N-Methallyl-1-naphthamide | 141363-11-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-Methallyl-1-naphthamide
• 英文别名: N-(2-methylallyl)-1-naphthamide；1-Naphthamide, N-methallyl-；N-(2-methylprop-2-enyl)naphthalene-1-carboxamide
• CAS: 141363-11-3
• 化学式: C₁₅H₁₅NO
• 分子量: 225.29
• InChiKey: XFUUMIYFBOSMQN-UHFFFAOYSA-N

物化性质

• 沸点：
  441.4±24.0 °C(Predicted)
• 密度：
  1.081±0.06 g/cm3(Predicted)
• 保留指数：
  2229

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  二苯基二硒醚 、 N-Methallyl-1-naphthamide 在 2,4,5,6-四(9H-咔唑-9-基)异酞腈 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以97%的产率得到5-methyl-2-(naphthalen-1-yl)-5-((phenylselanyl)methyl)-4,5-dihydrooxazole
  参考文献：
  名称：

  Preparation of Heterocycles via Visible-Light-Driven Aerobic Selenation of Olefins with Diselenides

  摘要：

  The aerobic dehydrogenative cyclization of alkenes with easily accessible diselenides facilitated by visible light is reported. Notably, the features of this transition-metal-free protocol are pronounced efficiency and practicality, good functional group tolerance, atom economy, and high sustainability, since ambient air and visible light are adequate for the clean construction of five- and six membered heterocycles in yields of up to 98%.

  DOI：

  10.1021/acs.orglett.8b03738
• 作为产物：
  描述：

  1-萘甲酰氯 、 2-甲基烯丙基胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-Methallyl-1-naphthamide
  参考文献：
  名称：

  Preparation of Heterocycles via Visible-Light-Driven Aerobic Selenation of Olefins with Diselenides

  摘要：

  The aerobic dehydrogenative cyclization of alkenes with easily accessible diselenides facilitated by visible light is reported. Notably, the features of this transition-metal-free protocol are pronounced efficiency and practicality, good functional group tolerance, atom economy, and high sustainability, since ambient air and visible light are adequate for the clean construction of five- and six membered heterocycles in yields of up to 98%.

  DOI：

  10.1021/acs.orglett.8b03738

文献信息

• Acylated 2,2-dimethylaziridines: regioselectivity of ring opening by sodium thiophenolate; borderline SN2 due to planarization of nitrogen pyramid
  作者：Pen-yuan Lin、Konstantinos Bellos、Helmut Stamm、Andreas Onistschenko

  DOI：10.1016/s0040-4020(01)88757-3

  日期：1992.3

  carrying a COR group on nitrogen are opened by PhS⊖ with a regioselectivity RS = abnormal:normal ⩾ 20 in MeOH and 5–16 in THF. Practically no influence of COR on RS was found except for the poorest oxidant 1g (R = tBu) that gave the highest RS (95, MeOH). This rules out an SET mechanism for the abnormal opening. Absence of homolytic ring opening is directly shown by the failure to detect products resulting

  2,2- Dimethylaziridines 1正常⩾20在MeOH和5-16在THF：承载上氮COR基团通过PhS⊖具有区域选择性RS =异常打开。几乎没有发现COR对RS的影响，除了最差的氧化剂1g（R = tBu）给出了最高的RS（95，MeOH）。这排除了用于异常打开的SET机制。当COR为肉桂酰基（1f）时，没有检测到由均溶形成的自由基环化产生的产物，可以直接证明没有均溶的开环。当位阻增加时（N-苯甲酰基氮丙啶13），任何与PhS 6的反应的抑制都表明了直接的亲核攻击。观察到的S N 2的边界行为为1通过反应不良的1的扁平氮构型的反应来解释。在这种（几乎）平面构象中的羧酰胺共振在N上产生大量正电荷，通过在被PhS 4攻击之前，N-CMe 2键的部分杂化，该机理将更接近S N 1 。
• Preparation of Heterocycles via Visible-Light-Driven Aerobic Selenation of Olefins with Diselenides
  作者：Qing-Bao Zhang、Pan-Feng Yuan、Liang-Lin Kai、Kai Liu、Yong-Liang Ban、Xue-Yang Wang、Li-Zhu Wu、Qiang Liu

  DOI：10.1021/acs.orglett.8b03738

  日期：2019.2.15

  The aerobic dehydrogenative cyclization of alkenes with easily accessible diselenides facilitated by visible light is reported. Notably, the features of this transition-metal-free protocol are pronounced efficiency and practicality, good functional group tolerance, atom economy, and high sustainability, since ambient air and visible light are adequate for the clean construction of five- and six membered heterocycles in yields of up to 98%.