1-bromo-1-fluoro-2-hexylcyclopropane | 155852-62-3

• 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-bromo-1-fluoro-2-hexylcyclopropane
• 英文别名: 1-Bromo-1-fluoro-2-hexylcyclopropane
• CAS: 155852-62-3
• 化学式: C₉H₁₆BrF
• 分子量: 223.128
• InChiKey: KAWVTOPTTXVFHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  1.0
• 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-bromo-1-fluoro-2-hexylcyclopropane 在 nitrosonium tetrafluoroborate 、 三氯化磷 作用下， 以 氯仿 为溶剂， 反应 2.0h， 生成 4-fluoro-6-hexyl-2-methylpyrimidine
  参考文献：
  名称：

  一种新颖有效的4-氟嘧啶方法

  摘要：

  在各种还原条件下，研究了通过三组分杂环化获得的一系列4-氟嘧啶-1-氧化物。阐述了从容易获得的起始原料合成4-氟嘧啶的有效制备方法。已证明4-氟取代的四氢喹唑啉和四氢喹唑啉N-氧化物在芳族亲核取代中具有高反应性。

  DOI：

  10.1016/j.tetlet.2013.11.070
• 作为产物：
  描述：

  二溴氟甲烷 、 辛烯 在 苄基三乙基氯化铵 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 72.0h， 以74%的产率得到1-bromo-1-fluoro-2-hexylcyclopropane
  参考文献：
  名称：

  Three-Component Heterocyclization of gem-Bromofluorocyclopropanes with NOBF₄: Access to 4-Fluoropyrimidine N-Oxides

  摘要：

  Novel three-component heterocyclization involving gem-bromofluorocyclopropanes, nitrosyl tetrafluoroborate, and a molecule of the solvent (nitrile) yielding previously unknown fluorinated pyrimidine N-oxides is described. A two-step synthetic approach to 4-fluoropyrimidine N-oxides from alkenes under mild conditions is developed using this reaction. Mechanistic aspects of the heterocyclization are discussed.

  DOI：

  10.1021/jo301880m

文献信息

• (2-Fluoroallyl)pyridinium tetrafluoroborates: novel fluorinated electrophiles for Pd-catalyzed allylic substitution
  作者：Angelina Yu. Bobrova、Maxim A. Novikov、Yury V. Tomilov

  DOI：10.1039/d1ob00567g

  日期：——

  An efficient two-step approach to 2-fluoroallyl amines was developed that involves the synthesis of (2-fluoroallyl)pyridinium tetrafluoroborates from readily available gem-bromofluorocyclopropanes and the application of the former as novel and stable 2-fluoroallyl electrophiles for Pd-catalyzed allylic substitution.

  开发了一种有效的两步法制备 2-氟代烯丙基胺，包括从容易获得的偕溴氟环丙烷合成 (2-氟代烯丙基)吡啶鎓四氟硼酸盐，并将前者作为新型稳定的 2-氟代烯丙基亲电子试剂用于 Pd 催化的烯丙基替代。
• Synthesis of 5-fluoro- and 5-bromoalkylisoxazoles via nitrosation of 1,1-dihalocyclopropanes with sulfur trioxide activated nitrosyl chloride
  作者：Oksana B. Bondarenko、Aleksandr A. Vinogradov、Arseniy I. Komarov、Andrei S. Smirnov、Nikolai V. Zyk

  DOI：10.1016/j.jfluchem.2016.03.003

  日期：2016.5

  A method for the synthesis of 5-fluoro- and 5-bromoalkylisoxazoles via nitrosation of alkylated gem-dihalocyclopropanes with a nitrosyl chloride sulfur trioxide adduct has been developed. In the case of bromofluorocyclopropanes the reaction proceeded with excellent chemoselectivity thus providing exclusively 5-fluoroisoxazoles.

  已经开发了通过用亚硝酰氯三氧化硫加合物对烷基化的宝石-二卤代环丙烷进行亚硝化来合成5-氟-和5-溴代烷基异恶唑的方法。在溴氟环丙烷的情况下，反应以优异的化学选择性进行，因此仅提供5-氟异恶唑。
• Three-Component Heterocyclization of <i>gem</i>-Bromofluorocyclopropanes with NOBF₄: Access to 4-Fluoropyrimidine <i>N</i>-Oxides
  作者：Kseniya N. Sedenkova、Elena B. Averina、Yuri K. Grishin、Andrei G. Kutateladze、Victor B. Rybakov、Tamara S. Kuznetsova、Nikolay S. Zefirov

  DOI：10.1021/jo301880m

  日期：2012.11.2

  Novel three-component heterocyclization involving gem-bromofluorocyclopropanes, nitrosyl tetrafluoroborate, and a molecule of the solvent (nitrile) yielding previously unknown fluorinated pyrimidine N-oxides is described. A two-step synthetic approach to 4-fluoropyrimidine N-oxides from alkenes under mild conditions is developed using this reaction. Mechanistic aspects of the heterocyclization are discussed.
• A novel and effective approach to 4-fluoropyrimidines
  作者：Kseniya N. Sedenkova、Elena B. Averina、Yuri K. Grishin、Tamara S. Kuznetsova、Nikolay S. Zefirov

  DOI：10.1016/j.tetlet.2013.11.070

  日期：2014.1

  4-fluoropyrimidine 1-oxides, obtained via three-component heterocyclization, was studied under various reduction conditions. An effective preparative method for the synthesis of 4-fluoropyrimidines from readily available starting materials was elaborated. 4-Fluoro-substituted tetrahydroquinazolines and tetrahydroquinazoline N-oxides were demonstrated to be highly reactive in aromatic nucleophilic substitution.

  在各种还原条件下，研究了通过三组分杂环化获得的一系列4-氟嘧啶-1-氧化物。阐述了从容易获得的起始原料合成4-氟嘧啶的有效制备方法。已证明4-氟取代的四氢喹唑啉和四氢喹唑啉N-氧化物在芳族亲核取代中具有高反应性。