(6aR,9R,9aS,9bS)-4-benzyl-9b-methoxy-9-methyl-3,6a,9,9a-tetrahydro-2H-pyrazolo[3,4-h][1,4]benzoxazin-6-one | 145134-16-3

• 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: (6aR,9R,9aS,9bS)-4-benzyl-9b-methoxy-9-methyl-3,6a,9,9a-tetrahydro-2H-pyrazolo[3,4-h][1,4]benzoxazin-6-one
• CAS: 145134-16-3
• 化学式: C₁₈H₂₁N₃O₃
• 分子量: 327.383
• InChiKey: XJPSEGLAVXWXEP-PBZHRCKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  63.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  重氮乙烷 、 4-Benzyl-8a-methoxy-3,4-dihydro-2H-1,4-benzoxazin-6(8aH)-on 以 甲醇 、 乙醚 为溶剂， 反应 12.0h， 以13%的产率得到4-Benzyl-9b-methoxy-9-methyl-3,4,8,9,9a,9b-hexahydro-pyrazolo<3,4-h><1,4>benzoxazin-6(2H)-on
  参考文献：
  名称：

  Zur Umsetzung von 8a-Methoxy-3,4-dihydro-2H-1,4-benzoxazin-6(8aH)-onen mit Diazoalkanen, 2. Mitt.

  摘要：

  8a-Methoxy-3,4-dihydro-2H-1,4-benzoxazin-6(8aH)-ones 2 undergo regio- and stereospecific 1,3-dipolar cycloaddition reactions with diazomethane or diazoethane to yield 3,4,6 a,9,9 a,9 b-hexahydro-pyrazolo[3,4-h][1,4]benzoxazin-6(2H)-ones 3, which slowly isomerize in solution to give the 3,4,8,9,9a,9b-hexahydro-pyrazolo[3,4-h][1,4]benzoxazin-6(2H)-ones 5. The carbon of the diazoalkane dipole is attached to carbon C-8 of the benzoxazinone. The structures of the obtained products were determined by H-1- and C-13-NMR spectroscopy. An X-ray crystal structure analysis of 3a was carried out at room temperature: C11H15N3O3, M(r) = 237.26, orthorhombic, Pc2(1)n, a = 9.173 (5), b = 9.133 (4), c = 13.281 (6), V = 1112.6 (9) angstrom3, Z = 4, d(x) = 1.416 g/cm-3, mu = 0.93 cm-1, R = 4.33%, R(w) = 3.95% (919 observations, 168 parameters).

  DOI：

  10.1007/bf00811545

文献信息

• Zur Umsetzung von 8a-Methoxy-3,4-dihydro-2H-1,4-benzoxazin-6(8aH)-onen mit Diazoalkanen, 2. Mitt.
  作者：Manfred Schubert-Zsilavecz、Ferdinand Belaj、Robert Ott

  DOI：10.1007/bf00811545

  日期：1992.10

  8a-Methoxy-3,4-dihydro-2H-1,4-benzoxazin-6(8aH)-ones 2 undergo regio- and stereospecific 1,3-dipolar cycloaddition reactions with diazomethane or diazoethane to yield 3,4,6 a,9,9 a,9 b-hexahydro-pyrazolo[3,4-h][1,4]benzoxazin-6(2H)-ones 3, which slowly isomerize in solution to give the 3,4,8,9,9a,9b-hexahydro-pyrazolo[3,4-h][1,4]benzoxazin-6(2H)-ones 5. The carbon of the diazoalkane dipole is attached to carbon C-8 of the benzoxazinone. The structures of the obtained products were determined by H-1- and C-13-NMR spectroscopy. An X-ray crystal structure analysis of 3a was carried out at room temperature: C11H15N3O3, M(r) = 237.26, orthorhombic, Pc2(1)n, a = 9.173 (5), b = 9.133 (4), c = 13.281 (6), V = 1112.6 (9) angstrom3, Z = 4, d(x) = 1.416 g/cm-3, mu = 0.93 cm-1, R = 4.33%, R(w) = 3.95% (919 observations, 168 parameters).