Benzyl 2-(2-oxatricyclo[6.3.1.04,12]dodeca-1(11),4,6,8(12),9-pentaen-3-yl)acetate | 1280682-04-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Benzyl 2-(2-oxatricyclo[6.3.1.04,12]dodeca-1(11),4,6,8(12),9-pentaen-3-yl)acetate
• CAS: 1280682-04-3
• 化学式: C₂₀H₁₆O₃
• 分子量: 304.345
• InChiKey: CTGJHZIFUSLVLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  萘酚 、 丙烯酸苄酯 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 copper diacetate 作用下， 以 乙腈 为溶剂， 以5%的产率得到benzyl 3-(8-hydroxynaphthalen-1-yl)prop-2-enoate
  参考文献：
  名称：

  Oxidative Coupling of NH Isoquinolones with Olefins Catalyzed by Rh(III)

  摘要：

  Rh(III)-catalyzed oxidative coupling reactions between isoquinolones with 3-aryl groups and activated olefins have been achieved using anhydrous Cu(OAc)(2) as an oxidant to give tetracyclic products. The nitrogen atom acts as a directing group to facilitate ortho C-H activation. This reaction can be one-pot starting from methyl benzohydroxamates, without the necessity of the isolation of isoquinolone products. Abroad scope of substrates has been demonstrated, and both terminal and internal activated olefins can be applied. In the coupling of N-methylmaleimide, a Wacker-like mechanism was proposed, where backside attack of the NH group in isoquinolones is suggested as a key step. Selective C-H activation has also been achieved at the 8-position of 1-naphthol, leading to an olefination product.

  DOI：

  10.1021/jo2002209