2-(1'-hydroxy-4'-methylpent-3'-en-1'-yl)-5,8-dimethoxy-1,4-naphthaquinone | 145668-25-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(1'-hydroxy-4'-methylpent-3'-en-1'-yl)-5,8-dimethoxy-1,4-naphthaquinone
• 英文别名: 2-(1'-hydroxy-4'-methylpent-3'-en-1'-yl)-5,8-dimethoxy-1,4-naphthoquinone；2-(1-Hydroxy-4-methylpent-3-enyl)-5,8-dimethoxynaphthalene-1,4-dione
• CAS: 145668-25-3
• 化学式: C₁₈H₂₀O₅
• 分子量: 316.354
• InChiKey: GXKBSCZWXXVZIU-UHFFFAOYSA-N

物化性质

• 沸点：
  514.2±50.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(1'-hydroxy-4'-methylpent-3'-en-1'-yl)-5,8-dimethoxy-1,4-naphthaquinone 在 4-二甲氨基吡啶 、 sodium dithionite 、 ammonium cerium(IV) nitrate 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 6.58h， 生成 紫草素
  参考文献：
  名称：

  A New Efficient Route for Multigram Asymmetric Synthesis of Alkannin and Shikonin

  摘要：

  A short and convergent approach for the synthesis of alkannin, shikonin and shikalkin is presented. A Hauser-type annulation of cyanophthalide 26 with enone 7 affords the complete aromatic system in just one step with concomitant attachment of the entire side chain. Subsequent Corey's oxazaborolidine mediated asymmetric reduction of the above advanced intermediate, leads to the required isomer in high enantiomeric excess. Finally, a selective and high yielding deprotection protocol furnishes the title compounds as pure crystalline precipitates. Thus, a multigram synthesis of shikonin, alkannin and shikalkin is achieved in high yield and enantioselectivity.

  DOI：

  10.1002/1521-3765(20020415)8:8<1795::aid-chem1795>3.0.co;2-v
• 作为产物：
  描述：

  2-(1-hydroxy-4-methyl-3-pentenyl)-1,4,5,8-tetramethoxynaphthalene 生成 2-(1'-hydroxy-4'-methylpent-3'-en-1'-yl)-5,8-dimethoxy-1,4-naphthaquinone
  参考文献：
  名称：

  MOISEENKOV, A. M.;BALANEVA, N. N.;NOVIKOV, V. L.;ELYAKOV, G. B., DOKL. AN CCCP, 295,(1987) N 3, 614-617

  摘要：

  DOI：

文献信息

• Synthesis of shikalkin and certain related compounds
  作者：V. L. Novikov、N. N. Balaneva、A. M. Moiseenkov、G. B. Elyakov

  DOI：10.1007/bf00864352

  日期：1992.8

  A successful total synthesis of a biologically active pigment from plants of the Boraginaceae family was carried out with naphthazarine as the starting material, and using the 1,4,5,8-tetramethoxynaphthalene, the corresponding 2-vinyl derivative and its epoxide or a cyclopropane adduct with diazoacetic ester at the key stages. In the course of developing the scheme of the synthesis of shikalkin, its three analogs were obtained, differing in the nature of the monoterpenoid side chain.
• Moiseenkov, A. M.; Balaneva, H. N.; Novikov, V. L., Doklady Chemistry, 1987, vol. 295, # 7, p. 320 - 322
  作者：Moiseenkov, A. M.、Balaneva, H. N.、Novikov, V. L.、Elyakov, G. B.

  DOI：——

  日期：——