naphtho[1,2-b]furan-3-carbaldehyde | 1065221-21-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: naphtho[1,2-b]furan-3-carbaldehyde
• 英文别名: benzo[g][1]benzofuran-3-carbaldehyde
• CAS: 1065221-21-7
• 化学式: C₁₃H₈O₂
• 分子量: 196.205
• InChiKey: FXPDHBMJNJWWBY-UHFFFAOYSA-N

物化性质

• 熔点：
  91-93 °C(Solvent: Chloroform)
• 沸点：
  366.0±15.0 °C(Predicted)
• 密度：
  1.289±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  naphtho[1,2-b]furan-3-carbaldehyde 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以74%的产率得到naphtho[1,2-b]furan-3-ylmethanol
  参考文献：
  名称：

  Structure−Activity Relationships for a Novel Series of Dopamine D2-like Receptor Ligands Based on N-Substituted 3-Aryl-8-azabicyclo[3.2.1]octan-3-ol

  摘要：

  Discovering dopamine D2-like receptor subtype-selective ligands has been a focus of significant investigation. The D2R-selective antagonist 3-[4-(4-chlorophenyl)-4-hydroxypiperidinyl]methylindole (1, L741,626; K-i(D2R/MR) = 11.2:163 nM) has previously provided a lead template for chemical modification. Herein, analogues have been synthesized where the piperidine was replaced by a tropane ring that reversed the selectivity seen in the parent compound, in human hD2(L)R- or hD3R-transfected HEK 293 cells (31, K-i(D2R/D3R) = 33.4: 15.5 nM). Further exploration of both N-substituted and aryl ring-substituted analogues resulted in the discovery of several high affinity D2R/D3R ligands with 3-benzofurylmethyl-substituents (e.g., 45, K-i(D2R/D3R) = 1.7:0.34 nM) that induced high affinity not achieved in similarly N-substituted piperidine analogues and significantly (470-fold) improved D3R binding affinity compared to the parent ligand 1. X-ray crystallographic data revealed a distinctive spatial arrangement of pharmacophoric elements in the piperidinol vs tropine analogues, providing clues for the diversity in SAR at the D2 and D3 receptor subtypes.

  DOI：

  10.1021/jm800532x
• 作为产物：
  描述：

  3-methylnaphtho[1,2-b]furan 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.0h， 以77%的产率得到naphtho[1,2-b]furan-3-carbaldehyde
  参考文献：
  名称：

  Structure−Activity Relationships for a Novel Series of Dopamine D2-like Receptor Ligands Based on N-Substituted 3-Aryl-8-azabicyclo[3.2.1]octan-3-ol

  摘要：

  Discovering dopamine D2-like receptor subtype-selective ligands has been a focus of significant investigation. The D2R-selective antagonist 3-[4-(4-chlorophenyl)-4-hydroxypiperidinyl]methylindole (1, L741,626; K-i(D2R/MR) = 11.2:163 nM) has previously provided a lead template for chemical modification. Herein, analogues have been synthesized where the piperidine was replaced by a tropane ring that reversed the selectivity seen in the parent compound, in human hD2(L)R- or hD3R-transfected HEK 293 cells (31, K-i(D2R/D3R) = 33.4: 15.5 nM). Further exploration of both N-substituted and aryl ring-substituted analogues resulted in the discovery of several high affinity D2R/D3R ligands with 3-benzofurylmethyl-substituents (e.g., 45, K-i(D2R/D3R) = 1.7:0.34 nM) that induced high affinity not achieved in similarly N-substituted piperidine analogues and significantly (470-fold) improved D3R binding affinity compared to the parent ligand 1. X-ray crystallographic data revealed a distinctive spatial arrangement of pharmacophoric elements in the piperidinol vs tropine analogues, providing clues for the diversity in SAR at the D2 and D3 receptor subtypes.

  DOI：

  10.1021/jm800532x

文献信息

• Ru(II)-Catalyzed C–H Activation/Alkylation of 3-Formylbenzofurans with Conjugated Olefins: Product Divergence
  作者：Kolluru Srinivas、Shaziyaparveen K. Siddiqui、Jyothi K. Mudaliar、Chepuri V. Ramana

  DOI：10.1021/acs.joc.8b03267

  日期：2019.5.3

  Ru-catalyzed alkylation of 3-formylbenzofuran with acrylates and acrylamides has been described. Branched selectivity with unsubstituted or β-substituted acrylates/acrylamides and linear selectivity with α-substituted acrylates have been observed. However, in all of the cases, the intermediate alkylation products seem to undergo further reactions, either cycloannulation or deformylation, depending

  已经描述了Ru用丙烯酸酯和丙烯酰胺催化3-甲酰基苯并呋喃的烷基化。已经观察到与未取代的或β-取代的丙烯酸酯/丙烯酰胺的支链选择性和与α-取代的丙烯酸酯的线性选择性。然而，在所有情况下，取决于所用的底物，中间烷基化产物似乎都经历了进一步的反应，无论是环环化还是甲酰基化。例如，对于丙烯酸甲酯，中间支化的烷基化产物与另一个丙烯酸甲酯分子进行环环化，从而导致致密地官能化的环己烯环的形成。另一方面，在N-单取代的丙烯酰胺的情况下，支链烷基化会随着分子内的醛-酰胺缩合而进行，从而导致吡啶-2-酮环化。然而，