1-(2-碘苯基)萘-2-醇 | 142095-76-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-(2-碘苯基)萘-2-醇
• 英文名称: 1-(2-iodophenyl)-2-naphthol
• 英文别名: 1-(2-iodophenyl)naphthalen-2-ol
• CAS: 142095-76-9
• 化学式: C₁₆H₁₁IO
• 分子量: 346.167
• InChiKey: SPCAAKADSHORAW-UHFFFAOYSA-N

物化性质

• 沸点：
  430.8±33.0 °C(Predicted)
• 密度：
  1.653±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-碘苯基)萘-2-醇 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-甲氧基-1-萘基硼酸 在 四(三苯基膦)钯 、 三溴化硼 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 96.0h， 生成 1-(2-碘苯基)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

• Sigmatropic Rearrangements of Hypervalent‐Iodine‐Tethered Intermediates for the Synthesis of Biaryls
  作者：Mitsuki Hori、Jing‐Dong Guo、Tomoyuki Yanagi、Keisuke Nogi、Takahiro Sasamori、Hideki Yorimitsu

  DOI：10.1002/anie.201801132

  日期：2018.4.16

  dehydrogenative couplings of aryliodanes with phenols to afford 2‐hydroxy‐2′‐iodobiaryls have been developed. This reaction proceeds through ligand exchange on the hypervalent iodine atom followed by a [3,3] sigmatropic rearrangement and with complete regioselectivity. This coupling, in combination with in situ oxidation by mCPBA, enables the convenient conversion of iodoarenes into desirable biaryls. The

  已开发了芳金属芳烃与苯酚的无金属脱氢偶联反应，可制得2-羟基-2'-碘联芳基。该反应通过高价碘原子上的配体交换进行，然后进行[3,3]σ重排，并具有完全的区域选择性。这种耦合，结合在原位氧化由米CPBA使碘代芳烃方便地转化为所需的联芳基。所获得的联芳基在附近具有可转换的碘基和羟基，因此可用于合成，如π延伸的呋喃和取代的[5]螺旋烯的受控合成所举例说明的。DFT计算清楚地表明，重排是σ向性的，CC键的形成和IO键的断裂均以协调的方式进行。乙酸是该方案的最佳溶剂，它使碘原子更具阳离子性，从而加速了σ重排。
• 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。
• 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。