3-methylnaphtho[1,2-b]furan | 5665-38-3

• 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: 3-methylnaphtho[1,2-b]furan
• 英文别名: 3-methylbenzo[g][1]benzofuran
• CAS: 5665-38-3
• 化学式: C₁₃H₁₀O
• 分子量: 182.222
• InChiKey: VYWCUJCEUVIWID-UHFFFAOYSA-N

物化性质

• 沸点：
  76-80 °C
• 密度：
  1.162±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  1-萘酚钠 在 硫酸 作用下， 生成 3-methylnaphtho[1,2-b]furan
  参考文献：
  名称：

  Stoermer, Justus Liebigs Annalen der Chemie, 1900, vol. 312, p. 332

  摘要：

  DOI：

文献信息

• Titanium tetrachloride promoted cyclodehydration of aryloxyketones: Facile synthesis of benzofurans and naphthofurans with high regioselectivity
  作者：Qiu Zhang、Juan Luo、Bingqiao Wang、Xiaoqin Xiao、Zongjie Gan、Qiang Tang

  DOI：10.1016/j.tetlet.2019.04.020

  日期：2019.5

  An efficient and facile method for the synthesis of a broad series of benzofurans and naphthofurans is described. The direct intramolecular cyclodehydration of aryloxyketones in the presence of titanium tetrachloride affords the corresponding benzofurans and naphthofurans with good regioselectivity and yields.

  描述了一种合成广泛的苯并呋喃和萘呋喃的有效而简便的方法。在四氯化钛存在下芳氧基酮的分子内直接环脱水作用提供了相应的苯并呋喃和萘呋喃，具有良好的区域选择性和产率。
• An approach to the synthesis of naphtho[b]furans from allyl bromonaphthyl ethers employing sequential photoinduced radical cyclization and dehydrohalogenation reactions
  作者：Yusuke Suzuki、Yoshiki Okita、Toshio Morita、Yasuharu Yoshimi

  DOI：10.1016/j.tetlet.2014.04.056

  日期：2014.5

  A simple method has been developed for the efficient synthesis of naphtho[b]furans from allyl bromonaphthyl ethers. The approach utilizes a novel photochemical process involving sequential radical cyclization and dehydrohalogenation. Because light is a readily available, environmentally friendly reagent that produces no by-products, the new process serves as a green synthetic method.

  已经开发了一种从烯丙基溴萘基醚有效合成萘并[ b ]呋喃的简单方法。该方法利用了涉及顺序自由基环化和脱卤化氢的新型光化学过程。由于光是一种容易获得的，不产生副产物的环保试剂，因此新工艺可作为绿色合成方法。
• 以四氯化钛作为脱水试剂合成萘并呋喃衍生物的方法
  申请人：重庆医科大学

  公开号：CN109574967B

  公开（公告）日：2022-08-26

  本发明公开一种以萘氧基酮为原料，在四氯化钛的作用下脱水环化制备萘并呋喃衍生物的方法，即在惰性气体保护下，将α‑萘氧基酮溶于干燥的二氯甲烷，然后缓慢滴加TiCl4和二氯甲烷的混合溶液，反应结束后经分离纯化得到所述萘并呋喃衍生物。本发明所述的合成方法，原料易得，成本低廉，反应条件温和，操作简单易控，副反应较少，后处理简单，产品收率较高，大大节约了生产成本，具有较好的经济效益，适宜于工业化大生产。
• v. Kostanecki; Tambor, Chemische Berichte, 1909, vol. 42, p. 908
  作者：v. Kostanecki、Tambor

  DOI：——

  日期：——
• Hantzsch; Pfeiffer, Chemische Berichte, 1886, vol. 19, p. 1302,1303
  作者：Hantzsch、Pfeiffer

  DOI：——

  日期：——