6,7-Benzo-3,4-(1,4-dimethoxy-2,3-naphtho)-5-hydroxy-1-oxosuberane | 137789-73-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 二苯并环庚烯
• 英文名称: 6,7-Benzo-3,4-(1,4-dimethoxy-2,3-naphtho)-5-hydroxy-1-oxosuberane
• 英文别名: 2-hydroxy-12,19-dimethoxytetracyclo[9.8.0.03,8.013,18]nonadeca-1(19),3,5,7,11,13,15,17-octaen-9-one
• CAS: 137789-73-2
• 化学式: C₂₁H₁₈O₄
• 分子量: 334.372
• InChiKey: UUSUFYAFSBHUNB-UHFFFAOYSA-N

物化性质

• 沸点：
  562.1±50.0 °C(Predicted)
• 密度：
  1.288±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.68
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  6,7-Benzo-3,4-(1,4-dimethoxy-2,3-naphtho)-5-hydroxy-1-oxosuberane 在 三氯化铝 、 Celite 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 6,7-Benzo-3,4-(1,4-dimethoxy-2,3-naphtho)-1,2-dehydro-1-hydroxy-2-(3,3-dimethylacryloyl)-5-oxosuberane
  参考文献：
  名称：

  The Synthesis of Radermachol

  摘要：

  Five different approaches to the preparation of 6,7-benzo-3,4-(1,4-dimethoxy-2,3-naphtho)-1,5-dioxosuberane (3), an intermediate needed for the synthesis of radermachol (1), the red pigment from the roots of Radermachera xylocarpa, are described. The synthesis of radermachol (1) has been accomplished from 1,4-nephthoquinone in 14 steps.

  DOI：

  10.1021/jo00105a046
• 作为产物：
  描述：

  2-Benzyl-3-(bromomethyl)-1,4-dimethoxynaphthalene 在 氢氧化钾 、 N-溴代丁二酰亚胺(NBS) 、 水 、 过氧化苯甲酰 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 38.0h， 生成 6,7-Benzo-3,4-(1,4-dimethoxy-2,3-naphtho)-5-hydroxy-1-oxosuberane
  参考文献：
  名称：

  The Synthesis of Radermachol

  摘要：

  Five different approaches to the preparation of 6,7-benzo-3,4-(1,4-dimethoxy-2,3-naphtho)-1,5-dioxosuberane (3), an intermediate needed for the synthesis of radermachol (1), the red pigment from the roots of Radermachera xylocarpa, are described. The synthesis of radermachol (1) has been accomplished from 1,4-nephthoquinone in 14 steps.

  DOI：

  10.1021/jo00105a046

文献信息

• The total synthesis of radermachol
  作者：Qingping Jiang、Balawant S. Joshi、S. William Pelletier

  DOI：10.1016/s0040-4039(00)92365-7

  日期：1991.9

  The red pigment, radermachol (1), has been synthesized from 1,4-dimethoxynaphthelene in thirteen steps.
• Crystal and molecular structure of 6,7-benzo-3,4 (1,4-dimethoxy-2,3-naphtho)-1,5-dioxosuberane
  作者：Elizabeth M. Holt、Balawant S. Joshi、Qingping Jiang、S. William Pelletier

  DOI：10.1007/bf01665273

  日期：1995.7

  The crystal and molecular structure of the title compound (2) C21H16O4 has been determined by an X-ray analysis, by direct methods from diffractometer data and refined by full-matrix least squares. The compound (2) crystallizes in the space group P2(1)/a, with cell parameters: 36.432(5), b = 5.512(3), c = 8.269(5) Angstrom, beta = 108.0(3)degrees, z = 4, D-c = 1.397 g/cm(-3), R = 7.8 for 1136 observed reflections. The conformation of the tetracyclic ring system shows a folding of two planar parts of the carbon skeleton about an axis passing thorough C8 and C16 of the seven membered ring C.