1-(2-氯苯基)-2-萘酚 | 142095-78-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-(2-氯苯基)-2-萘酚
• 英文名称: 1-(2-chlorophenyl)-2-naphthol
• 英文别名: 1-(2-Chlorophenyl)naphthalen-2-ol
• CAS: 142095-78-1
• 化学式: C₁₆H₁₁ClO
• 分子量: 254.716
• InChiKey: BONMAWCZPKHWBO-UHFFFAOYSA-N

物化性质

• 沸点：
  379.6±22.0 °C(Predicted)
• 密度：
  1.278±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  18
• 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：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(2-氯苯基)-2-萘酚 在 乙醇 、 sodium 作用下， 生成 苯并[b]萘并[1,2-d]呋喃
  参考文献：
  名称：

  S RN 1机理中氧亲核试剂与芳基的反应性

  摘要：

  2-萘氧基离子1与邻二卤代苯在液态氨中的光刺激反应得到卤代产物4和环化取代产物5。这是关于在S RN 1机理的链传播循环中芳族σ自由基与氧官能团偶联的第一个报道。

  DOI：

  10.1016/s0040-4039(00)74201-8
• 作为产物：
  描述：

  2-溴氯苯 、 2-naphtholate 在 potassium tert-butylate 作用下， 以 氨 为溶剂， 反应 3.0h， 以17%的产率得到1-(2-氯苯基)-2-萘酚
  参考文献：
  名称：

  S RN 1机理中氧亲核试剂与芳基的反应性

  摘要：

  2-萘氧基离子1与邻二卤代苯在液态氨中的光刺激反应得到卤代产物4和环化取代产物5。这是关于在S RN 1机理的链传播循环中芳族σ自由基与氧官能团偶联的第一个报道。

  DOI：

  10.1016/s0040-4039(00)74201-8

文献信息

• Diversification of Naphthol Skeletons Triggered by Aminative Dearomatization
  作者：Linqiang Li、Dong Wang、Yue Zhang、Jingjing Liu、Han Wang、Xinjun Luan

  DOI：10.1021/acs.orglett.4c01416

  日期：2024.6.14

  including ring expansion, ring opening, ring contraction, and atom transmutation of aryl scaffolds. This approach enables the synthesis of a diverse array of azepinones, unsaturated amides, isoquinolines, and indenones from naphthol substrates. Its application in the synthesis of bioactive and functional molecules as well as the conversion of complex molecular skeletons underscores its broad potential applicability

  银催化的萘酚氨基脱芳构化反应已被开发出来，并整合到逐步的方法中，用于随后的骨架多样化，包括扩环、开环、收缩和芳基支架的原子嬗变。这种方法能够从萘酚底物合成多种氮杂酮、不饱和酰胺、异喹啉和茚酮。其在生物活性和功能分子的合成以及复杂分子骨架的转化中的应用强调了其广泛的潜在适用性。机理研究表明脱芳构化中间体的中间作用。
• Photostimulated reactions of o-dihalobenzenes with nucleophiles derived from the 2-naphthyl system. Competition between electron transfer, fragmentation, and ring closure reactions
  作者：Maria T. Baumgartner、Adriana B. Pierini、Roberto A. Rossi

  DOI：10.1021/jo00061a040

  日期：1993.4

  The photostimulated reaction of o-dihalobenzenes 2 with 2 naphthoxide ions 1-O gave the substitution product on carbon 1 of the naphthyl moiety with retention of halogen (1, Br, and Cl) 3 as well as the ring closure product benzo[b]naphtho[1,2-d]furan (4), with product 3 being an intermediate in the formation of 4. The products obtained in the photostimulated reaction of 2-naphthalenethiolate ions 1-S with 2 depend on the halogens. When both nucleofugal groups are iodine, only the ring closure product benzo[b]naphtho[1,2-d]thiophene (10) is obtained. With o-bromoiodobenzene, the photostimulated reaction gave 10 and the substitution product on sulfur with retention of bromine, while with o-chloroiodobenzene the only observed product was the substitution product on sulfur with retention of chlorine. The photostimulated reaction of 2 with 2-naphthaleneselenolate ions 1-Se gave the same amount of cyclized product benzo[b]naphtho[1,2-d]selenophene (14) and the substitution product on selenium without retention of halogen 15, although in an overall low yield. It is suggested that all these reactions occur by the S(RN)1 mechanism. Theoretical studies support the different behavior found with the nucleophiles derived from the 2-naphthyl system.