cis/trans-1-(1,4,5,8-tetramethoxynaphthyl-2)-2-(2-hydroxypropyl-2)cyclopropane

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: cis/trans-1-(1,4,5,8-tetramethoxynaphthyl-2)-2-(2-hydroxypropyl-2)cyclopropane
• 英文别名: 2-[2-(1,4,5,8-tetramethoxynaphthalen-2-yl)cyclopropyl]propan-2-ol
• 化学式: C₂₀H₂₆O₅
• 分子量: 346.423
• InChiKey: JLPRKYGUTRKYDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  cis/trans-1-(1,4,5,8-tetramethoxynaphthyl-2)-2-(2-hydroxypropyl-2)cyclopropane 在 silver(II) oxide 、 高氯酸 、 ammonium cerium(IV) nitrate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 乙腈 为溶剂， 反应 30.66h， 生成 紫朱牛舌草(ALKANNATINCTORIA)根提取物
  参考文献：
  名称：

  Synthesis of shikalkin and certain related compounds

  摘要：

  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.

  DOI：

  10.1007/bf00864352

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.