(1R,5S)-(2,3-b)-pineno-1,10-phenanthroline | 204776-66-9

• 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: (1R,5S)-(2,3-b)-pineno-1,10-phenanthroline
• 英文别名: (1S,5R)-(-)-(2,3-b)-pineno-1,10-phenanthroline；9,11-Methanobenzo[b][1,10]phenanthroline, 8,9,10,11-tetrahydro-10,10-dimethyl-, (9S,11S)-；(1S,17S)-18,18-dimethyl-3,6-diazapentacyclo[15.1.1.02,15.04,13.05,10]nonadeca-2(15),3,5(10),6,8,11,13-heptaene
• CAS: 204776-66-9
• 化学式: C₁₉H₁₈N₂
• 分子量: 274.365
• InChiKey: KXQGYTZHFQLASZ-HUUCEWRRSA-N

物化性质

• 沸点：
  457.4±40.0 °C(Predicted)
• 密度：
  1.202±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,5S)-(2,3-b)-pineno-1,10-phenanthroline 在 盐酸 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 21.0h， 生成
  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：

  (-)-诺蒎酮 、 8-胺基-7-醛基喹啉 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 5.0h， 以85%的产率得到(1R,5S)-(2,3-b)-pineno-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

文献信息

• Diastereoselective Formation and Photophysical Behavior of a Chiral Copper(I) Phenanthroline Complex
  作者：Elvira C. Riesgo、Alberto Credi、Luisa De Cola、Randolph P. Thummel

  DOI：10.1021/ic971267a

  日期：1998.5.1

  identical MLCT absorptions at 442 nm. Both complexes are nonemissive at 298 and 77 K. Stern-Volmer quenching studies were carried out with optically pure Delta- and Lambda-[Ru(bpy)(3)](2+) and racemic [Ru(dpb)(3)](2+) as donors (bpy = 2,2'-bipyridine and dpb = 4,4'-diphenyl-bpy). Neither study provides any evidence of enantioselective quenching, indicating that energy or electron transfer may be occurring

  （1R，5S）-（+）-和（1S，5R）-（-）-nopinone与8-氨基喹啉-7-甲醛的Friedländer缩合反应生成对映体纯的（2,3-b）-pineno- 1,10-菲咯啉。这些配体与Cu（I）的配位提供了不可相互转化的手性络合物，在其CD光谱中显示出相同和相反的Cotton效应，以及+0.37 V的相同半波氧化电位和442 nm处的MLCT吸收。两种络合物在298和77 K时均无发射。用光学纯的Delta-和Lambda- [Ru（bpy）（3）]（2+）和外消旋[Ru（dpb）（3）]进行Stern-Volmer猝灭研究。 （2+）作为供体（bpy = 2,2'-联吡啶和dpb = 4,4'-二苯基-bpy）。两项研究均未提供对映选择性淬灭的任何证据，
• Reduction of substituted 1,10-phenanthrolines as a route to rigid chiral benzimidazolylidenes
  作者：Costa Metallinos、Fred B. Barrett、Yao Wang、Shufen Xu、Nicholas J. Taylor

  DOI：10.1016/j.tet.2006.09.023

  日期：2006.11

  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.