1-溴-7-氟萘 | 13790-91-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-溴-7-氟萘
• 英文名称: 1-bromo-7-fluoronaphthalene
• 英文别名: 7-Fluor-1-brom-naphthalin
• CAS: 13790-91-5
• 化学式: C₁₀H₆BrF
• 分子量: 225.06
• InChiKey: NYNJHKLLBKIOMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2903999090

反应信息

• 作为反应物：
  描述：

  1-溴-7-氟萘 在 dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) 盐酸 、 甲醇 、 potassium carbonate 、 sodium t-butanolate 作用下， 以 甲基叔丁基醚 、 水 、 甲苯 、 乙腈 为溶剂， 反应 25.75h， 生成 2-{4-[4-(7-fluoro-naphthalen-1-yl)-piperazin-1-yl]-butoxy}-5,6,7,9-tetrahydro-1,7,9-triaza-benzocyclohepten-8-one
  参考文献：
  名称：

  WO2007/116265

  摘要：

  公开号：
• 作为产物：
  描述：

  7-fluoro-1-naphthylamine 以45%的产率得到1-溴-7-氟萘
  参考文献：
  名称：

  Synthesis of 2-fluoro-7,12-dimethylbenz[a]anthracene

  摘要：

  DOI：

  10.1021/jo01290a031

文献信息

• A Visible Light and Iron‐mediated Carbocationic Route to Polysubstituted 1‐Halonaphthalenes by Benzannulation using Allylbenzenes and Polyhalomethanes
  作者：Irwan Iskandar Roslan、Hongwei Zhang、Kian‐Hong Ng、Stephan Jaenicke、Gaik‐Khuan Chuah

  DOI：10.1002/adsc.202001249

  日期：2021.2.16

  A wide array of polysubstituted 1‐bromo and chloronaphthalenes are obtained from coupling of allylbenzenes and polyhalomethanes. The reaction is mediated by iron metal under visible light irradiation and proceeds via a Kharasch addition intermediate followed by intramolecular FeIII mediated Friedel‐Crafts alkylation, with the formation of two Csp2−Csp2 bonds in the process. This method gives easy access

  烯丙基苯与多卤代甲烷的偶联可得到各种各样的多取代的1-溴和氯萘。该反应在可见光辐射下由铁金属介导，并通过Kharasch加成中间体进行，然后进行分子内Fe III介导的Friedel-Crafts烷基化，在此过程中形成两个C sp 2 -C sp 2键。该方法可轻松获得具有C-5至C-8取代基的1-卤代萘，否则难以合成。
• Practical Synthesis of 1-(7-Fluoro-naphthalen-1-yl)piperazine Hydrochloride
  作者：Javier Magano、Anne Akin、Michael H. Chen、Kendra Giza、Jennifer Moon、James Saenz

  DOI：10.1080/00397910802179979

  日期：2008.10.22

  The original route for the synthesis of this compound involved the use of 1-amino-7-fluoronaphthalene and bis(2-chloroethyl)amine hydrochloride, two highly toxic compounds. A new protocol has been developed that employs a palladium-catalyzed Buchwald–Hartwig cross-coupling reaction between 1-Boc-piperazine and 1-bromo-7-fluoronaphthalene followed by piperazine deprotection with HCl gas. In addition

  摘要 报道了 1-(7-fluoronaphthalen-1-yl)-哌嗪盐酸盐 (1) 的实用且可扩展的制备方法。该化合物的原始合成路线涉及使用 1-氨基-7-氟萘和双（2-氯乙基）胺盐酸盐，这两种剧毒化合物。已开发出一种新方案，该方案采用钯催化的 1-Boc-哌嗪和 1-溴-7-氟萘之间的 Buchwald-Hartwig 交叉偶联反应，然后用 HCl 气体对哌嗪脱保护。此外，有效的钯去除方案允许制备含有少于 20 ppm 这种金属的目标分子。该方法已成功实施以生产多克数量的具有优异纯度和低钯含量的 1。
• Substituent Effects. VIII.¹ Synthesis of Substituted α- and β-Fluoronaphthalenes²
  作者：W. Adcock、M. J. S. Dewar

  DOI：10.1021/ja00978a038

  日期：1967.1
• The Synthesis of a Dopamine D₂ Partial Agonist for the Treatment of Schizophrenia
  作者：Javier Magano、Alison Acciacca、Anne Akin、Benjamin M. Collman、Brian Conway、Michael Waldo、Michael H. Chen、Kenneth E. Mennen

  DOI：10.1021/op800307k

  日期：2009.5.15

  The synthesis of the phosphoric acid salt of dopamine D-2 partial agonist 2-4-[4-(7-fluoro-naphthalen-1-yl)-piperazin-1-yl]-butoxy}-5,6,7,9-tetrahydro-1,7,9-triaza-benzocyclohepten-8- one (1) is reported. The most prominent feature of the molecule is a seven-membered ring urea functionality that has been prepared via an efficient one-pot, three-step transformation. The original synthesis from the Medicinal Chemistry group provided precursor 13 in 10 steps and 2% overall yield, required four chromatographies and employed unsafe reagents such as 2-iodoxybenzoic acid (IBX) and HClO4. The optimized synthetic route for the preparation of phosphate salt I consists of 12 linear steps with a 10% overall yield. Safer and more robust reaction conditions have been developed with only one required chromatography. Another key step in the synthesis is the coupling of iodide 25 with naphthalenopiperazine 12 to provide 13. Due to the difficulty to purify this intermediate, a protocol had to be developed to obtain crude material with the required purity, suitable for use in the subsequent salt formation step. Finally, considerable work was carried out to determine the most stable polymorph of the API. As a result, a robust set of conditions has been developed for the formation of phosphoric acid salt 1, providing the desired polymorph in excellent yield and purity.
• NEWMAN M. S.; TUNCAY A., J. ORG. CHEM., 1980, 45, NO 2, 348-349
  作者：NEWMAN M. S.、 TUNCAY A.

  DOI：——

  日期：——