1-Fluoro-3-bromoadamantane | 60389-54-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氟化物
• 英文名称: 1-Fluoro-3-bromoadamantane
• 英文别名: 1-bromo-3-fluoroadamantane；1-Bromo-3-fluoradamantan；1-Fluor-3-brom-adamantan；1-Fluor-3-bromadamantan
• CAS: 60389-54-0
• 化学式: C₁₀H₁₄BrF
• 分子量: 233.124
• InChiKey: ZGCQRAFVAQLBCH-UHFFFAOYSA-N

物化性质

• 沸点：
  241.9±23.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-Fluoro-3-bromoadamantane 在 偶氮二异丁腈 、 氘代三正丁基锡 作用下， 以90%的产率得到
  参考文献：
  名称：

  Transmission of polar substituent effects in saturated systems: synthesis and fluorine-19 NMR study of 3-substituted adamant-1-yl fluorides

  摘要：

  DOI：

  10.1021/jo00379a008
• 作为产物：
  描述：

  1-氟金刚烷 在 三氯溴甲烷 作用下， 生成 1-Fluoro-3-bromoadamantane
  参考文献：
  名称：

  Perkins,R.R.; Pincock,R.E., Canadian Journal of Chemistry, 1978, vol. 56, p. 1269 - 1272

  摘要：

  DOI：

文献信息

• eFluorination Using Cheap and Readily Available Tetrafluoroborate Salts
  作者：Matthew C. Leech、Dmitrii Nagornîi、Jamie M. Walsh、Cyrille Kiaku、Darren L. Poole、Joseph Mason、Iain C. A. Goodall、Perry Devo、Kevin Lam

  DOI：10.1021/acs.orglett.2c04305

  日期：2023.3.10

  synthesis of tertiary hindered alkyl fluorides from carboxylic acids has been developed without the need for hydrofluoric acid salts or non-glass reactors. In this anodic fluorination, collidinium tetrafluoroborate acts as both the supporting electrolyte and fluoride donor. A wide range of functional groups has been shown to be compatible, and the possibility of scale-up using flow electrochemistry has also

  已经开发出一种实用的电化学方法，用于从羧酸快速、安全和温和地合成叔受阻烷基氟化物，而无需氢氟酸盐或非玻璃反应器。在这种阳极氟化反应中，四氟硼酸可力丁作为支持电解质和氟化物供体。广泛的官能团已被证明是相容的，并且还证明了使用流式电化学进行放大的可能性。
• Bolte, Gerd; Haas, Alois, Chemische Berichte, 1984, vol. 117, # 5, p. 1982 - 1986
  作者：Bolte, Gerd、Haas, Alois

  DOI：——

  日期：——
• Mechanistic definition of trimethylstannylation of 1,3-dihaloadamantanes: delocalized radical anions as possible intermediates
  作者：William Adcock、Christopher I. Clark

  DOI：10.1021/jo00078a009

  日期：1993.12

  A series of 1,3-dihaloadamantanes (3, X = Y = halogens) have been synthesized, characterized, and treated with (trimethylstannyl) alkali reagents (Me3SnM, M = Li or Na) in the absence and presence of tert-butylamine (TBA) and dicyclohexylphosphine (DCPH). The product distributions of these reactions have been established by C-13 and Sn-119 NMR spectroscopy and vapor-phase chromatographic analyses. Tin substitution via an S(RN)1-type pathway is shown to be a significant reaction for several of the derivatives of 3 (X = F, Y Br or I; X = Cl, Y = Br or I; X = Y = Br) but not for the bromo iodide or diiodide (3, X = Br, Y = I and X = Y = I). For the latter two compounds, the formation of 1,3-dehydroadamantane or propellane 8 is the predominant reaction product while tin substitution is insignificant. Propellane 8 formation is also a significant reaction product for some of the other dihalo derivatives of 3 (X = Cl, Y = I and X = Y = Br) but not for others (3, X = F, Y = Br or I and X = Cl, Y = Br). The mechanism of formation of 8 is perplexing in light of the trapping experiments in the presence of TBA and DCPH. A possible pathway is proposed in which the key intermediate is a delocalized radical anion.
• Perkins,R.R.; Pincock,R.E., Canadian Journal of Chemistry, 1978, vol. 56, p. 1269 - 1272
  作者：Perkins,R.R.、Pincock,R.E.

  DOI：——

  日期：——
• Transmission of polar substituent effects in saturated systems: synthesis and fluorine-19 NMR study of 3-substituted adamant-1-yl fluorides
  作者：William Adcock、Gaik B. Kok

  DOI：10.1021/jo00379a008

  日期：1987.2