 2-naphtylalanine, were synthesized from a sultam-derived glycine imine synthon alkylated by judicious electrophiles, and subsequent hydrolysis and sultam-cleavage. An X-ray analysis on one alkylation product established the beta-configuration.

  DOI：

  10.1016/0957-4166(92)80003-f
• 作为产物：
  描述：

  2,3-二氢-1H-环戊二烯并[b]萘-1-醇 在 吡啶 、 三溴化磷 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以89%的产率得到1-benzindanyl bromide
  参考文献：
  名称：

  Catalytic Enantioselective Negishi Reactions of Racemic Secondary Benzylic Halides

  摘要：

  This report describes the first enantioselective cross-couplings of racemic secondary benzylic halides, specifically, nickel-catalyzed Negishi reactions of bromides and chlorides. The catalyst components are commercially available and air-stable, and the reaction is not highly oxygen- or moisture-sensitive (it can be set up in the air). The method has been applied to the catalytic enantioselective synthesis of intermediates employed by others in the generation of bioactive compounds (e.g., trikentrin A and an androgen receptor agonist).

  DOI：

  10.1021/ja053751f

文献信息

• 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.