trans-5-(2-bromoanilino)-6-hydroxy-5,6-dihydro-1,10-phenanthroline | 142009-80-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: trans-5-(2-bromoanilino)-6-hydroxy-5,6-dihydro-1,10-phenanthroline
• CAS: 142009-80-1
• 化学式: C₁₈H₁₄BrN₃O
• 分子量: 368.233
• InChiKey: GCWWCWQGBQMCDV-ROUUACIJSA-N

物化性质

• 熔点：
  130 °C
• 沸点：
  595.2±50.0 °C(Predicted)
• 密度：
  1.596±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.11
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  58.04
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  trans-5-(2-bromoanilino)-6-hydroxy-5,6-dihydro-1,10-phenanthroline 在 manganese(IV) oxide 作用下， 以 氯仿 为溶剂， 以67%的产率得到N-(2-bromophenyl)-1,10-phenanthroline-5,6-quinone monoimine
  参考文献：
  名称：

  The synthesis of ascididemin

  摘要：

  A short synthesis of the pentacyclic marine alkaloid ascididemin 1 (four steps, 21% yield) from 1,10-phenanthroline 16 is described. The key step, photocyclisation of the quinoneimine 14 in sulphuric acid, is the first such aza stilbene photocyclisation of a quinoneimine. Intermediate 14 is prepared in a single, but low yielding, step from the quinone 4 in an aza Wadsworth-Emmons reaction, or in much better yield from the epoxide 17 by treatment with 2-iodoaniline and triethylaluminium, followed by oxidation with barium manganate.

  DOI：

  10.1016/s0040-4020(01)88497-0
• 作为产物：
  描述：

  邻菲罗啉 在 四丁基硫酸氢铵 industrial bleach (pH 8.2-8.3 with conc. HCl) 、 三乙基铝 作用下， 以 氯仿 、 水 为溶剂， 生成 trans-5-(2-bromoanilino)-6-hydroxy-5,6-dihydro-1,10-phenanthroline
  参考文献：
  名称：

  The synthesis of ascididemin

  摘要：

  A short synthesis of the pentacyclic marine alkaloid ascididemin 1 (four steps, 21% yield) from 1,10-phenanthroline 16 is described. The key step, photocyclisation of the quinoneimine 14 in sulphuric acid, is the first such aza stilbene photocyclisation of a quinoneimine. Intermediate 14 is prepared in a single, but low yielding, step from the quinone 4 in an aza Wadsworth-Emmons reaction, or in much better yield from the epoxide 17 by treatment with 2-iodoaniline and triethylaluminium, followed by oxidation with barium manganate.

  DOI：

  10.1016/s0040-4020(01)88497-0

文献信息

• Preparation of Chiral 5,6-trans-Disubstituted Phenanthrolines from Phenanthroline-5,6-epoxide
  作者：Elke Schoffers、Son Duc Tran、Kristen Mace

  DOI：10.3987/com-02-9689

  日期：——

  A new preparative route to chiral aminoalcohol derivatives of 5,6-dihydro-1,10-phenanthroline is described. Ring opening of 1,10-phenanthroline-5,6-epoxide (1) with a variety of nitrogen nucleophiles was accomplished using magnesium perchlorate as an effective Lewis acid and compared to reactions catalyzed by alumina.
• The synthesis of ascididemin
  作者：Christopher J. Moody、Charles W. Rees、Robert Thomas

  DOI：10.1016/s0040-4020(01)88497-0

  日期：1992.1

  A short synthesis of the pentacyclic marine alkaloid ascididemin 1 (four steps, 21% yield) from 1,10-phenanthroline 16 is described. The key step, photocyclisation of the quinoneimine 14 in sulphuric acid, is the first such aza stilbene photocyclisation of a quinoneimine. Intermediate 14 is prepared in a single, but low yielding, step from the quinone 4 in an aza Wadsworth-Emmons reaction, or in much better yield from the epoxide 17 by treatment with 2-iodoaniline and triethylaluminium, followed by oxidation with barium manganate.