1-(2-溴苯基)萘-2-醇 | 142095-77-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-(2-溴苯基)萘-2-醇
• 英文名称: 1-(2-bromophenyl)-2-naphthol
• 英文别名: 1-(2-bromophenyl)naphthalen-2-ol
• CAS: 142095-77-0
• 化学式: C₁₆H₁₁BrO
• 分子量: 299.167
• InChiKey: ITKPOSOKSSEUKQ-UHFFFAOYSA-N

物化性质

• 沸点：
  400.0±25.0 °C(Predicted)
• 密度：
  1.470±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-溴苯基)萘-2-醇 在 正丁基锂 、 [RhCl2(p-cymene)]2 、 copper diacetate 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 乙醚 、 正己烷 为溶剂， 反应 7.25h， 生成
  参考文献：
  名称：

  通过 C(sp2)-H 键活化方法 RuII 催化萘酚的乙烯基脱芳构化

  摘要：

  1-芳基-2-萘酚与内部炔烃的分子间环化反应在Ru催化剂和Cu氧化剂的存在下有效进行，通过C(sp(2))-H键的连续裂解、迁移插入生成螺环化合物炔烃和萘环的脱芳构化。通过这种新方法可以获得具有全碳四元立体中心的各种螺环分子，具有良好的产率和出色的区域选择性，并且目前的方法可以耐受各种合成重要的官能团。

  DOI：

  10.1021/ja410060e
• 作为产物：
  描述：

  1-(2-bromophenyl)-2-methoxynaphthalene 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以0.42 g的产率得到1-(2-溴苯基)萘-2-醇
  参考文献：
  名称：

  Pd(0)-catalyzed chemoselective construction of spirocarbocycles via an alkyne insertion/β-naphthol dearomatization cascade

  摘要：

  通过微波辅助Pd(0)催化的炔烃迁移插入/β-萘酚脱芳构联烯级联反应，实现了一种高度化学选择性的制备螺[茚-1,1'-萘]-2'-酮的途径。

  DOI：

  10.1039/c4cc09099c

文献信息

• The reactivity of oxygen nucleophiles with aryl radicals in the SRN1 mechanism
  作者：María T. Baumgartner、Adriana B. Pierini、Robert A. Rossi

  DOI：10.1016/s0040-4039(00)74201-8

  日期：1992.4

  The photostimulated reaction of 2-naphthoxide ions 1 with o-dihalobenzenes in liquid ammonia gives the halosubstituted product 4 and the cyclized substituted product 5. This is the first report about the coupling of an aromatic σ radical with an oxygen functionality in the chain propagation cycle of the SRN1 mechanism.

  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。
• Palladium-Catalyzed Dynamic Kinetic Asymmetric Transformation of Racemic Biaryls: Axial-to-Central Chirality Transfer
  作者：Liu Yang、Huayu Zheng、Lei Luo、Jiang Nan、Jingjing Liu、Yaoyu Wang、Xinjun Luan

  DOI：10.1021/jacs.5b01285

  日期：2015.4.22

  The first dynamic kinetic asymmetric transformation of racemic biaryl substrates on the basis of axial-to-central chirality transfer has been realized. Chiral Pd-NHC complexes were found to catalyze the dynamic kinetic asymmetric spiroannulation of 4-(2-bromoaryl)-naphthalen-1-ols (or 2'-bromo-[1,1'-biphenyl]-4-ols) with internal alkynes, affording a series of enantioenriched spirocyclic products bearing an all-carbon quaternary stereocenter in good yields (up to 95%) with excellent enantioselectivities (up to 97% ee).
• 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.
• Pd(0)-catalyzed chemoselective construction of spirocarbocycles via an alkyne insertion/β-naphthol dearomatization cascade
  作者：Huayu Zheng、Lu Bai、Jingjing Liu、Jiang Nan、Zhijun Zuo、Liu Yang、Yaoyu Wang、Xinjun Luan

  DOI：10.1039/c4cc09099c

  日期：——

  A highly chemoselective route to obtain spiro[indene-1,1′-naphthalen]-2′-ones via a microwave-assisted Pd(0)-catalyzed alkyne migratory insertion/β-naphthol dearomatization cascade is described.

  通过微波辅助Pd(0)催化的炔烃迁移插入/β-萘酚脱芳构联烯级联反应，实现了一种高度化学选择性的制备螺[茚-1,1'-萘]-2'-酮的途径。
• Ru^II-Catalyzed Vinylative Dearomatization of Naphthols via a C(sp²)–H Bond Activation Approach
  作者：Jiang Nan、Zhijun Zuo、Lei Luo、Lu Bai、Huayu Zheng、Yini Yuan、Jingjing Liu、Xinjun Luan、Yaoyu Wang

  DOI：10.1021/ja410060e

  日期：2013.11.20

  by sequential cleavage of the C(sp(2))-H bond, migratory insertion of the alkyne, and dearomatization of the naphthyl ring. Various spirocyclic molecules bearing an all-carbon quaternary stereocenter could be obtained by this novel method with good yields and excellent regioselectivity, and the current process tolerates a variety of synthetically important functional groups.

  1-芳基-2-萘酚与内部炔烃的分子间环化反应在Ru催化剂和Cu氧化剂的存在下有效进行，通过C(sp(2))-H键的连续裂解、迁移插入生成螺环化合物炔烃和萘环的脱芳构化。通过这种新方法可以获得具有全碳四元立体中心的各种螺环分子，具有良好的产率和出色的区域选择性，并且目前的方法可以耐受各种合成重要的官能团。