tert-butyl (2-fluoro-1-phenylethyl)carbamate | 2006278-27-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl (2-fluoro-1-phenylethyl)carbamate
• 英文别名: N-Boc-2-fluoro-1-phenylethanamine；tert-butyl N-(2-fluoro-1-phenylethyl)carbamate
• CAS: 2006278-27-7
• 化学式: C₁₃H₁₈FNO₂
• 分子量: 239.29
• InChiKey: URSFJYUZIMUYRH-UHFFFAOYSA-N

物化性质

• 沸点：
  338.8±37.0 °C(Predicted)
• 密度：
  1.071±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  氟碘甲烷 、 benzaldehyde N-boc imine 在 methyllithium lithium bromide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.08h， 以92%的产率得到tert-butyl (2-fluoro-1-phenylethyl)carbamate
  参考文献：
  名称：

  Exploiting a “Beast” in Carbenoid Chemistry: Development of a Straightforward Direct Nucleophilic Fluoromethylation Strategy

  摘要：

  The first direct and straightforward nucleophilic fluoromethylation of organic compounds is reported. The tactic employs a "fleeting" lithium fluorocarbenoid (LiCH2F) generated from commercially available fluoroiodomethane. Precise reaction conditions were developed for the generation and synthetic exploitation of such a labile species. The versatility of the strategy is showcased in ca. 50 examples involving a plethora of electrophiles. Highly valuable chemicals such as fluoroalcohols, fluoroamines, and fluoromethylated oxygenated heterocycles could: be prepared in very good yields through a single synthetic operation. The scalability of the reaction and its application to complex molecular architectures (e.g., steroids) are documented.

  DOI：

  10.1021/jacs.7b07891