Spinochrom E-hexaacetat | 96260-21-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Spinochrom E-hexaacetat
• CAS: 96260-21-8
• 化学式: C₂₂H₁₈O₁₄
• 分子量: 506.377
• InChiKey: IFISGUNWSPUYJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  36.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  191.94
• 氢给体数：
  0.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  Spinochrom E-hexaacetat 在 水 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 以76%的产率得到2,5,6,7,8-pentaacetoxy-3-hydroxynaphthalene-1,4-dione
  参考文献：
  名称：

  Preparative Monomethylation of 2,3,5,6,7,8-Hexahydroxynaphthalene-1,4-dione (Spinochrome E). The First Direct Synthesis of Namakochrome: the Natural Pigment of the Holothurian Polycheira rufescens

  摘要：

  A 4-step preparative conversion of the available sea urchins pigment spinochrome E into the holothurian Polycheira rufescens pigment namakochrome was developed. Spinochrome E was converted into hexaacetate, and one beta-acetate group in the quinone core of the latter was selectively removed. The resulting pentaacetate was treated with diazomethane, and all protective acetate groups were removed by treatment with methanolic HCl. The total yield of namakochrome over 4 steps was similar to 46-51%.

  DOI：

  10.1134/s1070428020020050
• 作为产物：
  描述：

  spinochrome E 、 乙酸酐 在 硫酸 作用下， 反应 5.0h， 以85%的产率得到Spinochrom E-hexaacetat
  参考文献：
  名称：

  Preparative Monomethylation of 2,3,5,6,7,8-Hexahydroxynaphthalene-1,4-dione (Spinochrome E). The First Direct Synthesis of Namakochrome: the Natural Pigment of the Holothurian Polycheira rufescens

  摘要：

  A 4-step preparative conversion of the available sea urchins pigment spinochrome E into the holothurian Polycheira rufescens pigment namakochrome was developed. Spinochrome E was converted into hexaacetate, and one beta-acetate group in the quinone core of the latter was selectively removed. The resulting pentaacetate was treated with diazomethane, and all protective acetate groups were removed by treatment with methanolic HCl. The total yield of namakochrome over 4 steps was similar to 46-51%.

  DOI：

  10.1134/s1070428020020050

文献信息

• 204. Naturally occurring quinones. Part V. Spinochromes E and N
  作者：J. Smith、R. H. Thomson

  DOI：10.1039/jr9610001008

  日期：——
• Preparative Monomethylation of 2,3,5,6,7,8-Hexahydroxynaphthalene-1,4-dione (Spinochrome E). The First Direct Synthesis of Namakochrome: the Natural Pigment of the Holothurian Polycheira rufescens
  作者：S. G. Polonik、V. A. Denisenko、R. S. Popov、A. A. Artjukov、Y. E. Sabutskii

  DOI：10.1134/s1070428020020050

  日期：2020.2

  A 4-step preparative conversion of the available sea urchins pigment spinochrome E into the holothurian Polycheira rufescens pigment namakochrome was developed. Spinochrome E was converted into hexaacetate, and one beta-acetate group in the quinone core of the latter was selectively removed. The resulting pentaacetate was treated with diazomethane, and all protective acetate groups were removed by treatment with methanolic HCl. The total yield of namakochrome over 4 steps was similar to 46-51%.