(-)-(2S,9S)-2,9-diphenyl-1,2,3,4,7,8,9,10-octahydro-1,10-phenanthroline | 916900-90-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (-)-(2S,9S)-2,9-diphenyl-1,2,3,4,7,8,9,10-octahydro-1,10-phenanthroline
• 英文别名: (2S,9S)-2,9-diphenyl-1,2,3,4,7,8,9,10-octahydro-1,10-phenanthroline
• CAS: 916900-90-8
• 化学式: C₂₄H₂₄N₂
• 分子量: 340.468
• InChiKey: NWUIMGTVXDZCRZ-VXKWHMMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (-)-(2S,9S)-2,9-diphenyl-1,2,3,4,7,8,9,10-octahydro-1,10-phenanthroline 在 盐酸 、 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.83h， 生成 (-)-(3S,5S)-diphenyl-1,2,3,5,6,7-hexahydro-3a,4a-diazacyclopenta[def]phenanthren-4-thione
  参考文献：
  名称：

  Reduction of substituted 1,10-phenanthrolines as a route to rigid chiral benzimidazolylidenes

  摘要：

  Variously substituted 1,10-phenanthrolines are reduced to octahydrophenanthrolines in moderate to good yields with NaBH3CN in acetic acid/methanol. The exact solvent composition is important to avoid the formation of tetrahydrophenanthrolines and N-alkylated by-products, and to optimize the formation of octabydrophenanthrolines. Resolution of a racemic reduction product gives an enantiornerically pure C-2-symmetric diamine from which the corresponding rigid benzimidazolylidene is prepared, whereas reduction of chiral phenanthrolines derived from bicyclic ketones affords diastercomerically pure diamines, which may also be converted to benzimidazolylidenes. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.023
• 作为产物：
  描述：

  2,9-二苯基-1,10-菲咯啉 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 lithium aluminium tetrahydride 、 sodium cyanoborohydride 、 溶剂黄146 、 N,N-二甲基苯胺 、 三氯化磷 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 10.09h， 生成 (-)-(2S,9S)-2,9-diphenyl-1,2,3,4,7,8,9,10-octahydro-1,10-phenanthroline
  参考文献：
  名称：

  Reduction of substituted 1,10-phenanthrolines as a route to rigid chiral benzimidazolylidenes

  摘要：

  Variously substituted 1,10-phenanthrolines are reduced to octahydrophenanthrolines in moderate to good yields with NaBH3CN in acetic acid/methanol. The exact solvent composition is important to avoid the formation of tetrahydrophenanthrolines and N-alkylated by-products, and to optimize the formation of octabydrophenanthrolines. Resolution of a racemic reduction product gives an enantiornerically pure C-2-symmetric diamine from which the corresponding rigid benzimidazolylidene is prepared, whereas reduction of chiral phenanthrolines derived from bicyclic ketones affords diastercomerically pure diamines, which may also be converted to benzimidazolylidenes. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.023