2-fluoro-6-(3-phenyl-1-(prop-1-en-2-yl)cyclobutoxy)pyridine | 1345831-08-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-fluoro-6-(3-phenyl-1-(prop-1-en-2-yl)cyclobutoxy)pyridine
• 英文别名: 2-Fluoro-6-(3-phenyl-1-prop-1-en-2-ylcyclobutyl)oxypyridine
• CAS: 1345831-08-4
• 化学式: C₁₈H₁₈FNO
• 分子量: 283.345
• InChiKey: SGAPJKJZKJAZME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  O-ethyl S-(2-((8S,9S,10R,13S,14S,17R)-17-hydroxy-10,13-dimethyl-3,11-dioxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl) carbonodithioate 、 2-fluoro-6-(3-phenyl-1-(prop-1-en-2-yl)cyclobutoxy)pyridine 在 过氧化双月桂酰 作用下， 以 1,1-二氯乙烷 、 乙酸乙酯 为溶剂， 反应 0.25h， 以60%的产率得到(8S,9S,10R,13S,14S,17R)-17-hydroxy-10,13-dimethyl-17-(4-(3-phenylcyclobutylidene)pentanoyl)-7,8,9,10,12,13,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-3,11(2H,6H)-dione
  参考文献：
  名称：

  Elimination versus Ring Opening: A Convergent Route to Alkylidene-Cyclobutanes

  摘要：

  Functionalized alkylidene-cyclobutanes have been prepared from 2-fluoropyridinyl-6-oxy precursors derived from vinyl cyclobutanols by a radical addition elimination process. A wide range of functional groups is tolerated, and the alkylidene-cyclobutanes can be further elaborated Into cyclopentanones. The limitation of this approach resides in the competition with opening of the cyclobutane ring.

  DOI：

  10.1021/ol202798r
• 作为产物：
  描述：

  3-苯基环丁酮 在 sodium hydride 作用下， 以 四氢呋喃 、 二甲基亚砜 、 mineral oil 为溶剂， 反应 0.5h， 生成 2-fluoro-6-(3-phenyl-1-(prop-1-en-2-yl)cyclobutoxy)pyridine
  参考文献：
  名称：

  Elimination versus Ring Opening: A Convergent Route to Alkylidene-Cyclobutanes

  摘要：

  Functionalized alkylidene-cyclobutanes have been prepared from 2-fluoropyridinyl-6-oxy precursors derived from vinyl cyclobutanols by a radical addition elimination process. A wide range of functional groups is tolerated, and the alkylidene-cyclobutanes can be further elaborated Into cyclopentanones. The limitation of this approach resides in the competition with opening of the cyclobutane ring.

  DOI：

  10.1021/ol202798r

文献信息

• Radical-Based Route to 2-(Trifluoromethyl)-1,3,4-oxadiazoles and Trifluoromethyl-Substituted Polycyclic 1,2,4-Triazoles and Dihydrofurans
  作者：Ling Qin、Samir Z. Zard

  DOI：10.1021/acs.orglett.5b00457

  日期：2015.3.20

  O-Ethyl S-[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]methyl xanthate was readily prepared on a large scale and shown to undergo very efficient intermolecular radical additions to unactivated alkenes. The products were further elaborated by exploiting both radical and ionic processes to provide a variety of trifluoromethyl-substituted derivatives, including medicinally relevant triazoles. In particular, the application of a radical allylation on the initial adducts leads to structures that are able to undergo intramolecular [4 + 2] cycloaddition reactions.